Access to [2,1]Benzothiazine S,S-Dioxides from β-Substituted o-Nitrostyrenes and Sulfur

Autor:	Dinh Hung Mac, Satoki Koyama, Thanh Binh Nguyen, Hoang Anh Cao, Thi Mo Nguyen, Thi Thuong Thuong Cao
Přispěvatelé:	Institut de Chimie des Substances Naturelles (ICSN), Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)
Rok vydání:	2020
Předmět:	inorganic chemicals 010405 organic chemistry Chemistry Organic Chemistry chemistry.chemical_element Benzothiazine 010402 general chemistry 01 natural sciences Medicinal chemistry Sulfur 0104 chemical sciences chemistry.chemical_compound Atom economy [CHIM]Chemical Sciences
Zdroj:	Journal of Organic Chemistry Journal of Organic Chemistry, American Chemical Society, 2020, 85 (19), pp.12058-12066. ⟨10.1021/acs.joc.0c00918⟩
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.0c00918
Popis:	International audience; Benzothiazine S,S-dioxides 2 were synthesized by simply heating o-nitrostyrenes with elemental sulfur in 3-picoline with complete atom economy. This reaction was found to occur without any added catalyst and consist of a cascade of reduction of the nitro group, sulfuration of a C-H of the double bond, oxidation of a sulfur atom to its highest oxidation state by the migration of two oxygen atoms from the nitro group and formation of new N-S bond. Furthermore, the method could also be applied to o-nitrocinnamamides and cinnamate esters.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::d9920f7e41ac6f8fecc486fd6c27eb4d https://doi.org/10.1021/acs.joc.0c00918 Zobrazit plný text záznamu