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Intramolecular PIFA-Mediated Alkyne Amidation and Carboxylation Reaction

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Imanol Tellitu,* Sonia Serna,^† M. Teresa Herrero, Isabel Moreno, Esther Domínguez,* and Raul SanMartin

Departamento de Qumica Orgnica II, Facultad de Ciencia y Tecnologa, Universidad del Pas Vasco/Euskal Herriko Unibertsitatea (UPV/EHU), P.O. Box 644, 48080 Bilbao, Spain %imanol.tellitu@ehu.es

J. Org. Chem., 2007, 72 (4), pp 1526–1529

DOI: 10.1021/jo062320s

Publication Date (Web): January 18, 2007

To whom correspondence should be addressed. Phone: (34) 94 601 5438. Fax: (34) 94 601 2748.

†

Present address: Planta Piloto de Química Fina, Universidad de Alcalá, 28871 Alcalá de Henares, Spain.

Abstract

The hypervalent iodine reagent PIFA promotes the intramolecular electrophilic cyclization of easily accessible alkynylamides and alkynyl carboxylic acids, leading to the formation of pyrrolidinone and lactone skeletons, respectively, in a very efficient way. A synthetic study and a mechanistic proposal for these transformations are presented.

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Published In Issue February 16, 2007
Received November 10, 2006

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Intramolecular PIFA-Mediated Alkyne Amidation and Carboxylation Reaction

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Efficient Synthesis of Highly Substituted Pyrrolin-4-ones via PIFA-Mediated Cyclization Reactions of Enaminones

Palladium-Catalyzed Highly Diastereoselective Oxidative Cascade Cyclization Reactions

A Metal-Free Approach to the Synthesis of Indoline Derivatives by a Phenyliodine(III) Bis(trifluoroacetate)-Mediated Amidohydroxylation Reaction

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