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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 21
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Original Articles

Unexpected Rearrangement in the Reaction of 7‐Mercapto‐4‐methylcoumarin with 1‐Mono‐ and 1,1‐Dimethyl Propargyl Alcohols

Shiqing Xu Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai, China
,
Xin Yan Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai, China
,
Qian Zhang Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai, China
,
Peng Xia Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai, ChinaCorrespondence[email protected] and [email protected]
&
Ying Chen Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai, China
Pages 3801-3808 | Received 07 Mar 2007, Published online: 19 Oct 2007
 
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Abstract

The reaction of 7‐mercapto‐4‐methylcoumarin (4) with 1‐mono‐ and 1,1‐dimethyl propargyl alcohols in H3PO4 afforded the corresponding β‐(7‐coumarinthio)ketones with a rearrangement of the carbon chain of propargyl. A possible mechanism of this rearrangement was proposed.

Acknowledgment

This research was supported by grants from the National Natural Science Foundation of China (Nos. 20272010 and 30200348) awarded to P. Xia and Y. Chen, respectively, and the research grant (No. 2002046069) from the National Education Administration of China awarded to P. Xia. In addition, we express our sincere thanks to Tamejiro Hiyama for his kind discussions.

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