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Synthesis 2017; 49(17): 4065-4081
DOI: 10.1055/s-0036-1588454
paper
© Georg Thieme Verlag Stuttgart · New York

Transition-Metal-Free Synthesis of Pyrrolo[1,2-a]pyrazines via Intramolecular Cyclization of N-Propargyl(pyrrolyl)enaminones

Lyubov N. Sobenina
Unsaturated Heteroatomic Compounds Laboratory, A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation   Email: boris_trofimov@irioch.irk.ru
,
Elena F. Sagitova
Unsaturated Heteroatomic Compounds Laboratory, A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation   Email: boris_trofimov@irioch.irk.ru
,
Igor A. Ushakov
Unsaturated Heteroatomic Compounds Laboratory, A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation   Email: boris_trofimov@irioch.irk.ru
,
Boris A. Trofimov*
Unsaturated Heteroatomic Compounds Laboratory, A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation   Email: boris_trofimov@irioch.irk.ru
› Author AffiliationsThis work was supported by the President of the Russian Federation (programs for the support of leading scientific schools, grant NSh-7145.2016.3).
Further Information

Publication History

Received: 07 April 2017

Accepted after revision: 12 May 2017

Publication Date:
11 July 2017 (online)

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Abstract

A concise transition-metal-free strategy for the synthesis of pyrrolo[1,2-a]pyrazines with enone substituents has been developed. It includes the following key steps: (a) cross-coupling of pyrroles with acyl(bromo)acetylenes in solid alumina at room temperature to give 2-(acylethynyl)pyrroles; (b) addition of propargylamine to the above acetylenes to form the corresponding N-propargylenaminones; and (c) chemo- and stereoselective base-catalyzed (Cs2CO3/DMSO) intramolecular cyclization of the synthesized propargylic derivatives to form (acylmeth­ylidene)pyrrolo[1,2-a]pyrazines of Z-configuration.

Key words

pyrroles - acylacetylenes - enaminones - intramolecular cyclization - pyrrolo[1,2-a]pyrazines

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588454.
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