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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 10
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Original Articles

Regioselective Synthesis of 2H‐Benzothiopyrano[3,2‐c]quinolin‐7(8H)‐ones by Tri‐n‐butyltinhydride–Mediated Radical Cyclization

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Pages 1747-1756 | Received 16 Oct 2006, Published online: 22 May 2007
 

Abstract

A number of hitherto unreported 2H‐benzothiopyrano[3,2‐c]quinolin‐7(8H)‐ones have been regioselectively synthesized in 90–96% yield by tri‐n‐butyltinhydride–AIBN–mediated radical cyclization from 4‐(2′‐bromothioarylmethyl)‐1‐methylquinolin‐2(1H)‐ones and their corresponding sulfones. 4‐(2′‐Bromothioarylmethyl)quinolin‐2(1H)‐ones were in turn prepared from 4‐bromomethylquinolin‐2(1H)‐one and o‐bromothiophenols by refluxing in acetone in the presence of anhydrous K2CO3. These were converted to the corresponding sulfones by oxidation with two equivalents of m‐CPBA in refluxing dichloromethane for 1 h.

Acknowledgments

N. Kundu is thankful to Council of Scientific and Industrial Research (CSIR) (New Delhi) for a senior research fellowship. We also thank Department of Science and Technology (DST) (New Delhi) for providing a UV‐Vis spectrophotometer and FT‐IR spectrometer under the Department of Science and Technology‐Financial assistance for Infrastructural Development of Science and Technology (DST‐FIST) program.

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