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

Abstract

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.

Graphical Abstract

Keywords:

• carbonyl sulfide
• NaHS
• Synthetic method
• thioquinazolinedione

Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

We thank Natural Science Foundation of Inner Mongolia Autonomous Region [2021ZD02 and 2021MS02021], the National Natural Science Foundation of China [21865020], Program for Grassland Excellent Talents of Inner Mongolia Autonomous Region, Foundamental Research Funds for Inner Mongolia Universities [JY20220125] and Innovative Research Team in Universities of Inner Mongolia Autonomous Region [NMGIRT2212] for financial support.