One-Pot Synthesis of 2-R-Naphtho[2,3-b]thiophene-4,9-diones via Cyclization of 2-(R-Ethynyl)-1,4-naphthoquinones with Na2S2O3

Autor:	Yurii V. Gatilov, Denis S. Baranov, Alexander Popov, Danil A. Nevostruev, Elena S. Kobeleva, Alexey A. Dmitriev
Rok vydání:	2021
Předmět:	Bunte salt chemistry.chemical_compound Chemistry Organic Chemistry One-pot synthesis Thiophene Organic chemistry
Zdroj:	The Journal of Organic Chemistry. 86:11361-11369
ISSN:	1520-6904 0022-3263
Popis:	The concise and efficient one-pot synthesis of 2-R-naphtho[2,3-b]thiophene-4,9-diones from 2-bromo-1,4-naphthoquinone and alkynes has been developed. The reaction proceeds through the formation of 2-(R-ethynyl)-1,4-naphthoquinones, which undergo transformation with Na2S2O3 to 2-R-naphtho[2,3-b]thiophene-4,9-diones via C-H sulfuration, accompanied by the formation of the aromatic Bunte salt, followed by its air oxidation and 5-endo-dig cyclization. The protocol is characterized by simplicity, good tolerance for functional groups, relatively mild conditions, and commercially available starting compounds.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::ada40c65d6e27c3498f628b9393f348f https://doi.org/10.1021/acs.joc.1c00852 Zobrazit plný text záznamu