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Issue 19, 2016
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In situ generation and trapping of thioimidates: an intermolecular tandem reaction to 4-acylimino-4H-3,1-benzothiazines

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Abstract

The proton-catalyzed transformation of 2-thioureidobenzonitriles to 4-acylimino-4H-3,1-benzothiazines was accomplished by treatment with carboxylic anhydrides, acid chlorides or alkyl chloroformates. The reaction involves a cyclization to 4-imino-3,1-benzothiazinium salts, whose thioimidate structure is trapped by a subsequent reaction with the acyl donor. 2-Ureidobenzonitriles do not undergo such an intermolecular tandem reaction. The different reaction behavior of both types of substrates was verified by NMR monitoring and employing 18O-enriched water.

Graphical abstract: In situ generation and trapping of thioimidates: an intermolecular tandem reaction to 4-acylimino-4H-3,1-benzothiazines

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Publication details

The article was received on 04 Jan 2016, accepted on 27 Jan 2016 and first published on 29 Jan 2016


Article type: Paper
DOI: 10.1039/C6RA00196C
RSC Adv., 2016,6, 15430-15440

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    In situ generation and trapping of thioimidates: an intermolecular tandem reaction to 4-acylimino-4H-3,1-benzothiazines

    C. Steinebach, A. Schulz-Fincke, G. Schnakenburg and M. Gütschow, RSC Adv., 2016, 6, 15430
    DOI: 10.1039/C6RA00196C

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