Substituted Pyrrololactams via Ring Expansion of Spiro-2H-pyrroles from Intermolecular Alkyne–Isocyanide Click Reactions

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• 作者：Jimil George ; Hun Young Kim ; Kyungsoo Oh
• 刊名：Organic Letters
• 出版年：2017
• 出版时间：February 3, 2017
• 年：2017
• 卷：19
• 期：3
• 页码：628-631
• 全文大小：415K
• ISSN：1523-7052

文摘

The facile synthesis of 6- to 8-membered pyrrololactams has been developed using a ring expansion of spiro-2H-pyrroles, the products of intermolecular alkyne–isocyanide click reactions. The key to successful ring expansion of spiro-2H-pyrroles to pyrrololactams is the enforced orbital overlap between the internal alkene and the amide carbonyl group through the conformationally locked bicyclic structures. The newly disclosed α-isocyano lactams, substrates for click reactions, should find their utility in the synthesis of pharmaceutically important heterocyclic compounds.