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Construction of Novel Tetrahydro‐ β ‐carboline‐1‐thione Spirooxindoles by Brønsted Acid Mediated Formal [3+3] Cyclization of 3‐Indolylmethanols with 3‐Isothiocyanato Oxindoles
Author(s) -
Liao Yijun,
Bai Mei,
Yu Shuowen,
Zhang Minmin,
Hu Fangzhi,
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.2708
Subject(s) - chemistry , stereochemistry , p toluenesulfonic acid , combinatorial chemistry , transformation (genetics) , medicinal chemistry , organic chemistry , catalysis , biochemistry , gene
p ‐Toluenesulfonic acid mediated formal [3+3] cyclization of 3‐indolylmethanols with 3‐isothiocyanato oxindoles was realized. This transformation allowed for the synthesis of a series of novel tetrahydro‐ β ‐carboline‐1‐thione spirooxindoles in moderate to excellent yields (up to 99%) with generally good diastereoselectivities (up to >20:1). The structure of one product was determined by an X‐ray crystal structural analysis.