Regioselectivity in the 1, 3??dipolar cycloaddition reaction of unsymmetric pyridinium dicyanomethylides with dimethyl acetylenedicarboxylate and methyl propiolate: …

K Matsumoto, Y Ikemi, H Konishi, XL Shi…

Index: Matsumoto, Kiyoshi; Ikemi, Yukio; Konishi, Hideyuki; Shi, Xiao-lan; Uchida, Takane; Aoyama, Kinuyo Journal of Heterocyclic Chemistry, 1988 , vol. 25, # 2 p. 689 - 692

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Citation Number: 5

Abstract

Abstract A study of the cycloaddition behavior of a series of unsymmetric pyridinium dicyanomethylides with dimethyl acetylenedicarboxylate and methyl propiolate has been carried out. The 1, 3-dipolar cycloaddition proceeds in good yield with high regioselectivity to produce the corresponding indolizines and 1: 1 adducts. The reactions of isoquinolinium dicyanomethylide follow frontier orbital predictions. In contrast, polar 3-substituted ...