Alumina-supported Cu(II), a versatile and recyclable catalyst for regioselective ring opening of aziridines and epoxides and subsequent cyclization to functionalized 1,4-benzoxazines and 1,4-benzodioxanes

Bhadra, Sukalyan ; Adak, Laksmikanta ; Samanta, Subhas ; Islam, A. K. M. Maidul ; Mukherjee, Manabendra ; Ranu, Brindaban C. (2010) Alumina-supported Cu(II), a versatile and recyclable catalyst for regioselective ring opening of aziridines and epoxides and subsequent cyclization to functionalized 1,4-benzoxazines and 1,4-benzodioxanes The Journal of Organic Chemistry, 75 (24). pp. 8533-8541. ISSN 0022-3263

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo101916e

Related URL: http://dx.doi.org/10.1021/jo101916e

Abstract

An easily accessible catalyst, alumina-supported copper(II), efficiently catalyzes the ring opening of aziridines and epoxides followed by cyclization of the corresponding intermediate to produce a variety of functionalized 1,4-benzoxazines and 1,4-benzodioxanes, respectively, in one pot without any ligand in high yields. The ring cleavages of aziridines and epoxides are highly regioselective. The catalyst is inexpensive, non-air-sensitive, environmentally friendly, and recyclable. The function of the catalyst and the reaction pathway are postulated. This protocol is successfully utilized for the formation of three carbon-heteroatom bonds, namely, C-O, C-N, and C-S, in one pot.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:41476
Deposited On:30 May 2011 05:36
Last Modified:30 May 2011 05:36

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