Photochemical radical cyclization of γ,δ-unsaturated ketone oximes to 3,4-dihydro-2H-pyrroles

被引:44
作者
Kitamura, M [1 ]
Mori, Y [1 ]
Narasaka, K [1 ]
机构
[1] Univ Tokyo, Dept Chem, Grad Sch Sci, Bunkyo Ku, Tokyo 1130033, Japan
关键词
oxime; radical cyclization; photoinduced electron transfer; photoinduced energy transfer;
D O I
10.1016/j.tetlet.2005.02.062
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
3.4-Dihvdro-2H-pyrroles are synthesized from gamma,delta-unsaturated oximes by photochemical radical cyclization with 1,5-dimethoxynaphthatene (DMN) as the sensitizer. The cyclization of alkyl ketone O-acetyloximes proceeds via photosensitized electron transfer in the presence of acetic acid, while conjugated oximes of aryl and alpha,beta-unsaturated ketones are cyclized via energy transfer. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2373 / 2376
页数:4
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