Tetrahedron

Furan ring opening–indole ring closure: SnCl 2-induced reductive transformation of difuryl (2-nitroaryl) methanes into 2-(2-acylvinyl) indoles

MG Uchuskin, NV Molodtsova, VT Abaev, IV Trushkov…

文献索引：Uchuskin, Maxim G.; Molodtsova, Natalia V.; Abaev, Vladimir T.; Trushkov, Igor V.; Butin, Alexander V. Tetrahedron, 2012 , vol. 68, # 22 p. 4252 - 4258

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被引用次数: 21

摘要

A simple and efficient method for the synthesis of 2-(2-acylvinyl)-3-(5-alkyl-2-furyl) indoles by reductive recyclization of bis (5-alkyl-2-furyl)(2-nitroaryl) methanes is reported. This transformation was carried out by heating the substrates with SnCl2· 2H2O in ethanol. The intermediate nitrosoarene moiety interacted with the furan ring via electrophilic nitrogen attack onto the C (2) position of the furan ring. It was shown that the related bis (5-alkyl-2- ...