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Licensed Unlicensed Requires Authentication Published by De Gruyter November 13, 2020

Selective cyclization modes of methyl 3′-heteroarylamino-2′-(2,5-dichlorothiophene-3-carbonyl)acrylates. Synthesis of model (thienyl)pyrazolo- and triazolo[1,5-α]pyrimidines

  • Nuha I. Sweidan , Mustafa M. El-Abadelah , Musa Z. Nazer and Wolfgang Voelter EMAIL logo

Abstract

Interaction of methyl 3-ethoxy-2-(2,5-dichloro-3-thenoyl)acrylate (I) with 3-aminopyrazole and 3-amino-1,2,4-triazole generated the respective pyrazolo[1,5-α]pyrimidine (4) and triazolo[1,5-α]pyrimidine (7). The formation of 4 entails selective and consecutive displacement of the 3-ethoxy and methoxy (ester) anions in I by 3-NH2 and 1-NH of 3-aminopyrazole. On the other hand, the formation of 7 implies selective displacement of 3-ethoxy in I by the ring-NH followed by cyclocondensation involving the keto group in I and 3-NH2 of aminotriazole. This latter selective displacement sequence is also followed by 3-amino-5-hydroxypyrazole in its reaction with I. The structures of the new compounds are supported by microanalytical and spectral data.


Corresponding author: Wolfgang Voelter, Interfakultäres Institut für Biochemie, Universität Tübingen, Hoppe-Seyler Straße 4, 72076Tübingen, Germany, E-mail:

Funding source: University of Jordan

Acknowledgments

We wish to thank the Deanship of Scientific Research at the University of Jordan, Amman-Jordan, for financial support.

  1. Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: The Deanship of Scientific Research at the University of Jordan, Amman-Jordan.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Received: 2020-07-12
Accepted: 2020-10-12
Published Online: 2020-11-13
Published in Print: 2020-12-16

© 2020 Walter de Gruyter GmbH, Berlin/Boston

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