Efficient synthesis of thioquinazolinedione derivatives via the reaction of 2-aminobenzonitrile and carbonyl sulfide catalyzed by NaHS

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作   者：

Cao, Zhihao;  Zhu, Ning;  Li, Shuyi;  Wang, Xinchen;  Xie, Ruijun; 

作者机构：

Inner Mongolia Univ Technol;  Inner Mongolia Engn Res Ctr CO2 Capture & Utilizat; 

关键词：

QUINAZOLINE-2,4(1H,3H)-DIONES;  ONE-POT;  Synthetic method;  CO2;  DIOXIDE;  CHEMISTRY;  carbonyl sulfide;  NaHS;  thioquinazolinedione;  >; 

期刊名称：

Synthetic Communications

i s s n：

0039-7911

年卷期：

2023 年 53 卷 17/20 期

页   码：

1739-1750

页   码：

摘   要：

An efficient method for the synthesis of thioquinazolinediones from 2-aminobenzonitriles and carbonyl sulfide (COS) catalyzed by NaHS was established. In this synthetic method, NaHS was used to catalyze the reaction of COS with a broad range of 2-aminobenzonitrile to form the corresponding thioquinazolinedione. Moreover, the controlled experiments demonstrated that NaHS not only reacted with 2-aminobenzonitrile to form 2-aminobenzothioamide, but also acted as a strong nucleophile to react with COS to form the active intermediate dithiocarbonate. Subsequently, 2-aminobenzothioamide reacted with dithiocarbonate to form the thioquinazolinedione easily. Meanwhile, the generated H2S was recycled as sulfur source and hydrogen source to produce 2-aminobenzothioamide.