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Article

Diversity-Oriented Synthesis of 3-Iodochromones and Heteroatom Analogues via ICl-Induced Cyclization

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Chengxiang Zhou, Anton V. Dubrovsky, and Richard C. Larock*

Department of Chemistry, Iowa State University, Ames, Iowa 50011

J. Org. Chem., 2006, 71 (4), pp 1626–1632

DOI: 10.1021/jo0523722

Publication Date (Web): January 12, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, larock@iastate.edu

Abstract

The ICl-induced cyclization of heteroatom-substituted alkynones provides a simple, highly efficient approach to various 3-iodochromones and analogues. This process is run under mild conditions, tolerates various functional groups, and generally provides chromones in good to excellent yields. Subsequent palladium-catalyzed transformations afford a rapid increase in molecular complexity and a convenient preparation of a wide range of functionally substituted chromones, furans, and polycyclic compounds. Iodothiochromenones and iodoquinolinones are also prepared by similar ICl-induced cyclizations.

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Published In Issue February 17, 2006
Received November 16, 2005

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Article

Diversity-Oriented Synthesis of 3-Iodochromones and Heteroatom Analogues via ICl-Induced Cyclization

Abstract

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Recommend & Share

Related Content

Synthesis of 3-Iodoindoles by the Pd/Cu-Catalyzed Coupling of N,N-Dialkyl-2-iodoanilines and Terminal Acetylenes, Followed by Electrophilic Cyclization

Regio- and Stereoselective Synthesis of Isoindolin-1-ones via Electrophilic Cyclization

Synthesis of Polycyclic Aromatics and Heteroaromatics via Electrophilic Cyclization

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