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Synthesis 2003(5): 0662-0664
DOI: 10.1055/s-2003-38072
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

[4 + 1] Cycloaddition Reactions of o-Thioquinones with Isocyanides: Novel Syntheses of 2-Imino-1,3-Oxathioles

Vijay Nair*a, Bini Mathewa, A. U. Vinoda, Joseph Swaroop Mathena, Sindu Rosa, Rajeev S. Menona, R. Luxmi Varmaa, R. Srinivasb
a Organic Chemistry Division, Regional Research Laboratory, CSIR, Trivandrum 695 019, Kerala, India
Fax: +91(471)2491712; e-Mail: vijaynair_2001@yahoo.com, gvn@csrrltrd.ren.nic.in;
b Mass spectrometry Center, IICT, Hyderabad 500 007, Andhra Pradesh, India
Further Information

Publication History

Received 18 October 2002
Publication Date:
21 March 2003 (online)

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Abstract

o-Thioquinones, generated in situ from o-hydroxyphenylthiophthalimides, underwent facile [4 + 1] cycloaddition reactions with isocyanides to afford 2-imino-1,3-oxathioles.

Key words

thioquinones - isocyanides - cycloadditions - 2-imino-1,3-oxathioles

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5

The ratio of the isomers was determined by the relative heights of the 13C signal of the carbon attached to the imino nitrogen.