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Synthesis 2018; 50(05): 1159-1165
DOI: 10.1055/s-0036-1589136
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© Georg Thieme Verlag Stuttgart · New York

Synthesis of New Annulated Pyrazinothienotriazolopyrimidinones and Triazolylthienopyrazines

Joana F. Campos
a   Departmento/Centro de Química, Escola de Ciências, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal
b   Institut de Chimie Organique et Analytique (ICOA), Université d’Orléans UMR-CNRS 7311, BP 6759, rue de Chartres 45067 Orléans cedex 2, France   Email: sabine.berteina-raboin@univ-orleans.fr
,
Maria-João R. P. Queiroz
a   Departmento/Centro de Química, Escola de Ciências, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal
,
Sabine Berteina-Raboin  *
b   Institut de Chimie Organique et Analytique (ICOA), Université d’Orléans UMR-CNRS 7311, BP 6759, rue de Chartres 45067 Orléans cedex 2, France   Email: sabine.berteina-raboin@univ-orleans.fr
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Further Information

Publication History

Received: 25 September 2017

Accepted after revision: 21 October 2017

Publication Date:
23 November 2017 (online)

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Abstract

New pyrazino[2′,3′:4,5]thieno[2,3-e][1,2,3]triazolo[1,5-a]-pyrimidin-5(4H)-ones were synthesized in an efficient, fast, and mild one-pot procedure from methyl 7-azidothieno[2,3-b]pyrazine-6-carboxylate. From the latter, some triazolothieno[2,3-b]pyrazine-6-carboxylates were also obtained with total regioselectivity by [2+3] cycloaddition with alkynes without any metal catalyst.

Key words

heterocycle - pyrazinothienopyrimidines - thienopyrazines - cycloaddition - one-pot cyclizations

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1589136.
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