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

Vijay Nair; Bini Mathew; A. U. Vinod; Joseph Swaroop Mathen; Sindu Ros; Rajeev S. Menon; R. Luxmi Varma; R. Srinivas

doi:10.1055/s-2003-38072

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Synthesis 2003(5): 0662-0664
DOI: 10.1055/s-2003-38072

SHORTPAPER

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

Vijay Nair*^a, Bini Mathew^a, A. U. Vinod^a, Joseph Swaroop Mathen^a, Sindu Ros^a, Rajeev S. Menon^a, R. Luxmi Varma^a, R. Srinivas^b
^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

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Publication History

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

Abstract
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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

References

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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.