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

被引：1

作者：

Cao, Zhihao ^{[1
,2
,3
]}

Zhu, Ning ^{[1
,2
,3
]}

Li, Shuyi ^{[1
,2
,3
]}

Wang, Xinchen ^{[1
,2
,3
]}

Xie, Ruijun ^{[1
,2
,3
,4
]}

机构：

[1] Inner Mongolia Univ Technol, Coll Chem Engn, Hohhot, Peoples R China

[2] Key Lab CO2 Resource Utilizat Univ Inner Mongolia, Hohhot, Peoples R China

[3] Inner Mongolia Engn Res Ctr CO2 Capture & Utilizat, Hohhot, Peoples R China

[4] Inner Mongolia Univ Technol, Coll Chem Engn, Hohhot 010051, Peoples R China

来源：

SYNTHETIC COMMUNICATIONS | 2023年 / 53卷 / 20期

基金：

中国国家自然科学基金;

关键词：

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

D O I：

10.1080/00397911.2023.2246085

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

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.

引用

页码：1739 / 1750

页数：12

共 22 条

[1]

[Anonymous], 1991, Heteroat. Chem.

[2] One-Pot Synthesis of Quinazolinone Derivatives from Nitro-Compounds with the Aid of Low-Valent Titanium [J].