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

作者：Bhadra Sukalyan; Adak Laksmikanta; Samanta Subhas; Islam A K M Maidul; Mukherjee Manabendra; Ranu Brindaban C^*

来源：Journal of Organic Chemistry, 2010, 75(24): 8533-8541.

DOI：10.1021/jo101916e

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.

• 出版日期2010-12-17