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Synthesis 2012; 44(16): 2607-2613
DOI: 10.1055/s-0032-1316563
paper
© Georg Thieme Verlag Stuttgart · New York

Hydrothiolation and Intramolecular Cyclization Sequence for the Synthesis of 1,3-Oxathiine Frameworks

Yuta Nishina*
Research Core for Interdisciplinary Sciences, Okayama University, Tsushima, Kita-ku, Okayama 700-8530, Japan, Fax: +81(86)2518718   Email: nisina-y@cc.okayama-u.ac.jp
,
Junya Miyata
Research Core for Interdisciplinary Sciences, Okayama University, Tsushima, Kita-ku, Okayama 700-8530, Japan, Fax: +81(86)2518718   Email: nisina-y@cc.okayama-u.ac.jp
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Publication History

Received: 17 April 2012

Accepted after revision: 25 May 2012

Publication Date:
03 July 2012 (online)

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Abstract

1,3-Oxathiine frameworks can be prepared via the sequential addition and intramolecular cyclization of thiosalicylic acid onto alkynes. A substituent on the alkyne and the presence of a palladium catalyst can allow product regioselectivity control. This strategy is applicable to the synthesis of heterocycles comprising sulfur and oxygen atoms, namely 3,1-benzoxathiines, without any unwanted byproduct.

Key words

heterocycles - hydrothiolation - palladium - sequential reaction - alkynes - 3,1-benzoxathiines

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
  • Supporting Information
 

  • References


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