Efficient Synthesis of Benzothiazolone Derivatives by a Domino Reaction of Disulfide and COS under Mild Conditions. Issue 48 (5th December 2018)

• Record Type: Journal Article
• Authors: Zhou, Bohao; Hong, Hailong; Wang, Hongcai; Zhang, Tianmiao; Han, Limin; Zhu, Ning
• Is Part Of: European journal of organic chemistry. Issue 48(2018)
• Page Start: 6983
• Page End: 6990
• Publication Date: 2018-12-05
• Subjects: Synthesis design -- Domino reactions -- COS -- Benzothiazolone derivatives -- Reaction mechanisms; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201801393
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Carbonyl sulfide (COS), whose molecular structure is similar to CO2 and CS2, could be used as a better alternative carbonyl reagent due to its high chemical activity. However, the unfriendly by‐product H2 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 H2 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. Abstract : An efficient method for preparing benzothiazolone derivatives was developed by a domino coupling reaction between the disulfide and COS in the present of NaOH. Notably, the C=O of COS was converted into benzothiazolone by carbonylation reaction and the sulfur of COS was transformed into sulfur and sulfide after cleaving the S–S bond under mild conditions. This efficient synthetic methodology could provide a promising process for the utilization of COS.