An Efficient One-Pot Strategy for the Synthesis of Triazole-Fused 1,4-Benzodiazepinones from N-Substituted 2-Azidobenzamides

K. C. Majumdar; Sintu Ganai

doi:10.1055/s-0033-1339346

Synthesis, Table of Contents

Synthesis 2013; 45(18): 2619-2625
DOI: 10.1055/s-0033-1339346

paper

An Efficient One-Pot Strategy for the Synthesis of Triazole-Fused 1,4-Benzodiazepinones from N-Substituted 2-Azidobenzamides

K. C. Majumdar*

Department of Chemistry, University of Kalyani, Kalyani 741235, West Bengal, India Fax: +91(33)25828282 Email: kcm@klyuniv.ac.in

,

Sintu Ganai

Department of Chemistry, University of Kalyani, Kalyani 741235, West Bengal, India Fax: +91(33)25828282 Email: kcm@klyuniv.ac.in

› Author Affiliations

Abstract

All articles of this category

Abstract

A catalyst-free, one-pot strategy for the synthesis of 1,2,3-triazole-fused 1,4-benzodiazepinone derivatives from N-substituted 2-azidobenzamides and propargyl bromide, in the presence of a base, is reported. The products are formed in good to excellent yields via N-alkylation followed by a 1,3-dipolar cycloaddition.

Key words

fused triazole - azide–alkyne cycloaddition - 1,4-benzodiazepinones - N-substituted 2-azidobenzamides - catalyst-free

Full Text

References

References

1a Majumdar KC, Ganai S. Synlett 2011; 1881
1b Spencer J, Rathnam RP, Motukuri M, Kotha AK, Richardson SC. W, Hazrati A, Hartley JA, Malec L, Hursthouse MB. Dalton Trans. 2009; 4299
1c Meanwell NA, Walker MA. 1,4-Diazepines . In Comprehensive Heterocyclic Chemistry III . Vol. 13. Katritzky AR, Ramsden CA, Taylor RJ. K. Elsevier; Oxford: 2008. Chap. 13.06
1d Gribble MW, Ellman JA, Bergman RG. Organometallics 2008; 27: 2152
1e Laustsen LS, Sams CK. J. Comb. Chem. 2007; 9: 1094
1f Carlier PR, Zhao H, MacQuarrie-Hunter SL, DeGuzman JC, Hsu DC. J. Am. Chem. Soc. 2006; 128: 15215
1g Grunewald GL, Dahanukar VH, Ching P, Criscione KR. J. Med. Chem. 1996; 39: 3539
1h Evans BE, Rittle KE, Bock MG, Dipardo RM, Freidinger RM, Whitter WL, Lundell GF, Veber DF, Anderson PS, Chang RS. L, Lotti VJ, Cerino DJ, Chen TB, Kling PJ, Kunkel KA, Springer JP, Hirshfield J. J. Med. Chem. 1988; 31: 2235

2a Baldessarini RJ In The Pharmacologic Basis of Therapeutics . Vol. 1. Gilman AG, Goodman LS, Ralland TW, Murad F. Macmillan; New York: 1985: 391
2b Landquist JK In Comprehensive Heterocyclic Chemistry . Vol. 1. Katritzky AR, Rees CW. Pergamon; Oxford: 1984. Chap. 1.06
2c Sharp JT In Comprehensive Heterocyclic Chemistry . Vol. 7. Katritzky AR, Rees CW. Pergamon; Oxford: 1984. Chap. 5.18
2d Vida JA In Medicinal Chemistry . Wolf MV, Burger A. Wiley; New York: 1981. Part III

3a Majumdar KC, Ray K, Ganai S, Ghosh T. Synthesis 2010; 858
3b Thomas AW. Bioorg. Med. Chem. Lett. 2002; 12: 1881

4a Roger-Evans M, Spurr P, Hennig M. Tetrahedron Lett. 2003; 44: 2425
4b Broggini G, Orlandi M, Turconi A, Zoni C. Org. Prep. Proced. Int. 2003; 35: 609
4c Broggini G, Molteni G, Terraneo A, Zecchi G. Tetrahedron 1999; 55: 14803
4d Gu Z.-Q, Wong G, Dominguez C, de Costa BR, Rice KC, Skolnick P. J. Med. Chem. 1993; 36: 1001

5 Ogawa K, Matsushita Y. Chem. Pharm. Bull. 1992; 40: 2442

6a Alajarín M, Cabrera J, Pastor A, Villalgordo JM. Tetrahedron Lett. 2007; 48: 3495
6b Scharf MB, Roth PB, Dominguez RA, Ware JC. J. Clin. Pharmacol. 1990; 30: 461

7 Donohue AR, Dannals RF. Tetrahedron Lett. 2009; 50: 7271

8a Basolo L, Beccalli EM, Borsini E, Gianluigi Broggini G, Maisaa Khansaa M, Rigamonti M. Eur. J. Org. Chem. 2010; 1694
8b Patel N, Chambers CS, Hemming K. Synlett 2009; 3043
8c Broggini G, Marchi ID, Martinelli M, Paladino G, Pilati T, Terraneo A. Synthesis 2005; 2246
8d Hunkeler W. Chimia 1993; 47: 141

9a Sahoo S, Veliyath SK, Mahendra Kumar CB. Int. J. Res. Pharm. Sci. 2012; 3: 326
9b Majumdar KC, Ray K. Synthesis 2011; 3767
9c Genin MJ, Allwine DA, Anderson DJ, Barbachyn MR, Emmert DE, Garmon SA, Graber DR, Grege KC, Hester JB, Hutchinson DK, Morris J, Reischer RJ, Ford CW, Zurenko GE, Hamel JC, Schaadt RD, Stapert D, Yagi BH. J. Med. Chem. 2000; 43: 953
9d Palhagen S, Canger R, Henriksen O, van Parys JA, Riviere M.-E, Karolchyk MA. Epilepsy Res. 2001; 43: 115
9e Velázquez S, Alvarez R, Pérez C, Gago F, De Clercq E, Balzarini J, Camarasa MJ. Antiviral Chem. Chemother. 1998; 9: 481
9f Fung-Tomc JC, Huczko E, Minassian B, Bonner DP. Antimicrob. Agents Chemother. 1998; 42: 313
9g Fan W.-Q, Katritzky AR In Comprehensive Heterocyclic Chemistry II . Vol. 4. Katritzky AR, Rees CW, Scriven EF. V. Elsevier; Oxford: 1996: 1-26
9h Alvarez R, Velásquez S, San-Félix A, Aquaro S, De Clercq E, Perno C.-F, Karlsson A, Balzarini J, Camarasa MJ. J. Med. Chem. 1994; 37: 4185

10a Huisgen R. Pure Appl. Chem. 1989; 61: 613
10b Huisgen R. 1,3-Dipolar Cycloaddition Chemistry . Wiley; New York: 1984: 1-176
10c Huisgen R, Szeimies G, Moebius L. Chem. Ber. 1967; 100: 2494

11a Donnelly KF, Petronilho A, Albrecht M. Chem. Commun. 2013; 49: 1145
11b Sobenina LN, Tomilin DN, Ushakov IA, Mikhaleva AI, Ma JSh, Yang G, Trofimov BA. Synthesis 2013; 45: 678
11c Sudhir VS, Nasir Bag RB, Chandrasekaran S. Eur. J. Org. Chem. 2008; 2423
11d Pokorski JK, Millers Jenkins LM, Feng H, Durell SR, Bai Y, Appella DH. Org. Lett. 2007; 9: 2381
11e Kumar I, Rode CV. Chem. Lett. 2007; 36: 592
11f Mahapatra DK, Maity PK, Gonnade RG, Chorgade MS, Gurgar MK. Synlett 2007; 1893
11g Couty F, Durrat F, Prim D. Tetrahedron Lett. 2004; 45: 3725

12a Hooyberghs G, De Coster H, Vachhani DD, Ermolat’ev DS, Van der Eycken EV. Tetrahedron 2013; 69: 4331
12b Wang XL, Zheng XF, Liu RH, Reiner J, Chang JB. Tetrahedron 2007; 63: 3389
12c Beccalli EM, Broggini G, Paladino G, Pilati T, Pontremoli G. Tetrahedron: Asymmetry 2004; 15: 687
12d Matthews JM, Dyatkin AB, Evangelisto M, Gauthier DA, Hecker LR, Hoekstra WJ, Liu F, Poulter B, Sorgi KL, Maryanoff BE. Tetrahedron: Asymmetry 2004; 15: 1259
12e Hemming K, Loukou C. Tetrahedron 2004; 60: 3349
12f Correa A, Herrero MT, Tellitu I, Dominguez E, Moreno I, SanMartin R. Tetrahedron 2003; 59: 7103
12g Herrero S, Garcìa-Lopez MT, Herranz R. J. Org. Chem. 2003; 68: 4582
12h Surman MD, Mulvihill MJ, Miller MJ. Org. Lett. 2002; 4: 139
12i Abrous L, Hynes Jr J, Friederich SR, Smith III AB, Hirschmann R. Org. Lett. 2001; 3: 1089
12j Broggini G, Molteni G, Zecchi G. Synthesis 1995; 647
12k Wang T, Lui AS, Cloudsdale IS. Org. Lett. 1999; 1: 1835
12l Ammadi F, Boukhris S, Souizi A, Coudert G. Tetrahedron Lett. 1999; 40: 6517
12m Sugimori T, Okawa T, Eguchi S, Kakehi A, Yashima E, Okamoto Y. Tetrahedron 1998; 54: 7997

13 Akritopoulou-Zanze I, Gracias V, Djuric SW. Tetrahedron Lett. 2004; 45: 8439
14 Chambers CS, Patel N, Hemming K. Tetrahedron Lett. 2010; 51: 4859
15 Chowdhury C, Sasmal AK, Achari B. Org. Biomol. Chem. 2010; 8: 4971
16 Lemrova B, Soural M. ACS Comb. Sci. 2012; 14: 645
17 Jiang B, Li Q.-Y, Zhang H, Tu S.-J, Pindi S, Li G. Org. Lett. 2012; 14: 700
18 Vachhani DD, Kumar A, Modha SG, Sharma SK, Parmar VS, Van der Eycken EV. Eur. J. Org. Chem. 2013; 1223

For earlier examples of the syntheses of heterocycles from our group, see:

19a Majumdar KC, Ganai S. Beilstein J. Org. Chem. 2013; 9: 503
19b Majumdar KC, Ganai S, Sinha B. Tetrahedron 2012; 68: 7806
19c Majumdar KC, Ganai S, Nandi RK, Ray K. Tetrahedron Lett. 2012; 53: 1553
19d Majumdar KC, Ganai S, Nandi RK. New J. Chem. 2011; 35: 1355
19e Majumdar KC, Ganai S, Chattopadhyay B, Ray K. Synlett 2011; 2369
19f Majumdar KC, Nandi RK, Ganai S, Taher A. Synlett 2011; 116
19g Majumdar KC, Ray K, Ganai S. Synthesis 2010; 2101

Supplementary Material

Supporting Information