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,The Journal of Organic Chemistry

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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
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2021-08-04 , DOI: 10.1021/acs.joc.1c00852
Denis S Baranov ₁ , Alexander A Popov ₁ , Danil A Nevostruev ₁ , Alexey A Dmitriev ₁ , Yurii V Gatilov ₂ , Elena S Kobeleva ₁

Affiliation

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.

中文翻译：

通过 Na2S2O3 环化 2-(R-Ethynyl)-1,4-naphthoquinones 一锅法合成 2-R-Naphtho[2,3-b]thiophene-4,9-diones

已经开发了从 2-溴-1,4-萘醌和炔烃中简明高效地一锅法合成 2- R-萘并[2,3 - b ]噻吩-4,9-二酮的方法。该反应通过形成 2-( R -乙炔基)-1,4-萘醌，其与 Na ₂ S ₂ O ₃转化为 2- R -萘并[2,3- b ]噻吩-4,9-二酮通过 C-H 硫化，伴随着芳香族 Bunte 盐的形成，然后是空气氧化和 5-endo-dig 环化。该协议的特点是简单、对官能团具有良好的耐受性、相对温和的条件和市售的起始化合物。

更新日期：2021-09-03

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