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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 23
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Original Articles

Regioselective Synthesis of 1,8-Naphthyridinone-Annulated Oxygen and Sulfur Heterocycles by Tri-n-butyl Tinhydride–Mediated Aryl Radical Cyclization

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Pages 4053-4067 | Received 02 Apr 2008, Published online: 31 Oct 2008
 

Abstract

The tin hydride–mediated cyclizations of a number of ethers, sulfides, and sulfones under mild, neutral conditions have been investigated. While the 2-bromobenzyloxy ethers were prepared in 62–65% yields by the alkylation of 4-hydroxy-1-phenyl-1,8-naphthyridin-2(1H)-one with 2-bromobenzyl bromides in refluxing acetone in the presence of anhydrous potassium carbonate, the sulfides were derived from 4-mercapto-1-phenyl-1,8-naphthyridin-2(1H)-one and 2-bromobenzyl bromides in 82–84% yields by a phase-transfer catalysis (PTC) reaction. The corresponding sulfones were prepared by treatment of the sulfides with m-CPBA in refluxing dichloromethane. The ethers, sulfides, and the sulfones were treated with n Bu3SnH-AIBN to give regioselectively 1,8-naphthyridinone-annulated oxygen and sulfur heterocycles in 70–78% yields.

ACKNOWLEDGMENT

We thank the CSIR (New Delhi) and the DST (New Delhi) for financial assistance. One of us (R. I.) is thankful to CSIR (New Delhi) for a senior research fellowship.

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