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Catalyst‐free Synthesis of Spiro[indoline‐3,1′‐pyrazolo[5,1‐a]isoquinolines] via Diastereoselective 1,3‐dipolar Cycloaddition under Mild Conditions
Author(s) -
Hu Fangzhi,
Chen Hui,
Zhang Minmin,
Yu Shuowen,
Xu Xiaoying,
Yuan Weicheng,
Zhang Xiaomei
Publication year - 2017
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2903
Subject(s) - chemistry , cycloaddition , indoline , catalysis , 1,3 dipolar cycloaddition , combinatorial chemistry , organic chemistry
A highly efficient catalyst‐free1,3‐dipolar cycloaddition reaction of methyleneindolinones and C , N ‐cyclic azomethine imines was realized. The reactions afforded a large variety of spirooxindoles in high yields (up to 99%) and excellent diastereoselectivities (dr > 20:1). Furthermore, the configuration of one of the products was determined on the basis of X‐ray structural analysis. Accordingly, a possible transition‐state model was proposed.