Formal [4+2] cycloaddition of 3-ethoxycyclobutanones with azo compounds

被引：13
|
作者：
Shima, Yusuke [1 ]
Matsuo, Jun-ichi [1 ]
机构：
[1] Kanazawa Univ, Grad Sch Med Sci, Div Pharmaceut Sci, Kakuma Machi, Kanazawa, Ishikawa 9201192, Japan
来源：
TETRAHEDRON LETTERS | 2016年 / 57卷 / 36期
关键词：
Cycloaddition; Cyclobutanone; Azobenzene; Regioselectivity; Hydropyridazine; DIELS-ALDER REACTION; CYCLOBUTANE DERIVATIVES; ORGANIC-SYNTHESIS; RING; ROUTE; REACTIVITY; DIAZENES; CLEAVAGE; ACID;
D O I：
10.1016/j.tetlet.2016.07.087
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Azobenzenes reacted with 3-ethoxycyclobutanoes to give 2,3-dihydro-pyridazin-4(1H)-ones by using EtAlCl2 as a Lewis acid. Thus, ring cleavage of 3-ethoxycyclobutanones took place to form a zwitterionic intermediate by activation with EtAlCl2, and intermolecular formal [4+2] cycloaddition of the zwitterionic intermediate proceeded with azobenzenes to give 2,3-dihydro-pyridazin-4(1H)-ones after elimination of ethanol. Regioselectivity for cycloaddition of unsymmetrical azobenzenes, ring contraction and chemoselective reduction of 2,3-dihydro-pyridazin-4(1H)-ones, and [4+2] cycloaddition to 4-phenyl-1,2,4-triazolin-3,5-dione are also described. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4066 / 4069
页数：4
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