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Updated: Jul 3, 2025

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
Annulations of Ynamides with 1,2-Benzisothiazoles to Construct 1,4-Benzothiazepines and 3-Aminoisoquinolines
Xiao-Na Wang1, Zhen Zhao1, Jinyue Chen1
1Key Laboratory of Advanced Drug Preparation Technologies, Ministry of Education, School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou, Henan 450001, P.R. China.
Abstract:
Two distinct TMSOTf-catalyzed annulation reactions between ynamides and 1,2-benzisothiazoles have been developed. The direction of the reaction could be easily switched by applying different thermodynamic-controlled conditions. At room temperature, ynamides undergo a [5 + 2] annulation reaction with 1,2-benzisothiazoles to afford 1,4-benzothiazepines, whereas under heating conditions a desulfurizative annulation reaction proceeds well to access 3-aminoisoquinolines. These two protocols provide biologically important 1,4-benzothiazepines and 3-aminoisoquinolines with high efficiency with broad substrate scopes under mild reaction conditions.
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