An efficient and one-pot reductive cyclization for synthesis of 2-substituted benzimidazoles from o-nitroaniline under microwave conditions

Hossein Naeimi; Nasrin Alishahi

Journal of Industrial and Engineering Chemistry, Vol.20, No.4, 2543-2547, July, 2014

DOI10.1016/j.jiec.2013.10.038 Export Citation

An efficient and one-pot reductive cyclization for synthesis of 2-substituted benzimidazoles from o-nitroaniline under microwave conditions

Hossein Naeimi^†, and Nasrin Alishahi

Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan 87317, Islamic Republic of Iran

E-mail:

A versatile and high yielding procedure for the direct generation of 2-substituted benzimidazoles from onitroaniline and aryl aldehydes in the presence of sodium dithionite as reducing agent under microwave irradiation is described. The obtained products were confirmed by physical and spectroscopic data such as IR, 1H NMR and 13C NMR. This procedure has a lot of advantages including; excellent yields of products, short reaction times, mild reaction conditions, easy work-up and other noteworthy advantages which make this method a valid contribution to the existing methodologies.

Keywords:O-nitroaniline;Synthesis;Benzimidazoles;Aryl aldehydes;Sodium dithionite

[References]

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Porcari AR, Devivar RV, Kucera LS, Drach JC, Townsend LB, J. Med. Chem., 41, 1251 (1998)
Roth M, Morningstar ML, Boyer PL, Hughes SH, Buckheit RW, Michejda CJ, J. Med. Chem., 40, 4199 (1997)
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Yoshiyuki T, Kazuaki Y, Hokkaido Daigaku Koagakubu Kenkyu Hokoku Chem. Abstr. 93 (1980), 45-49204537k.
Pushkina LN, Mazalov SA, Poatovskii I Obshch Khim. 32 (1962) 2624, Chem. Abstr. 58 (1963) 9049h.
Kumar R, Joshi YC, Eur. J. Chem., 4, 606 (2007)
Kappe CO, Dallinger D, Murphree SS, Practical Microwave Synthesis for Organic Chemists, Wiley-VCH, Weinheim, 2009, pp. 21-22.
Kodomari M, Tamaru Y, Aoyama T, Synth. Commun., 3029 (2004)
Romero AH, Salazar J, Lopez SE, Synthesis, 45, 2043 (2013)
Nagawade RR, Shinde DB, Chin. Chem. Lett., 17, 453 (2006)
Xiangming H, Huiqiang M, Yulu W, Arkivoc, 150 (2007)
Nagawade R, Shinde DB, Indian J. Chem., 46, 349 (2007)
Naeimi H, Alishahi N, J. Chin. Chem. Soc., 59, 1001 (2012)
Naeimi H, Alishahi N, J. Chem. Res., 208 (2013)
Naeimi H, Alishahi N, J. Exp. Nanosci., http://dx.doi.org/10.1080/17458080.2013.822575 (2013)
Navarrete-Vazquez G, Moreno-Diaz H, Aguirre-Crespo F, Leon-Rivera I, Villalobos-Molina R, Munoz-Munizd O, Estrada-Sotoa S, Bioorg. Med. Chem. Lett., 16, 4169 (2006)
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Rostamizadeh S, Aryan R, Ghaieni HR, Amani AM, J. Heterocycl. Chem., 46, 74 (2009)

[1] Grimmett MR, in: Katrizky AR, Rees CW, Scriven EFV (Eds.), Comprehensive Heterocyclic Chemistry, vol. 3, Pergamon, Oxford, 1996, pp. 77-220.

[2] Tamm I, Science, 126, 1235 (1957)

[3] Porcari AR, Devivar RV, Kucera LS, Drach JC, Townsend LB, J. Med. Chem., 41, 1251 (1998)

[4] Roth M, Morningstar ML, Boyer PL, Hughes SH, Buckheit RW, Michejda CJ, J. Med. Chem., 40, 4199 (1997)

[5] Kohara Y, Kubo K, Imamiya E, Wada T, Inada Y, Naka T, J. Med. Chem., 39, 5228 (1996)

[6] Kim JS, Gatto B, Yu C, Liu A, Liu LF, LaVoie EJ, J. Med. Chem., 39, 992 (1996)

[7] Elokdah HM, Chai SY, Sulkowski TS, 1998 US Patent 5 764 473 (1998). Chem. Abstr. 129 58 784g.

[8] Zarrinmaye H, Zimmerman DM, Cantrell BE, Schober DA, Bruns RE, Gackenheimer SL, Ornstein PL, Hipskind PA, Britton TC, Gehlert D, Bioorg. Med. Chem. Lett., 9, 647 (1999)

[9] Lewis JC, Wiedemann SH, Bergman RG, Ellman JA, J. Org. Lett., 6, 35 (2004)

[10] Sharghi H, Asemani OR, Synth. Commun., 38, 1128 (2008)

[11] Paul S, Basu B, Tetrahedron Lett., 53, 4130 (2012)

[12] Perston PN, in: Weissberger A, Taylor EC (Eds.), Benzimidazoles and Congeneric Tricyclic, vol. 2, 2012, p. 1122.

[13] Yoshiyuki T, Kazuaki Y, Hokkaido Daigaku Koagakubu Kenkyu Hokoku Chem. Abstr. 93 (1980), 45-49204537k.

[14] Pushkina LN, Mazalov SA, Poatovskii I Obshch Khim. 32 (1962) 2624, Chem. Abstr. 58 (1963) 9049h.

[15] Kumar R, Joshi YC, Eur. J. Chem., 4, 606 (2007)

[16] Kappe CO, Dallinger D, Murphree SS, Practical Microwave Synthesis for Organic Chemists, Wiley-VCH, Weinheim, 2009, pp. 21-22.

[17] Kodomari M, Tamaru Y, Aoyama T, Synth. Commun., 3029 (2004)

[18] Romero AH, Salazar J, Lopez SE, Synthesis, 45, 2043 (2013)

[19] Nagawade RR, Shinde DB, Chin. Chem. Lett., 17, 453 (2006)

[20] Xiangming H, Huiqiang M, Yulu W, Arkivoc, 150 (2007)

[21] Nagawade R, Shinde DB, Indian J. Chem., 46, 349 (2007)

[22] Naeimi H, Alishahi N, J. Chin. Chem. Soc., 59, 1001 (2012)

[23] Naeimi H, Alishahi N, J. Chem. Res., 208 (2013)

[24] Naeimi H, Alishahi N, J. Exp. Nanosci., http://dx.doi.org/10.1080/17458080.2013.822575 (2013)

[25] Navarrete-Vazquez G, Moreno-Diaz H, Aguirre-Crespo F, Leon-Rivera I, Villalobos-Molina R, Munoz-Munizd O, Estrada-Sotoa S, Bioorg. Med. Chem. Lett., 16, 4169 (2006)

[26] Yu J, Xu J, Lu M, Appl. Organomet. Chem., 27, 606 (2013)

[27] Rostamizadeh S, Aryan R, Ghaieni HR, Amani AM, J. Heterocycl. Chem., 46, 74 (2009)