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-Benzodiox

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• 作者：Sukalyan Bhadra ; Laksmikanta Adak ; Subhas Samanta ; A. K. M. Maidul Islam ; Manabendra Mukherjee ; Brindaban C. Ranu
• 刊名：Journal of Organic Chemistry
• 出版年：2010
• 出版时间：December 17, 2010
• 年：2010
• 卷：75
• 期：24
• 页码：8533-8541
• 全文大小：1129K
• 年卷期：v.75,no.24(December 17, 2010)
• ISSN：1520-6904

文摘

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.