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氧化铝负载的 Cu(II),一种多功能、可回收的催化剂,用于区域选择性开环氮丙啶和环氧化物,随后环化生成功能化的 1,4-苯并恶嗪和 1,4-苯并二氧杂环己烷。

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.

机构信息

Department of Organic Chemistry, Indian Association for theCultivation of science, Jadavpur, Kolkata-700031, India.

出版信息

J Org Chem. 2010 Dec 17;75(24):8533-41. doi: 10.1021/jo101916e. Epub 2010 Nov 11.

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.

摘要

一种易于获得的催化剂,氧化铝负载的铜(II),高效地催化了氮丙啶和环氧化物的开环反应,随后通过相应中间体的环化反应,分别高产率地一锅法合成了各种官能化的 1,4-苯并恶嗪和 1,4-苯并二恶烷,无需任何配体。氮丙啶和环氧化物的环裂解具有高度的区域选择性。该催化剂价格低廉、非空气敏感、环境友好且可回收利用。提出了催化剂的功能和反应途径。该方案成功地用于一锅法形成三个碳杂原子键,即 C-O、C-N 和 C-S。

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