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Use of dodecanoyl isothiocyanate as building block in synthesis of target benzothiazine, quinazoline, benzothiazole and thiourea derivatives

  • Magdy M. Hemdan EMAIL logo and Eman A. El-Bordany
Published/Copyright: March 31, 2016
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Chemical Papers
From the journal Chemical Papers Volume 70 Issue 8

Abstract

Dodecanoyl isothiocyanate (I) reacts additively with anthranilic acid to afford derivatives of thiourea II and benzothiazine III in a one-pot reaction. The cyclisation of thiourea II was achieved using acetic anhydride to form quinazoline derivative IV. The heating of quinazoline IV in acetic anhydride or butan-1-ol gave quinazoline derivatives V or VI, respectively. Benzothiazine III underwent trans-acylation to benzothiazine VII in boiling acetic anhydride. The treatment of IV with hydrazine hydrate, anthranilic acid or ethyl carbazate afforded derivatives of triazoloquinazoline VIII, quinazolinoquinazoline XI or thiosemicarbazide X, respectively. The reaction of I with 2aminophenol or 2-aminothiophenol afforded thiourea derivative XIII or benzothiazole derivative XIV, respectively. Most of the synthesised compounds bear a lauroyl (dodecanoyl) group (a hydrocarbon moiety). The structures of the synthesised compounds were confirmed by microanalytical and spectral data.

Keywords: lauroyl isothiocyanate; thiourea; benzothiazine; quinazoline; thiosemicarbazide derivatives

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Received: 2015-8-15
Revised: 2015-12-7
Accepted: 2015-12-16
Published Online: 2016-3-31
Published in Print: 2016-8-1

© 2016 Institute of Chemistry, Slovak Academy of Sciences

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https://doi.org/10.1515/chempap-2016-0042
Keywords for this article
lauroyl isothiocyanate; thiourea; benzothiazine; quinazoline; thiosemicarbazide derivatives

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