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Efficient Synthesis of Benzothiazolone Derivatives by a Domino Reaction of Disulfide and COS under Mild Conditions
Author(s) -
Zhou Bohao,
Hong Hailong,
Wang Hongcai,
Zhang Tianmiao,
Han Limin,
Zhu Ning
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801393
Subject(s) - chemistry , reagent , carbonylation , carbonyl sulfide , yield (engineering) , domino , disulfide bond , sulfur , sulfide , organic chemistry , thiol , bond cleavage , combinatorial chemistry , chemical synthesis , medicinal chemistry , catalysis , carbon monoxide , materials science , biochemistry , metallurgy , in vitro
Carbonyl sulfide (COS), whose molecular structure is similar to CO 2 and CS 2 , could be used as a better alternative carbonyl reagent due to its high chemical activity. However, the unfriendly by‐product H 2 S would be generated when COS is used as a carbonyl reagent in the carbonylation reaction. In this report, the odorless and stable disulfide was used to replace the traditional foul smelling and unstable o ‐aminobenzenethiol to react with COS for preparing benzothiazolone derivatives in excellent yield, in which coupling reaction of H 2 S generation and S–S bond cleavage was firstly designed. Notably, the C=O of COS was converted into benzothiazolone derivatives by carbonylation reaction and the sulfur of COS was transformed into sulfur and sulfide after cleaving the S–S bond by a domino reaction of disulfide and COS under mild conditions. This efficient synthetic methodology provided a promising process for the utilization of COS.