Furan ring opening-indole ring closure: SnCl₂-induced reductive transformation of difuryl(2-nitroaryl)methanes into 2-(2-acylvinyl)indoles

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• 作者：Maxim G. Uchuskin^a ; Natalia V. Molodtsova^a ; Vladimir T. Abaev^b ; Igor V. Trushkov^c ; ^d ; Alexander V. Butin^a ; ^e ; ^{alexander_butin@mail.ru} ; ^{av_butin@yahoo.com}
• 关键词：Furans ; Ring opening ; Ring closure ; Indoles ; Reduction ; Nitroarenes ; Nitrosoarenes
• 刊名：Tetrahedron
• 出版年：2012
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：3 June, 2012
• 卷：68
• 期：22
• 页码：4252-4258
• 文件大小：332 K

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路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-thienyl)(2-nitroaryl)methanes under the same reaction conditions failed to undergo the analogous recyclization and were transformed into bis(5-alkyl-2-thienyl)(2-aminoaryl)methanes.