Facile synthesis of new 1,2,3-benzotriazolo-2-oxo-azetidine analogues by microwave irradiation

Ritu Sharma; Savitri D. Srivastava; Santosh K. Srivastava; Pushkal Samadhiya

doi:10.1016/j.arabjc.2010.06.035

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Original Article

4 (

); 179-184

doi:

10.1016/j.arabjc.2010.06.035

Facile synthesis of new 1,2,3-benzotriazolo-2-oxo-azetidine analogues by microwave irradiation

Ritu Sharma, Savitri D. Srivastava, Santosh K. Srivastava, Pushkal Samadhiya^*

Synthetic Organic Chemistry Laboratory, Department of Chemistry, Dr. H.S. Gour University (A Central University), Sagar, M.P. 470 003, India

*Corresponding author pushkalsamadhiya@rediffmail.com (Pushkal Samadhiya)

Received: 2010-6-16, Accepted: 2010-6-17, Published: 2010-04-01

Disclaimer:
This article was originally published by Elsevier and was migrated to Scientific Scholar after the change of Publisher.

Peer review under responsibility of King Saud University.

Available online 11 July 2010

Abstract

A series of new N¹-[3-{(4-subtitutedaryl-3-chloro-2-oxo-azetidine)-carbamyl}-propyl]-1,2,3-benzotriazoles 4(a–s) have been synthesized from 1,2,3-benzotriazole as a starting material by microwave method. The structures of all the synthesized compounds were confirmed by chemical and spectral analyses such as IR, ¹H NMR, ¹³C NMR and FAB-Mass.

Keywords

Microwave synthesis of 1,2,3-benzotriazole

Azetidinone

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1 Introduction

Heterocycles are very important class of chemistry and interesting field for research. This field has great opportunities for the synthesis of novel drugs. Here we are reporting the synthesis of a series of 2-oxo-azetidine derivatives of 1,2,3-benzotriazole. 2-oxo-azetidine ring shows various biological activities such as antifungal (Shukla and Srivastava, 2008; Rawat and Srivastava, 1998; Chavan and Pai, 2007; Singh et al., 2007 ), antibacterial (Nema and Srivastava, 2007; Mulwad et al., 2008; Van der Steen and Koten, 1991; Singh, 2004 ), antitubercular (Parikh et al., 2000, 2005; Patel et al., 2006 ), anticonvulsant (Srivastava et al., 2000), analgesic, anti-inflammatory (Srivastava et al., 1999), synthetic precursor for amino acids (Alonsodel et al., 2002), and antiviral (Skiles and McNeil, 1990).

Benzotriazole derivatives have broad range of biological activities such as antibacterial (Asati et al., 2006), antifungal (Nema and Srivastava, 2007; Lebouvier et al., 2006), antihistaminic, antiadrenergic and analgesic (Caliendo et al., 1995), DNA cleavage (Annapukowska et al., 2006), and antitubercular (Sanna et al., 2000). Nowadays microwave synthesis is suitable and is a favorite technique of the researcher for synthesis because it is eco-friendly, controls pollution, converts hours into minutes, enhances yield and stops wastage of solvents; so it has economical importance and also helps to stop global warming. The structures of all the newly synthesized compounds were confirmed by elemental analysis IR, ¹H NMR, ¹³C NMR and FAB-Mass.

Scheme for the synthesis of compounds 1, 2, 3(a–s), 4(a–s).

Comp.	Ar	Comp.	Ar	Comp.	Ar
3a, 4a	C₆H₅	3h, 4h	4-NO₂C₆H₄	3o, 4o	2-CH₃OC₆H₄
3b, 4b	4-ClC₆H₄	3i, 4i	3-NO₂C₆H₄	3p, 4p	2-CH₃OC₆H₄
3c, 4c	3-ClC₆H₄	3j, 4j	2-NO₂C₆H₄	3q, 4q	4-HOC₆H₄
3d, 4d	2-ClC₆H₄	3k, 4k	4-CH₃OC₆H₄	3r, 4r	3-HOC₆H₄
3e, 4e	4-BrC₆H₄	3l, 4l	3-CH₃OC₆H₄	3s, 4s	2-HOC₆H₄
3f, 4f	3-BrC₆H₄	3m, 4m	2-CH₃OC₆H₄	–	–
3g, 4g	2-BrC₆H₄	3n, 4n	4-CH₃C₆H₄	–	–

2 Materials and methods

2.1

2.1 Experimental

Melting points were taken in open capillaries and are uncorrected. Progress of reaction was monitored by silica gel-G coated TLC plates using MeOH: CHCl₃ system (1:9). The spot was visualized by exposing the dry plate to iodine vapours chamber. IR spectra were recorded in KBr disc on a Schimadzu 8201 PC, FTIR spectrophotometer (ν_max in cm⁻¹) and ¹H NMR and ¹³C NMR spectra were measured on a Brucker DRX-300 spectrometer in CDCl₃ at 300 MHz using TMS as an internal standard. All chemical shifts were reported on δ scales. The FAB mass spectra were recorded on a Jeol SX-102 mass spectrometer. Elemental analyses were performed on a Carlo Erba-1108 analyzer. Microwave irradiation was carried out in an open glass vessel. Modified microwave oven (800 W) was used for the synthesis of the compounds. A thermocouple was used to monitor the temperature inside the vessel of the microwave. The analytical data of all the compounds were highly satisfactory. For column chromatographic purification of the products, Merck silica Gel 60 (230–400 Mesh) was used. The reagent grade chemicals were purchased from the commercial sources and further purified before use (see Table 1).

Table 1 Spectral data of compounds 1, 2, 3(a–s) and 4(a–s).

Comp.	IR (cm⁻¹)	¹H NMR	¹³C NMR	FAB mass
1	745 (C–Cl), 1232 (N–CH₂), 1560 (C⚌C), 3018, 2838 (CH)	1.81 (p, 2H, J = 7.45 Hz, CH₂CH₂CH₂), 3.44 (t, 2H, J = 7.45 Hz, CH₂CH₂CH₂–Cl), 3.72 (t, 2H, J = 7.45 Hz, N–CH₂CH₂CH₂), 7.26–7.95 (m, 4H, Ar)	36.4 (CH₂CH₂CH₂), 43.8 (CH₂CH₂CH₂–Cl), 49.1 (N–CH₂CH₂CH₂), 118.7, 120, 128.1, 128.7, 145, 147.7 (6C, Ar)	196M⁺
2	1230 (C–N), 1652 (C⚌O), 3348 (NH), 3430 (NH₂)	1.71 (p, 2H, J = 7.42 Hz, CH₂CH₂CH₂), 3.28 (t, 2H, J = 7.42 Hz, CH₂CH₂CH₂–NH), 3.81 (t, 2H, J = 7.42 Hz, N–CH₂CH₂CH₂), 5.60 (s, 1H, NH), 5.88 (s, 2HNH₂), 6.86–7.72 (m, 4H, Ar)	39.7 (CH₂CH₂CH₂), 43.1 (CH₂CH₂CH₂NH), 48.7 (N–CH₂CH₂CH₂), 163.4 (CO), 117.9, 121.1, 127.7, 128.2, 144.7, 46.8 (6C, Ar)	219M⁺
3a	1551 (N⚌CH), 1660 (C⚌O), 3362 (NH)	1.64 (p, 2H, J = 7.35Hz, CH₂CH₂CH₂), 3.32 (t, 2H, J = 7.35Hz, CH₂CH₂CH₂–NH), 3.72 (t, 2H, J = 7.35Hz, N–CH₂CH₂CH₂), 5.76 (s, 1H, NH), 7.84 (s, 1H, N⚌CH), 7.40–7.71 (m, 9H, Ar)	38.2 (CH₂CH₂CH₂), 45.2 (CH₂CH₂CH₂–N), 51.1 (N–CH₂CH₂CH₂), 145 (N⚌CH), 162.7 (CO), 120, 120.9, 125.7, 126, 127.1, 128.3, 129, 129.2, 131.2, 138, 146, 149 (12C, Ar)	307M⁺
3b	738 (C–Cl), 1562 (N⚌CH), 1670 (C⚌O), 3370 (NH)	1.76 (p, 2H, J = 7.35 Hz, CH₂CH₂CH₂), 3.38 (t, 2H, J = 7.35 Hz, CH₂CH₂CH₂–NH), 3.81 (t, 2H, J = 7.35 Hz, N–CH₂CH₂CH₂), 5.75 (s, 1H, NH), 7.91 (s, 1H, N⚌CH), 7.28–7.81 (m, 8H, Ar)	38.9 (CH₂CH₂CH₂), 44.4 (CH₂CH₂CH₂–NH), 47.1 (N–CH₂CH₂CH₂), 152 (N⚌CH), 166 (CO), 120.4, 127.1, 127.7, 128.8, 129, 130, 131, 131.2, 133.3, 137.8, 143.1, 144.2 (12C, Ar)	341M⁺
3c	736 (C–Cl), 1559 (N⚌CH), 1673 (C⚌O), 3365 (NH)	1.73 (p, 2H, J = 7.38 Hz, CH₂CH₂CH₂), 3.36 (t, 2H, J = 7.38 Hz, CH₂CH₂CH₂–NH), 3.79 (t, 2H, J = 7.38 Hz, N–CH₂CH₂CH₂), 5.77 (s, 1H, NH), 7.97 (s, 1H, N⚌CH), 7.1–7.9 (m, 8H, Ar)	38.5 (CH₂CH₂CH₂), 43.5 (CH₂CH₂CH₂–N), 52 (N–CH₂CH₂CH₂), 158.2 (N⚌CH), 167.6 (CO), 117, 120, 125.3, 126.4, 128.3, 129.4, 131, 132.5, 135.6, 140, 146.1, 144.9 (12C, Ar)	341M⁺
3d	730 (C–Cl), 1566 (N⚌CH), 1673 (C⚌O), 3371 (NH)	1.69 (p, 2H, J = 7.40 Hz, CH₂CH₂CH₂), 3.30 (t, 2H, J = 7.40 Hz, CH₂CH₂CH₂–NH), 3.84 (t, 2H, J = 7.40 Hz, N–CH₂CH₂CH₂), 5.73 (s, 1H, NH), 8.07 (s, 1H N⚌CH), 7.2–7.9 (m, 8H, Ar)	38.7 (CH₂CH₂CH₂), 44.2 (CH₂CH₂CH₂–N), 50 (N–CH₂CH₂CH₂), 155.6 (N⚌CH), 166.9 (CO), 116.4, 122.8, 125, 126.7, 128, 129.2, 130.5, 131, 134, 137.8, 141.2, 147.2 (12C, Ar)	341M⁺
3e	636 (C-Br), 1562 (N⚌CH), 1667 (C⚌O), 3374 (NH)	1.67 (p, 2H, J = 7.50 Hz, CH₂CH₂CH₂), 3.31 (t, 2H, J = 7.50 Hz, CH₂CH₂CH₂–NH), 3.79 (t, 2H, J = 7.50 Hz, N–CH₂CH₂CH₂), 5.78 (s, 1H, NH), 7.97 (s, 1H, N⚌CH) 7.39–7.68 (m, 8H, Ar)	36.1 (CH₂CH₂CH₂), 44.2 (CH₂CH₂CH₂–NH), 50.2 (N–CH₂CH₂CH₂), 154 (N⚌CH), 163.1 (CO), 119, 121, 124, 127, 128.4, 129, 130, 134, 139, 141.3, 148, 150 (12C, Ar)	386M⁺
3f	641 (C–Br), 1562 (N⚌CH), 1661 (C⚌O), 3366 (NH)	1.64 (p, 2H, J = 7.52 Hz, CH₂CH₂CH₂), 3.27 (t, 2H, J = 7.52 Hz, CH₂CH₂CH₂–NH), 3.83 (t, 2H, J = 7.52 Hz, N–CH₂CH₂CH₂), 5.72 (s, 1H, NH), 7.98 (s, 1H, N⚌CH) 7.23–7.9 (m, 8H, Ar)	36.3 (CH₂CH₂CH₂), 44.4 (CH₂CH₂CH₂–N), 48 (NCH₂CH₂CH₂), 151.6 (N⚌CH), 163.9 (CO), 116, 119.6, 125.2, 126.8, 128, 129.3, 131.1, 136, 138.6, 143.1, 147.3, 152 (12C, Ar)	386M⁺
3g	628 (C–Br), 1558 (N⚌CH), 1672 (C⚌O), 3367 (NH)	1.71 (p, 2H, J = 7.55 Hz, CH₂CH₂CH₂), 3.31 (t, 2H, J = 7.55 Hz, CH₂CH₂CH₂–NH), 3.77 (t, 2H, J = 7.55 Hz, N–CH₂CH₂CH₂), 5.69 (s, 1H, NH), 8.02 (s, 1H, N⚌CH), 7.31–7.63 (m, 8H, Ar)	38.5 (CH₂CH₂CH₂), 44.1 (CH₂CH₂CH₂–NH), 51.4 (N–CH₂CH₂CH₂), 152 (N⚌CH), 164.1 (CO), 117.4, 121.5, 125.7, 127, 128, 129.4, 132, 137, 1140.2, 143.3, 147, 151 (12C, Ar)	386M⁺
3h	847 (C–N), 1528 (N⚌O), 1568 (N⚌CH), 1638 (C⚌O), 3358 (NH)	1.77 (p, 2H, J = 7.62 Hz, CH₂CH₂CH₂), 3.29 (t, 2H, J = 7.62 Hz, CH₂CH₂CH₂–NH), 3.84 (t,2H, J = 7.62 Hz, N–CH₂CH₂CH₂), 5.81 (s, 1H, NH), 8.10 (s, 1H, N⚌CH), 7.32–7.91 (m, 8H, Ar)	40.7 (CH₂CH₂CH₂), 45.3 (CH₂CH₂CH₂–N), 50.3 (NCH₂CH₂CH₂), 155.9 (N⚌CH), 162.4 (CO), 109, 110, 120.4, 121, 123, 128, 133, 135.6, 138.1, 141, 144, 149 (12C, Ar)	352M⁺
3i	848 (C–N), 1524 (N⚌O), 1572 (N⚌CH), 1635 (C⚌O), 3351 (NH)	1.68 (p, 2H, J = 7.60 Hz, CH₂CH₂CH₂), 3.16 (t, 2H, J = 7.60 Hz, CH₂CH₂CH₂–NH), 3.72 (t, 2H, J = 7.60 Hz, N–CH₂CH₂CH₂), 5.82 (s, 1H, NH), 8.08 (s, 1H, N⚌CH), 7.21–7.86 (m, 8H, Ar)	40.7 (CH₂CH₂CH₂), 44.2 (CH₂CH₂CH₂–NH), 49.1 (N–CH₂CH₂CH₂), 154.7 (N⚌CH), 163.2 (CO), 111, 114, 119.4, 121.4, 124, 129, 133.3, 135, 138.5, 140, 145, 151 (12C, Ar)	352M⁺
3j	842 (C–N), 1531 (N⚌O), 1575 (N⚌CH), 1644 (C⚌O), 3351 (NH)	1.74 (p, 2H, J = 7.60 Hz, CH₂CH₂CH₂), 3.25 (t, 2H, J = 7.60 Hz, CH₂CH₂CH₂–NH), 3.72 (t, 2H, J = 7.60 Hz, N–CH₂CH₂CH₂), 5.83 (s, 1H, NH), 8.17 (s, 1H, N⚌CH), 7.26–7.99 (m, 8H, Ar)	40.1 (CH₂CH₂CH₂), 45.1 (CH₂CH₂CH₂–N), 48.7 (NCH₂CH₂CH₂), 155.1 (N⚌CH), 162 (CO), 110.2, 115, 120, 121.6, 125, 126, 132, 135.5, 138.9, 142, 144.2, 151 (12C, Ar)	352M⁺
3k	1561 (N⚌CH), 2945 (OCH₃), 3351 (NH)	1.71 (p, 2H, J = 7.55 Hz, CH₂CH₂CH₂), 3.28 (t, 2H, J = 7.55 Hz, CH₂CH₂CH₂–NH), 3.50 (s, 3H, OCH₃), 3.63 (t, 2H, J = 7.55 Hz, NCH₂CH₂CH₂), 5.71 (s, 1H, NH), 7.85 (s, 1H, N⚌CH), 7.34–7.52 (m, 8H, Ar)	37.2 (CH₂CH₂CH₂), 42.6 (CH₂CH₂CH₂–NH), 47 (N–CH₂CH₂CH₂), 51.7 (OCH₃), 154.2 (N⚌CH), 160.5 (CO), 111.3, 114.5, 115, 118, 119.6, 122, 128, 131, 135.1, 146, 151, 158 (12C, Ar)	337M⁺
3l	1557 (N⚌CH), 2943 (OCH₃), 3358 (NH)	1.68 (p, 2H, J = 7.60 Hz, CH₂CH₂CH₂), 3.31 (t, 2H, J = 7.60 Hz, CH₂CH₂CH₂–NH), 3.61 (s, 3H, OCH₃), 3.68 (t, 2H, J = 7.60 Hz, N–CH₂CH₂CH₂), 5.69 (s, 1H NH), 7.96 (s, 1H, N⚌CH), 7.41–7.82 (m, 8H, Ar)	37.7 (CH₂CH₂CH₂), 42.9 (CH₂CH₂CH₂–NH), 47.7 (N–CH₂CH₂CH₂), 54.7 (OCH₃), 153.7 (N⚌CH), 161.9 (CO), 110.2, 114.1, 115.4, 117, 119, 120.3, 129.7, 132, 136.4, 142, 148, 158.7 (12C, Ar)	337M⁺
3m	1559 (N⚌CH), 2947 (OCH₃), 3361 (NH)	1.72 (p, 2H, J = 7.60 Hz, CH₂CH₂CH₂), 3.30 (t, 2H, J = 7.60 Hz, CH₂CH₂CH₂–NH), 3.67 (s, 3H, OCH₃), 3.75 (t, 2H, J = 7.60 Hz, N–CH₂CH₂CH₂), 5.74 (s, 1H, NH), 7.86 (s, 1H, N⚌CH), 7.22–7.72 (m, 8H, Ar)	38.1 (CH₂CH₂CH₂), 43.1 (CH₂CH₂CH₂–NH), 53.7 (OCH₃), 48.1 (N–CH₂CH₂CH₂), 151 (N⚌CH), 158.1 (CO), 113.2, 114.8, 117.4, 118, 119.5, 122, 127.7, 132.6, 135, 145, 147.4, 157.3 (12C, Ar)	337M⁺
3n	1549 (N⚌CH), 2917 (CH₃), 3340 (NH)	1.61 (p, 2H, J = 7.40 Hz, CH₂CH₂CH₂), 2.64 (s, 3H, CH₃), 3.22 (t, 2H, J = 7.40 Hz, CH₂CH₂CH₂–NH), 3.72 (t, 2H, J = 7.40 Hz, N–CH₂CH₂CH₂), 5.62 (s, 1H, NH), 7.89 (s, 1H, N⚌CH), 7.39–7.79 (m, 8H, Ar)	24.9 (CH₃), 36.6 (CH₂CH₂CH₂), 42.4 (CH₂CH₂CH₂–NH), 46.7 (N–CH₂CH₂CH₂), 151.2 (N⚌CH), 160.8 (CO), 120, 121.5, 123, 127.3, 128.9, 130.7, 131.7, 136, 138, 142.1, 145, 146.3 (12C, Ar)	321M⁺
3o	1544 (N⚌CH), 2921 (CH₃), 3345 (NH)	1.63 (p, 2H, J = 7.42 Hz, CH₂CH₂CH₂), 2.58 (s, 3H, CH₃), 3.13 (t, 2H, J = 7.42 Hz, CH₂CH₂CH₂–NH), 3.75 (t, 2H, J = 7.42 Hz, N–CH₂CH₂CH₂), 5.69 (s, 1H, NH), 7.91 (s, 1H, N⚌CH), 7.31–7.83 (m, 8H, Ar)	22.9 (CH₃), 36.7 (CH₂CH₂CH₂), 42.1 (CH₂CH₂CH₂–NH), 45.7 (N–CH₂CH₂CH₂), 152 (N⚌CH), 159.8 (CO), 118, 121, 125, 126, 128.1, 130.2, 132, 136.6, 140, 143, 144.5, 147 (12C, Ar)	321M⁺
3p	1551 (N⚌CH), 2908 (CH₃), 3341 (NH)	1.65 (p, 2H, J = 7.40 Hz, CH₂CH₂CH₂), 2.60 (s, 3H, CH₃), 3.24 (t, 2H, J = 7.40 Hz, CH₂CH₂CH₂–NH), 3.64 (t, 2H, J = 7.40 Hz, N–CH₂CH₂CH₂), 5.62 (s, 1H, NH), 7.88 (s, 1H, N⚌CH), 7.34–7.76 (m, 8H, Ar)	21.9 (CH₃), 38.2 (CH₂CH₂CH₂), 43.3 (CH₂CH₂CH₂–NH), 45.7 (N–CH₂CH₂CH₂), 154 (N⚌CH), 161.2 (CO), 119, 120.5, 124.5, 126.1, 126.1, 131.9, 131.7, 135, 139, 143, 144, 145 (12C, Ar)	321M⁺
3q	1557 (N⚌CH), 3385 (NH), 3472 (OH)	1.80 (p, 2H, J = 7.65 Hz, CH₂CH₂CH₂), 3.37 (t, 2H, J = 7.65 Hz, CH₂CH₂CH₂–NH), 3.71 (t, 2H, J = 7.65 Hz, N–CH₂CH₂CH₂), 4.15 (s, 1H, OH), 5.82 (s, 1H, NH), 8.07 (s, 1H, N⚌CH), 7.32–7.79 (m, 8H, Ar)	39.9 (CH₂CH₂CH₂), 45.3 (CH₂CH₂CH₂–NH), 50.1 (N–CH₂CH₂CH₂), 153.3 (N⚌CH), 166.7 (CO), 117, 118.9, 120.7, 122.7, 125.9, 128.4, 129.8, 132.2, 142.3, 146.9, 147.1, 154.6 (12C, Ar)	323M⁺
3r	1561 (N⚌CH), 3379 (NH), 3464 (OH)	1.78 (p, 2H, J = 7.68 Hz, CH₂CH₂CH₂), 3.39 (t, 2H, J = 7.68 Hz, CH₂CH₂CH₂–NH), 3.81 (t, 2H, J = 7.68 Hz, N–CH₂CH₂CH₂), 4.26 (s, 1H, OH), 5.86 (s, 1H, NH), 8.01 (s, 1H, N⚌CH), 7.36–7.74 (m, 8H, Ar)	40 (CH₂CH₂CH₂), 44.7 (CH₂CH₂CH₂–N), 49.7 (N–CH₂CH₂CH₂), 151 (N⚌CH), 165.5 (CO), 114, 116, 121, 123, 125, 128.4, 132.8, 138.4, 143, 146, 147.1, 151.6 (12C, Ar)	323M⁺
3s	1567 (N⚌CH), 3381 (NH), 3468 (OH)	1.74 (p, 2H, J = 7.70 Hz, CH₂CH₂CH₂), 3.34 (t, 2H, J = 7.70 Hz, CH₂CH₂CH₂–NH), 3.76 (t, 2H, J = 7.70 Hz, N–CH₂CH₂CH₂), 4.36 (s, 1H, OH), 5.83 (s, 1H, NH), 7.97 (s, 1H, N⚌CH), 7.25–7.69 (m, 8H, Ar)	38.4 (CH₂CH₂CH₂), 43.3 (CH₂CH₂CH₂–NH), 49.1 (N–CH₂CH₂CH₂), 151.3 (N⚌CH), 164.1 (CO), 114, 116.5, 123.7, 125.7, 126.9, 130.4, 130.8, 133.5, 140.3, 145.9, 147.8, 154 (12C, Ar)	323M⁺
4a	1327 (C–N), 1730 (CO cyclic), 2908 (CH–Cl)	4.46 (d, J = 5.0 Hz, 1H, CH–Cl), 5.19 (d, J = 5.0 Hz, 1H, N–CH), 5.62 (s, 1H, NH), 6.85-7.72 (m, 9H, Ar)	54.2 (CH–Cl), 62.4 (N–CH), 159.8 (NHCO), 163.7 (CO cyclic), 117, 118.9, 121.7, 122.4, 128.4, 128.8, 129.1, 130.2, 131, 142.3, 145.9, 147.1 (12C, Ar)	384M⁺
4b	762 (C–Cl), 1338 (C–N), 1750 (C⚌O cyclic), 2910 (CH–Cl)	4.62 (d, 1H, J = 5.12 Hz, CH–Cl), 5.36 (d, 1H, J = 5.12 Hz, N–CH), 5.87 (s, 1H, NH), 6.86–7.72 (m, 8H, Ar)	53.8 (CH–Cl), 63.4 (N–CH), 166.2 (CO, cyclic), 116, 118.9, 120.7, 122.7, 125.6, 128.4, 129.8, 132.2, 135.4, 142.3, 146.9, 147.1 (12C, Ar)	418M⁺
4c	774 (C–Cl), 1333 (C–N), 1755 (CO cyclic), 2918 (CH–Cl)	4.68 (d, 1H, J = 5.10 Hz, CH–Cl), 5.36 (d, 1H, J = 5.10 Hz, N–CH), 5.84 (s, 1H, NH), 6.79–7.64 (m, 8H, Ar)	55.8 (CH–Cl), 65.1 (N–CH), 165.5 (CO cyclic), 115, 118, 120.1, 123.7, 126, 127, 128, 131, 134, 144.3, 146.1, 147.9 (12C, Ar)	418M⁺
4d	771 (C–Cl), 1333 (C–N), 1757 (CO cyclic), 2918 (CH–Cl)	4.53 (d, 1H, J = 5.10 Hz, CH–Cl), 5.26 (d, 1H, J = 5.10 Hz, N–CH), 5.92 (s, 1H, NH), 6.81–7.62 (m, 8H, Ar)	55.8 (CH–Cl), 61.4 (N–CH), 165.2 (CO cyclic), 115, 117.9, 121.7, 124.7, 126.6, 128.9, 130, 133, 135, 141.3, 145.9, 149.1 (12C, Ar)	418M⁺
4e	578 (C–Br) 1315 (C–N), 1741 (CO cyclic), 2892 (CH–Cl)	4.62 (d, 1H, J = 5.15 Hz, CH–Cl), 5.42 (d, 1H, J = 5.15 Hz, N–CH), 5.87 (s, 1H, NH), 7.35–7.95 (m, 8H, Ar)	47.1 (CH–Cl), 59.1 (N–CH), 161.3 (CO cyclic),112, 113, 117.9, 120, 122.1, 125.6, 127.4, 128.8, 135, 139, 143, 147.9 (12C, Ar)	463M⁺
4f	571 (C–Br), 1318 (C–N), 1748 (CO cyclic), 2896 (CH–Cl)	4.65 (d, 1H, J = 5.15 Hz, CH–Cl), 5.37 (d, 1H, J = 5.15 Hz, N–CH), 5.92 (s, 1H, NH), 7.31–7.92 (m, 8H, Ar)	48.7 (CH–Cl), 59.9 (N–CH), 165.3 (CO cyclic), 109, 114, 118.9, 120.7, 122.7, 125.6, 128.4, 129.8, 132.2, 139.2, 142.6, 147.1 (12C, Ar)	463M⁺
4g	565 (C–Br), 1324 (C–N), 1755 (CO cyclic), 2884 (CH–Cl)	4.64 (d, 1H, J = 5.15 Hz, CH–Cl), 5.15 (d, 1H, J = 5.15 Hz, N–CH), 5.87 (s, 1H, NH), 7.27–7.84 (m, 8H, Ar)	47.7 (CH–Cl), 58.1 (N–CH), 162.5 (CO cyclic), 111, 115.4, 118.9, 120, 121.7, 124, 127.2, 130, 131, 140, 142.1, 147.9 (12C, Ar)	463M⁺
4h	868 (C–NO), 1351 (C–N), 1538 (NO₂), 1741 (CO cyclic), 2921 (CH–Cl)	4.38 (d, 1H, J = 5.25 Hz, CH–Cl), 5.43 (d, 1H, J = 5.25 Hz, N–CH), 5.91 (s, 1H, NH), 7.1–7.71 (m, 8H, Ar)	51 (CH–Cl), 68.8 (N–CH), 161 (CO cyclic), 112, 118, 122, 124, 125, 126, 128, 132.8, 136.1, 144.3, 145.9, 147.9 (12C, Ar)	429M⁺
4i	862 (C–NO), 1357 (C–N), 1542 (NO₂), 1749 (CO cyclic), 2914 (CH–Cl)	4.39 (d, 1H, J = 5.22 Hz, CH–Cl), 5.42 (d, 1H, J = 5.22 Hz, N–CH), 5.97 (s, 1H, NH), 7.16–7.79 (m, 8H, Ar)	54 (CH–Cl), 63.8 (N–CH), 167 (CO cyclic), 115, 118.9, 122.7, 124.8, 125.9, 126.8, 128.4, 132.2, 136.9, 142.3, 146.9, 147.1 (12C, Ar)	429M⁺
4j	869 (C–NO), 1354 (C–N), 1542 (NO₂), 1745 (CO cyclic), 2918 (CH–Cl)	4.31 (d, 1H, J = 5.22 Hz, CH–Cl), 5.54 (d, 1H, J = 5.22 Hz, N–CH), 5.94 (s, 1H, NH), 7.05–7.71 (m, 8H, Ar)	54.6 (CH–Cl), 64.8 (N–CH), 163 (CO cyclic), 116.4, 117.4, 122, 123.8, 124.9, 125.2, 127.4, 130.8, 132.9, 145.7, 148.5, 151.1 (12C, Ar)	429M⁺
4k	1163 (C–O), 1326 (N–C), 1736 (CO cyclic), 2891 (CH–Cl)	3.64 (s, 3H, OCH₃), 4.41 (d, 1H, J = 5.10 Hz, CH–Cl), 5.39 (d, 1H, J = 5.10 Hz, N–CH), 5.76 (s, 1H, NH), 7.26–7.92 (m, 8H, Ar)	49.1 (CH–Cl), 54 (OCH₃), 64.4 (N–CH), 162.5 (CO cyclic), 117, 122.4, 123, 124.8, 126.9, 127, 128.7, 129, 132, 141, 148, 159 (12C, Ar)	414M⁺
4l	1168 (C–O), 1322 (N–C), 1728 (C⚌O cyclic), 2895 (CH–Cl)	3.59 (s, 3H, OCH₃), 4.49 (d, 1H, J = 5.10 Hz, CH–Cl), 5.29 (d, 1H, J = 5.10 Hz, N–CH), 5.70 (s, 1H, NH), 7.36–8.02 (m, 8H, Ar)	49.8 (CH–Cl), 54.8 (OCH₃), 62.4 (N–CH), 164.5 (CO, cyclic), 120, 123.4, 124, 125.8, 126, 127.5, 128, 129, 129.1, 145, 147, 159.6 (12C, Ar)	414M⁺
4m	1163 (C–O), 1328 (N–C), 1738 (CO cyclic), 2885 (CH–Cl)	3.52 (s, 3H, OCH₃), 4.45 (d, 1H, J = 5.12 Hz, CH–Cl),5.39 (d, 1H, J = 5.12 Hz, N–CH), 5.77 (s, 1H, NH), 7.04–7.87 (m, 8H, Ar)	47.4 (CH–Cl), 54.1 (OCH₃), 63.1 (N–CH), 163.2 (CO cyclic), 117, 119.4, 122, 124.8, 126.8, 126.5, 127, 128.4, 135.9, 147, 147.8, 157.2 (12C, Ar)	414M⁺
4n	1328 (C–N), 1740 (CO cyclic), 2889 (CH–Cl), 2924 (CH₃)	2.58 (s, 3H, CH₃), 4.53 (d, 1H, J = 5.0 Hz, CH–Cl), 5.42 (d, 1H, J = 5.0 Hz, N–CH), 5.68 (s, 1H, NH), 7.28–7.98 (m, 8H, Ar)	24.7 (CH₃), 51.7 (CH–Cl), 62.8 (N–CH), 164.8 (CO, cyclic), 117, 118.9, 120.7, 122.7, 124, 125.2, 128.3, 129.8, 132.2, 138, 146.9, 147.1 (12C, Ar)	398M⁺
4o	1322 (C–N), 1746 (CO cyclic), 2894 (CH–Cl), 2927 (CH₃)	2.56 (s, 3H, CH₃), 4.57 (d, 1H, J = 5.0 Hz, CH–Cl), 5.34 (d, 1H, J = 5.0 Hz, N–CH), 5.62 (s, 1H, NH), 7.18–7.84 (m, 8H, Ar)	23.5 (CH₃), 51 (CH–Cl), 63.8 (N–CH), 163.8 (CO, cyclic), 117.5, 118.2, 122.7, 123.3, 124.5, 125.7, 127.3, 129.1, 131.2, 136, 146.1, 147.9 (12C, Ar)	398M⁺
4p	1321 (C–N), 1746 (CO cyclic), 2876 (CH–Cl), 2913 (CH₃)	2.52 (s, 3H, CH₃),4.48 (d, 1H, J = 5.0 Hz, CH–Cl), 5.45 (d, 1H, J = 5.0 Hz, N–CH), 5.66 (s, 1H, NH), 7.21–8.09 (m, 8H, Ar)	23.4 (CH₃), 50.9 (CH–Cl), 62.2 (N–CH), 161.2 (CO cyclic), 116.4, 118.7, 120.1, 123.7, 125, 124.2, 127.3, 128.8, 132.8, 137.4, 145.4, 146.3 (12C, Ar)	398M⁺
4q	1187 (C–O), 1355 (C–N), 1758 (CO cyclic), 2917 (CH–Cl), 3467 (OH)	4.20 (s, 1H, OH), 4.59 (d, 1H, J = 5.30 Hz, CH–Cl), 5.38 (d, 1H, J = 5.30 Hz, N–CH), 5.91 (s, 1H, NH), 7.09–8.1 (m, 8H, Ar)	53.2 (CH–Cl), 63.7 (N–CH), 166.4 (CO cyclic), 113.1, 121, 122, 122.3, 123.9, 124.1, 125, 127.1, 128.2, 132, 143.2, 145.6 (12C, Ar)	400M⁺
4r	1182 (C–O), 1360 (C–N), 1762 (CO cyclic), 2923 (CH–Cl), 3469 (OH)	4.22 (s, 1H, OH), 4.57 (d, 1H, J = 5.27 Hz, CH–Cl), 5.41 (d, 1H, J = 5.27 Hz, N–CH), 5.93 (s, 1H, NH), 7.12–8.13 (m, 8H, Ar)	51.2 (CH–Cl), 64.7 (N–CH), 165.7 (CO cyclic), 113.9, 120.6, 124.2, 123.5, 124.6, 125, 125.5, 127.1, 128.7, 133, 141, 146 (12C, Ar)	400M⁺
4s	1182 (C–O), 1359 (C–N), 1752 CO cyclic), 2919 (CH–Cl), 3459 (OH)	4.25 (s, 1H, OH), 4.57 (d, 1H, J = 5.27 Hz, CH–Cl), 5.39 (d, 1H, J = 5.27 Hz, N–CH), 5.99 (s, 1H, NH), 7.19–8.21 (m, 8H, Ar)	54 (CH–Cl), 63.2 (N–CH), 165.9 (CO, cyclic), 113.5, 121.3, 122, 122.6, 123.2, 124, 125.6, 127.8, 128.5, 132.6, 144, 146.1 (12C, Ar)	400M⁺

2.2

2.2 Synthesis of compound 1

A solid supported mixture of 1,2,3-benzotriazole and 1-bromo-3-chloropropane (1:1 mole) was mixed thoroughly, taken in an open glass vessel and subjected to microwave irradiation at low power setting (25%, 200 W) for 4 min., then allowed to cool. The product was purified over column chromatography. The purified product was recrystallized from methanol at room temperature to yield compound 1.

2.3

2.3 Synthesis of compound 2

A solid supported mixture of compound 1 and urea (1:1 mole) was mixed thoroughly, taken in an open glass vessel and subjected to microwave irradiation at low power setting (25%, 200 W) for 3 min, then allowed to cool. The product was purified over column chromatography. The purified product was recrystallized from methanol at room temperature to yield compound 2.

2.4

2.4 General methods for the synthesis of compound 3(a–s)

A solid supported mixture of compound 2 and various substituted benzaldehydes (1:1 mole) was mixed thoroughly, taken in an open glass vessel and subjected to microwave irradiation at low power setting (25%, 200 W) for 2.45–4.15 min, then allowed to cool. The products were purified over column chromatography. The purified products were recrystallized from methanol at room temperature to yield compound 3(a–s).

2.5

2.5 General methods for the synthesis of compound 4(a–s)

A solid supported mixture of compound 3(a–s) and ClCH₂COCl in the presence of Et₃N (1:1:1 mole) was mixed thoroughly, taken in an open glass vessel and subjected to microwave irradiation at low power setting (25%, 200 W) for 3.10–3.45 min, then allowed to cool. The products were purified over column chromatography. The purified products were recrystallized from methanol at room temperature to yield compound 4(a–s).

3 Results and discussion

N¹-[3-{(4-substitutedaryl-3-chloro-2-oxo-azetidine)-carbamyl}-propyl]-1,2,3-benzotriazoles 4(a–s) were synthesized in four different steps. 1,2,3-benzotriazole on reaction with Cl(CH₂)₃Br at room temperature afforded N¹-(3-chloropropyl)-1,2,3-benzotriazole, compound 1. IR spectrum of compound 1 displayed absorption for (N–CH₂), (C–Cl), also indicated the disappearance of NH of 1,2,3-benzotriazole at (3442). Compound 1 on reaction with urea at room temperature yielded N¹-{3-(aminocarbamyl)-propyl}-1,2,3-benzotriazole, compound 2. IR spectrum of compound 2 showed absorption for NH and CO while absorption of (C–Cl) has been disappeared. The ¹H NMR spectrum of compound 2 displayed a signal for (CH₂–N) and its ¹³C NMR spectrum showed a signal for CO group. Compound 2 on further reaction with several selected substituted aromatic aldehydes produced N¹-{3-(substituted arylidine carbamyl)-propyl-1,2,3-benzotriazole, compound 3(a–s). Compound 3(a–s) showed the characteristic absorption for Schiff bases (N⚌CH) in IR spectra and also displayed a characteristic signal in the ¹H and ¹³C NMR spectra. In the ¹H NMR a broad signal of NH₂ has been disappeared. In the FAB–MS spectra of 3(a–s) parent ion peaks were found at the appropriate values of their molecular weights. Compound 3(a–s) on treatment with ClCH₂COCl in the presence of Et₃N furnished final products, compound 4(a–s). The ¹³C NMR spectra of compound 4(a–s) showed three signals for (N–CH), (CH–Cl) and carbonyl group of β-lactam ring and ¹H NMR spectra displayed two doublets for (N–CH) and (CH–Cl). In the IR, ¹H and ¹³C NMR spectra of compound 4(a–s) the signal for N⚌CH has been disappeared. Reaction time and the yield of the compounds are given in Table 2.

Table 2 Physical data of the compounds 1, 2, 3(a–s) and 4(a–s).

Comp.	Mol. Formula	Mol. Wt.	Melting point (°C)	Yield (%)	Time (min)	Microanalytical data
Comp.	Mol. Formula	Mol. Wt.	Melting point (°C)	Yield (%)	Time (min)	Calculated	Found
1	C₉H₁₀N₃Cl	196	78–79	78	4.00	C55.25, H5.15, N21.47	C55.21, H5.13, N21.41
2	C₁₀H₁₃N₅O	219	70–73	85	3.00	C54.73, H5.97, N31.94	C54.70, H5.92, N31.89
3a	C₁₇H₁₇N₅O	307	80–83	75	3.30	C6.43, H5.53, N22.78	C66.41, H5.50, N22.75
3b	C₁₇H₁₆N₅OCl	341	80–82	80	3.45	C59.73, H4.71, N20.48	C59.61, H4.62, N20.38
3c	C₁₇H₁₆N₅OCl	341	76–79	82	3.30	C59.73, H4.71, N20.48	C59.59, H4.66, N20.41
3d	C₁₇H₁₆N₅OCl	341	80–82	81	4.00	C59.73, H4.71, N20.48	C59.61, H4.69, N20.39
3e	C₁₇H₁₆N₅OBr	386	80–81	83	3.00	C52.86, H4.17, N18.13	C52.82, H4.13, N18.07
3f	C₁₇H₁₆N₅OBr	386	78–80	85	3.15	C52.86, H4.17, N18.13	C52.72, H4.11, N18.02
3g	C₁₇H₁₆N₅OBr	386	79–81	78	2.45	C52.86, H4.17, N18.13	C52.81, H4.03, N18.11
3h	C₁₇H₁₆N₆O₃	352	96–98	79	3.10	C57.94, H4.57, N23.85	C57.81, H4.52, N23.63
3i	C₁₇H₁₆N₆O₃	352	92–93	78	3.20	C57.94, H4.57, N23.85	C57.85, H4.54, N23.61
3j	C₁₇H₁₆N₆O₃	352	93–94	82	2.50	C57.94, H4.57, N23.85	C57.91, H4.45, N23.57
3k	C₁₈H₁₉N₅O₂	337	76–78	79	3.45	C64.08, H5.67, N20.75	C63.96, H5.56, N20.65
3l	C₁₈H₁₉N₅O₂	337	73–75	83	3.30	C64.08, H5.67, N20.75	C63.98, H5.62, N20.63
3m	C₁₈H₁₉N₅O₂	337	72–74	80	4.00	C64.08, H5.67, N20.75	C63.91, H5.57, N20.61
3n	C₁₈H₁₉N₅O	321	80–82	76	4.15	C67.27, H5.95, N21.79	C67.15, H5.90, N21.73
3o	C₁₈H₁₉N₅O	321	77–78	78	4.10	C67.27, H5.95, N21.79	C,67.11, H5.85, N,21.77
3p	C₁₈H₁₉N₅O	321	78–80	76	4.00	C67.27, H5.95, N21.79	C,67.21, H5.89, N,21.73
3q	C₁₇H₁₇N₅O₂	323	85–86	79	3.20	C63.14, H5.29, N21.65	C63.07, H5.22, N21.53
3r	C₁₇H₁₇N₅O₂	323	82–83	79	3.30	C63.14, H5.29, N21.65	C63.11, H5.18, N21.58
3s	C₁₇H₁₇N₅O₂	323	83–84	78	3.20	C63.14, H5.29, N21.65	C63.09, H5.24, N21.58
4a	C₁₉H₁₈N₅O₂Cl	384	75–76	76	3.45	C59.45, H4.72, N18.24	C59.31, H4.62, N18.13
4b	C₁₉H₁₇N₅O₂Cl₂	418	79–80	77	3.30	C54.55, H4.14, N16.74	C54.48, H4.32, N16.63.
4c	C₁₉H₁₇N₅O₂Cl₂	418	77–79	84	3.20	C54.55, H4.14, N16.74	C54.42, H4.08, N16.56%
4d	C₁₉H₁₇N₅O₂Cl₂	418	76–78	80	3.15	C54.55, H4.14, N16.74	C54.48, H4.05, N16.78
4e	C₁₉H₁₇N₅O₂BrCl	463	74–75	82	3.30	C49.31, H3.70, N15.13	C49.19, H3.64, N15.05
4f	C₁₉H₁₇N₅O₂BrCl	463	72–73	81	3.10	C49.31, H3.70, N15.13	C49.22, H3.49, N15.03%
4g	C₁₉H₁₇N₅O₂BrCl	463	79–81	79	3.45	C49.31, H3.70, N15.13	C49.25, H3.43, N15.22
4h	C₁₉H₁₇N₆O₄Cl	429	78–79	78	3.30	C53.21, H3.99, N19.59	C53.14, H3.74, N19.49
4i	C₁₉H₁₇N₆O₄Cl	429	77–78	81	3.15	C53.21, H3.99, N19.59	C53.12, H3.82, N19.53
4j	C₁₉H₁₇N₆O₄Cl	429	79–81	80	3.00	C53.21, H3.99, N19.59	C53.18, H3.92, N19.51
4k	C₂₀H₂₀N₅O₃Cl	414	77–78	81	3.20	C58.04, H4.87, N16.92	C57.94, H4.72, N16.83
4l	C₂₀H₂₀N₅O₃Cl	414	79–81	76	3.30	C58.04, H4.87, N16.92	C57.91, H4.372, N16.83
4m	C₂₀H₂₀N₅O₃Cl	414	76–78	78	3.15	C58.04, H4.87, N16.92	C57.97, H4.32, N16.88
4n	C₂₀H₂₀N₅O₂Cl	398	75–77	75	3.45	C60.37, H5.06, N7.60	C60.21, H4.92, N17.53
4o	C₂₀H₂₀N₅O₂Cl	398	73–75	76	3.30	C60.37, H5.06, N7.60	C60.25, H4.95, N17.58
4p	C₂₀H₂₀N₅O₂Cl	398	72–73	79	3.30	C60.37, H5.06, N7.60	C60.27, H4.90, N17.49
4q	C₁₉H₁₈N₅O₃Cl	400	90–91	77	3.20	C57.07, H4.53, N17.51	C56.91, H4.42, N17.43
4r	C₁₉H₁₈N₅O₃Cl	400	86–87	80	3.15	C57.07, H4.53, N17.51	C56.99, H4.30, N17.35
4s	C₁₉H₁₈N₅O₃Cl	400	88–89	81	3.30	C57.07, H4.53, N17.51	C56.91, H4.36, N17.33

4 Conclusion

In conclusion, microwave method is better for the rapid synthesis of all the above-mentioned compounds and high yield and purity were found. Reaction time and solvents use are very low.

Acknowledgements

The authors are thankful to SAIF, Indian institute of Technology New Delhi (India), and Central Drugs Research Institute, Lucknow (India), for providing spectral and analytical data of the compounds. We are also thankful to Head, Department of Chemistry, Dr. H.S. Gour, University (A Central University), Sagar, M.P. (India), for giving the facilities to carry out the work.

References

Alonsodel, E., Pozo, C., Gonzalez, J., 2002. Synlett., 69.
Annapukowska D., Bartulewiczand K., Midura-Nowaczek, . Acta Poloniae Pharm.-Drug Res.. 2006;62:59.
Asati K.C., Srivastava S.K., Srivastava S.D., . Indian J. Chem.. 2006;45B:526.
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Introduction

Materials and methods

Experimental
Synthesis of compound 1
Synthesis of compound 2
General methods for the synthesis of compound 3(a–s)
General methods for the synthesis of compound 4(a–s)

Results and discussion

Conclusion

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[1] Alonsodel, E., Pozo, C., Gonzalez, J., 2002. Synlett., 69.

[2] Annapukowska D., Bartulewiczand K., Midura-Nowaczek, . Acta Poloniae Pharm.-Drug Res.. 2006;62:59.

[3] Asati K.C., Srivastava S.K., Srivastava S.D., . Indian J. Chem.. 2006;45B:526.

[4] Caliendo G., Di Carlo R., Greco G., Meli R., Novellino E., Perissutt E., Santagada V., . Eur. J. Med. Chem.. 1995;30:77.

[5] Chavan A.A., Pai N.R., . Molecules. 2007;12:2467.

[6] Lebouvier N., Pagnies F., Duflos M., Pape P.Le, Young Na. Min, Guillaume B.L., Borgne M.L., . Bioorg. Med. Chem. Lett.. 2006;17:3686.

[7] Mulwad V.V., Mir Abid Ali, . J. Kor. Chem. Soc.. 2008;52(6):649.

[8] Nema A., Srivastava S.K., . J. Indian Chem. Soc.. 2007;84:1037.

[9] Parikh K.A., Oza P.S., Parikh A.R., . Indian J. Chem.. 2000;39B:716.

[10] Parikh A.K., Oza P.S., Bhatt S.B., . Indian J. Chem.. 2005;44B:585.

[11] Patel R.B., Desai P.S., Chikhalia K.H., . Indian J. Chem.. 2006;45B:773.

[12] Rawat T.R., Srivastava S.D., . Indian J. Chem.. 1998;37B:91.

[13] Sanna P., Carta A., Nikookar M.E., . Eur. J. Med. Chem.. 2000;35(5):535.

[14] Shukla D.K., Srivastava S.D., . Indian J. Chem.. 2008;47B:463.

[15] Singh G.S., . Mini-Rev. Med. Chem.. 2004;4:93.

[16] Singh G.S., Mbukwa Elbert, Pheko Tshepo, . Arkivoc. 2007;9:80.

[17] Skiles J.W., McNeil D., . Tetrahedron Lett.. 1990;31:7277.

[18] Srivastava S.K., Srivastava S.L., Srivastava S.D., . Indian J. Chem.. 1999;39B:183.

[19] Srivastava S.K., Srivastava S., Srivastava S.D., . Indian J. Chem.. 2000;38B:464.

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Facile synthesis of new 1,2,3-benzotriazolo-2-oxo-azetidine analogues by microwave irradiation

Abstract

Keywords

Microwave synthesis of 1,2,3-benzotriazole

Azetidinone

1 Introduction

2 Materials and methods

2.1 Experimental

2.2 Synthesis of compound 1

2.3 Synthesis of compound 2

2.4 General methods for the synthesis of compound 3(a–s)

2.5 General methods for the synthesis of compound 4(a–s)

3 Results and discussion

4 Conclusion

Acknowledgements

References

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