RSC Advances

Divergent reactivities of o-haloanilides with CuO nanoparticles in water: a green synthesis of benzoxazoles and o-hydroxyanilides

N Khatun, S Guin, SK Rout, BK Patel

Index: Khatun, Nilufa; Guin, Srimanta; Rout, Saroj Kumar; Patel, Bhisma K. RSC Advances, 2014 , vol. 4, # 21 p. 10770 - 10778

Full Text: HTML

Citation Number: 13

Abstract

In the present study, three divergent reaction paths emerged when o-haloanilides were subjected to CuO nanoparticles in water. o-Halo (I, Br) phenylbenzamides in the presence of CuO nanoparticles and Cs2CO3 in water at 100° C provided o-hydroxyphenyl benzamides as the major product. However, a complete change in selectivity was observed in the presence of an organic base/ligand (TMEDA), giving 2-arylbenzoxazole as the exclusive ...

~68%

~73%

~58%

~88%

~65%

~51%

~9%

A green route for the synthesis of 2-substituted benzoxazole...

[Suresh, Dhanusu; Dhakshinamoorthy, Amarajothi; Pitchumani, Kasi Tetrahedron Letters, 2013 , vol. 54, # 48 p. 6415 - 6419]

Poly (ethylene glycol)-bound sulphonic acid as a novel catal...

[Chikhale, Rupesh V.; Pant, Amit M.; Menghani, Sunil S.; Wadibhasme, Pankaj G.; Khedekar, Pramod B. South African Journal of Chemistry, 2013 , vol. 66, p. 254 - 262]

Copper-catalyzed synthesis of benzoxazoles via a regioselect...

[Ueda, Satoshi; Nagasawa, Hideko Journal of Organic Chemistry, 2009 , vol. 74, # 11 p. 4272 - 4277]

Direct arylation of benzoxazole C–H bonds with iodobenzene d...

[Yu, Peng; Zhang, Guangyou; Chen, Fan; Cheng, Jiang Tetrahedron Letters, 2012 , vol. 53, # 34 p. 4588 - 4590]

Parallel synthesis of a library of benzoxazoles and benzothi...

[Evindar, Ghotas; Batey, Robert A. Journal of Organic Chemistry, 2006 , vol. 71, # 5 p. 1802 - 1808]