Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2015; 47(07): 949-954
DOI: 10.1055/s-0034-1380111
DOI: 10.1055/s-0034-1380111
paper
Cooperation of a Reductant and an Oxidant in One Pot To Synthesize Amides from Nitroarenes and Aldehydes
Further Information
Publication History
Received: 04 November 2014
Accepted after revision: 19 December 2014
Publication Date:
10 February 2015 (online)
Abstract
The reductant zinc powder and the oxidant sodium chlorate were used together in an appropriate ratio in one pot under ambient conditions, to provide an environmentally friendly, effective, and convenient method for the synthesis of aromatic amides in good yields from nitroarenes and aldehydes in the green solvents alcohol and water under atmospheric conditions. The good results indicate that reductants and oxidants with opposing properties can not only be used together without any adverse effects, but also improve the reaction yield through their cooperation.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380111.
- Supporting Information
-
References
- 1 Pattabiraman VR, Bode JW. Nature (London) 2011; 480: 471
- 2 Li GL, Kung KK, Wong MK. Chem. Commun. 2012; 48: 4112
- 3 Zhu J, Zhang Y, Shi F, Deng Y. Tetrahedron Lett. 2012; 53: 3178
-
4 Ghosh SC, Muthaiah S, Zhang Y, Xu X, Hong SH. Adv. Synth. Catal. 2009; 351: 2643
- 5 Nordstroem LU, Vogt H, Madsen R. J. Am. Chem. Soc. 2008; 130: 17672
-
6 Muthaiah S, Ghosh SC, Jee JE, Chen C, Zhang J, Hong SH. J. Org. Chem. 2010; 75: 3002
- 7 Naota T, Murahashi SI. Synlett 1991; 693
- 8 Pookot SK, Kuriya M. Chem. Pap. 2012; 66: 772
- 9 Bellamy FD, Ou K. Tetrahedron Lett. 1984; 25: 839
- 10 Kijima M, Nambu Y, Endo T. J. Org. Chem. 1984; 49: 1434
- 11 Ge G, Tao Y, Jing J. Green Chem. 2008; 10: 439
- 12 Li M, Hu L, Cao XQ, Hong HY, Lu JM, Gu HW. Chem. Eur. J. 2011; 17: 2763
- 13 Bhattacharya A, Suarez V, Tamez VJr, Wu JJ. Tetrahedron Lett. 2006; 47: 3221
- 14 Li G, Wang XW, Tian C, Zhang TB, Zhang ZL, Liu JY. Tetrahedron Lett. 2012; 53: 5193
- 15 Jain SK, Kumar KA. A, Bharate SB, Vishwakarma RA. Org. Biomol. Chem. 2014; 12: 6465
-
16 Wahba AE, Peng JN, Hamann MT. Tetrahedron Lett. 2009; 50: 3901
- 17 Liang J, Jing LJ, Shang Z. Tetrahedron 2011; 67: 8532
- 18 Ekoue-Kovi K, Wolf C. Org. Lett. 2007; 9: 3429
- 19 Chang JW, Ton TM, Tania S, Taylor PC, Chan PW. Chem. Commun. 2010; 46: 922
- 20 Tamaru Y, Yamada Y, Yoshida Z. Synthesis 1983; 474
- 21 Takashi T, Atsuki Y, Toshiyasu M. Org. Process Res. Dev. 2005; 9: 593
- 22 Deadman BJ, Hopkin MD, Baxendale IR, Ley SV. Org. Biomol. Chem. 2013; 11: 1766
- 23 Lee CK, Yu JS, Ji YR. J. Heterocycl. Chem. 2002; 39: 1219
- 24 Fahmy AF. M, Sayed GH, Hamed AA, Morsy AA. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1978; 16: 869
- 25 Fukui K, Kitano H, Osaka T, Inamoto Y, Shirai H. Nippon Kagaku Zasshi 1958; 79: 1428
- 26 Zhu ZW, Shi L, Ruan XM, Yang Y, Li HQ, Xu SP, Zhu HL. J. Enzyme Inhib. Med. Chem. 2011; 26: 37
- 27 Tetjuewa LA, Petjunin PA. Zh. Obshch. Khim. 1958; 28: 739
- 28 Wawzonek S, Paschke EE. J. Org. Chem. 1971; 36: 1474
- 29 Tang XR, Chen SL, Wang L. Asian J. Chem. 2012; 24: 2516
- 30 Das VK, Thakur AJ, Devi RR. Appl. Catal. A: Gen. 2013; 456: 118
- 31 Chiriac CI. Rev. Roum. Chim. 1979; 24: 609
- 32 Taborsky RG, Darker GD, Kaye S. J. Am. Pharm. Assoc. 1959; 48: 503
- 33 Chattaway FD. J. Chem. Soc. 1904; 85, 386
- 34 Hsi RS. P. (Upjohn Co.) US Patent 3288844, 1966
- 35 Manimaran T, Thiruvengadam TK, Ramakrishnan VT. Synthesis 1975; 739
- 36 Coppola GM, Damon RE, Kukkola PJ, Stanton JL. (Novartis AG, Novartis Pharma Gmbh) WO 2004065351, 2004
- 37 Bain DI, Smalley RK. J. Chem. Soc. C 1968; 1593
- 38 Sveinbjornsson A, VanderWerf CA. J. Am. Chem. Soc. 1951; 73: 869
- 39 Shepard AF, Winslow NR, Johnson JR. J. Am. Chem. Soc 1930; 52: 2083
- 40 Tsuchiya C. Nippon Kagaku Zasshi 1961; 82: 1395