A Simple One-Pot Synthesis of 2-Substituted Quinazolin-4(3H)-ones from 2-Nitrobenzamides by Using Sodium Dithionite

Angel H. Romero; José Salazar; Simón E. López

doi:10.1055/s-0033-1338854

Synthesis, Table of Contents

Synthesis 2013; 45(14): 2043-2050
DOI: 10.1055/s-0033-1338854

paper

A Simple One-Pot Synthesis of 2-Substituted Quinazolin-4(3H)-ones from 2-Nitrobenzamides by Using Sodium Dithionite

Authors

Angel H. Romero

Laboratorio de Química Medicinal y Heterociclos, Departamento de Química, Edificio de Química y Procesos, Universidad Simón Bolívar, Valle de Sartenejas, Apartado 89000, Baruta, Caracas 1080-A, Venezuela Fax: +58(212)9063961 Email: slopez@usb.ve
José Salazar

Laboratorio de Química Medicinal y Heterociclos, Departamento de Química, Edificio de Química y Procesos, Universidad Simón Bolívar, Valle de Sartenejas, Apartado 89000, Baruta, Caracas 1080-A, Venezuela Fax: +58(212)9063961 Email: slopez@usb.ve
Simón E. López*

Laboratorio de Química Medicinal y Heterociclos, Departamento de Química, Edificio de Química y Procesos, Universidad Simón Bolívar, Valle de Sartenejas, Apartado 89000, Baruta, Caracas 1080-A, Venezuela Fax: +58(212)9063961 Email: slopez@usb.ve

Abstract

All articles of this category

Abstract

A simple one-pot procedure for the preparation of 2-(het)arylquinazolin-4(3H)-ones starting from readily available 2-nitrobenzamides and (het)aryl aldehydes is described. Sodium dithionite is used as the reducing agent for the nitro group, and its decomposition in situ in aqueous N,N-dimethylformamide leads to the final oxidation step that gives the desired heterocyclic compounds.

Key words

heterocycles - oxidations - dehydrogenations - reductions - amides - aldehydes

Full Text

References

References

1a Rewcastle GW In Comprehensive Heterocyclic Chemistry III . Vol. 8. Katritzky AR, Ramsden CA, Scriven EF. V, Taylor RJ. K. Elsevier; Oxford: 2008. Chap. 2, 11
1b Undheim K, Benneche T In Comprehensive Heterocyclic Chemistry II . Vol. 6. Katritzky AR, Rees CW, Scriven EV. F. Pergamon; Oxford: 1996. Chap. 2, 9

2 Ozaki K, Yamada Y, Oine T, Ishizuka T, Iwasawa Y. J. Med. Chem. 1985; 28: 568
3 Cao SL, Feng YP, Jiang YY, Liu SY, Ding GY, Li RT. Bioorg. Med. Chem. Lett. 2005; 15: 1915
4 Wolfe JF, Rathman TL, Sleevi MC, Campbell JA, Greenwood TD. J. Med. Chem. 1990; 33: 161

5a Hussain MA, Chiu AT, Price WA, Timmermans PB, Shefter E. Pharm. Res. 1988; 5: 242
5b Hess HJ, Cronin TH, Scriabine A. J. Med. Chem. 1968; 11: 130

6 Terashima K, Shimamura H, Kawase A, Tanaka Y, Tanimura T, Kamisaki T, Ishizuka Y, Sato M. Chem. Pharm. Bull. 1995; 43: 2021
7 Kurogi Y, Inoue Y, Tsutsumi K, Nakamura S, Nagao K, Yohsitsugu H, Tsuda Y. J. Med. Chem. 1996; 39: 1433
8 Jiang S, Zeng Q, Gettayacamin M, Tungtaeng A, Wannaying S, Lim A, Hansukjariya P, Okunji CO, Zhu S, Fang D. Antimicrob. Agents Chemother. 2005; 49: 1169
9 Kunes J, Bazant J, Pour M, Waisser K, Slosárek M, Janota J. Farmaco 2000; 55: 725

10a Witt A, Bergman J. Curr. Org. Chem. 2003; 7: 659
10b Mitscher LA, Wong WC, De Meulenere T, Sulko J, Drake S. Heterocycles 1981; 15: 1017

11a Amin AH, Mehta DR. Nature (London) 1959; 184: 1317
11b Chatterjee A, Ganguly M. Phytochemistry 1968; 7: 307
11c Joshi BS, Newton MG, Lee DW, Barber AD, Pelletier SW. Tetrahedron: Asymmetry 1996; 7: 25
11d Ghosal S, Chauhan PS. R. B, Mehta R. Phytochemistry 1975; 14: 830

12a Jang CS, Fu FY, Wang CY, Huang KC, Lu G, Thou TC. Science 1946; 103: 59
12b Koepfli JB, Mead JF, Brockman JA. Jr. J. Am. Chem. Soc. 1947; 69: 1837

13 Kobayashi S, Ueno M, Suzuki R, Ishitani H. Tetrahedron Lett. 1999; 40: 2175
14 Connolly DJ, Guiry PJ. Synlett 2001; 1707
15 Majo VJ, Perumal PT. Tetrahedron Lett. 1996; 37: 5015
16 Liu J.-F, Lee J, Dalton AM, Bi G, Yu L, Baldino CM, McElory E, Brown M. Tetrahedron Lett. 2005; 46: 1241
17 Abdel-Jalil RJ, Voelter W, Saeed M. Tetrahedron Lett. 2004; 45: 3475
18 Ighilahriz K, Boutemeur B, Chami F, Rabia C, Hamdi M, Hamdi SM. Molecules 2008; 13: 779
19 Liu X, Fu H, Jiang Y, Zhao Y. Angew. Chem. Int. Ed. 2009; 48: 348
20 Yang D, Fu H, Hu L, Jiang Y, Zhao Y. J. Comb. Chem. 2009; 11: 653
21 Errede LA, McBrady JJ, Oien HT. J. Org. Chem. 1977; 42: 656
22 Snider BB, Zeng H. Heterocycles 2003; 61: 173
23 Salehi P, Dabiri M, Zolfigol MA, Baghbanzadeh M. Tetrahedron Lett. 2005; 46: 7051

24a Imai Y, Sato S, Takasawa R, Ueda M. Synthesis 1981; 35
24b López SE, Rosales ME, Urdaneta N, Godoy MV, Charris JE. J. Chem. Res., Synop. 2000; 258

25 Wang G.-W, Miao C.-B, Kang H. Bull. Chem. Soc. Jpn. 2006; 79: 1426
26 Heravi MM, Tavakoli-Hoseini N, Bamoharram FF. Synth. Commun. 2011; 41: 707
27 Giri R, Lam JK, Yu JQ. J. Am. Chem. Soc. 2010; 132: 686
28 Zheng Z, Alper H. Org. Lett. 2008; 10: 829
29 Zhou J, Fu L, Lv M, Liu J, Pei D, Ding K. Synthesis 2008; 3974
30 Xu W, Jin Y, Liu H, Jiang Y, Fu H. Org. Lett. 2011; 13: 1274

31a Khurana JK, Kukreja G. J. Heterocycl. Chem. 2003; 40: 677
31b Rao VB, Ratnam CV. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1979; 18: 409
31c Yoo CL, Fettinger JC, Kurth MJ. J. Org. Chem. 2005; 70: 6941
31d Moore JA, Sutherland GJ, Sowerby R, Kelly EG, Palermo S, Webster W. J. Org. Chem. 1969; 34: 887
31e Yale HL. J. Heterocycl. Chem. 1977; 14: 1357
31f Böhme H, Böing H. Arch. Pharm. (Weinheim, Ger.) 1960; 293: 1011
31g Cai G, Xu X, Li Z, Weber WP, Lu P. J. Heterocycl. Chem. 2002; 39: 1271
31h Shi D, Rong L, Wang J, Zhuang Q, Wang X, Hu H. Tetrahedron Lett. 2003; 44: 3199
31i Chen JX, Wu HY, Su WK. Chin. Chem. Lett. 2007; 18: 536
31j Shaabani A, Maleki A, Mofakham H. Synth. Commun. 2008; 38: 3751
31k Salehi P, Dabiri M, Zolfigol MA, Baghbanzadeh M. Synlett 2005; 1155
31l Dabiri M, Salehi P, Otokesh S, Baghbanzadeh M, Kozehgary G, Mohammadi AA. Tetrahedron Lett. 2005; 46: 6123
31m Gao L, Ji H, Rong L, Tang D, Zha Y, Shi Y, Tu S. J. Heterocycl. Chem. 2011; 48: 957
31n Su W, Yang B. Aust. J. Chem. 2002; 55: 695
31o Bunce RA, Nammalwar B. J. Heterocycl. Chem. 2011; 48: 991

32a Balasubramanian M, Keay JG In e-EROS Encyclopedia of Reagents for Organic Synthesis. Paquette LA. Wiley; New York: 2010–2013,
32b Makarov SV, Silaghi-Dumitrescu R. J. Sulfur Chem. 2012;

33a Yang D, Fokas D, Li J, Yu L, Baldino CM. Synthesis 2005; 47
33b Surpur MP, Singh PR, Patil SB, Samant SD. Synth. Commun. 2007; 37: 1375

34 Oda S, Shimizu H, Aoyama Y, Ueki T, Shimizu S, Osato H, Takeuchi Y. Org. Process Res. Dev. 2012; 16: 96
35 De Vries JG, Kellogg RM. J. Org. Chem. 1980; 45: 4126
36 Hour MJ, Huang LJ, Kuo SC, Xia Y, Bastow K, Nakanishi Y, Hamel E, Lee KH. J. Med. Chem. 2000; 43: 4479

37a Heravi MM, Montazeri N, Rahimizadeh M, Bakavoli M, Ghassemzadeh M. Pol. J. Chem. 2004; 78: 2101
37b Zhou J, Fang J. J. Org. Chem. 2011; 76: 7730
37c Chen J, Wu D, He F, Liu M, Wu H, Ding J, Su W. Tetrahedron Lett. 2008; 49: 3814
37d Petridou-Fischer J, Papadopoulos EP. J. Heterocycl. Chem. 1983; 20: 1159
37e Wang X.-S, Yang K, Zhang M.-M, Yao C.-S. Synth. Commun. 2010; 40: 2633
37f Bhat BA, Sahu DP. Synth. Commun. 2004; 34: 2169
37g Mohamed MM, El-Khamry AA, El-Nagdy S, Shoshaa SW. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1986; 25: 207
37h Rostamizadeh S, Amani AM, Aryan R, Ghaieni HR, Shadjou N. Synth. Commun. 2008; 38: 3567

38 International Programme on Chemical Safety, INCHEM database. http://www.inchem.org/documents/sids/sids/7775146.pdf (accessed Jan. 2013).
39 Ghosh P, O’Driscoll KF. J. Polym. Sci., Part B: Polym. Lett. 1966; 4: 519
40 López SE, Restrepo J, Pérez B, Ortiz S, Salazar J. Bull. Korean Chem. Soc. 2009; 30: 1628
41 Restrepo J, Salazar J, López SE. Phosphorus, Sulfur Silicon Relat. Elem. 2011; 186: 2311

Supplementary Material

Supporting Information (PDF) (opens in new window)