Intramolecular dehydrogenative C–S bond coupling of thioamides to form 1, 3-benzothiazines under metal-free conditions. Issue 13 (13th March 2019)

• Record Type: Journal Article
• Authors: Wen, Li-Rong; Zhou, Cheng-Cheng; Zhu, Ming-Zhe; Xie, Shu-Guang; Guo, Wei-Si; Li, Ming
• Is Part Of: Organic & biomolecular chemistry. Volume 17:Issue 13(2019)
• Page Start: 3356
• Page End: 3360
• Publication Date: 2019-03-13
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c9ob00237e
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A new protocol for the synthesis of 1, 3-benzothiazines was developed through direct intramolecular dehydrogenative C–S bond coupling. Abstract : A novel HTIB-promoted direct intramolecular dehydrogenative C–S bond coupling reaction of thioamides has been developed to provide 1, 3-benzothiazine derivatives in good yields. The reaction proceeds smoothly to reach completion at room temperature within 1 min under metal-free conditions. This protocol provides a mild and efficient strategy for the synthesis of six-membered N, S-containing heterocycles. Preliminary mechanistic studies indicate that a spirocyclic intermediate might be involved.