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Synthesis 2021; 53(07): 1237-1246
DOI: 10.1055/s-0040-1706105
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Synthesis of Pyrrolo[1,2-a][1,6]- and [1,8]naphthyridines by Alkyne-Carbonyl Metathesis

Marian Blanco Ponce
a   Institute of Chemistry, University of Rostock, A.-Einstein-Str. 3a, 18059 Rostock, Germany
b   University of Granma, Centre for Study of Applied Chemistry, Carretera Manzanillo Km 17½, 85100, Bayamo, Cuba
,
Silvio Parpart
a   Institute of Chemistry, University of Rostock, A.-Einstein-Str. 3a, 18059 Rostock, Germany
,
Alexander Villinger
a   Institute of Chemistry, University of Rostock, A.-Einstein-Str. 3a, 18059 Rostock, Germany
,
Eugenio Torres Rodríguez
b   University of Granma, Centre for Study of Applied Chemistry, Carretera Manzanillo Km 17½, 85100, Bayamo, Cuba
,
Peter Ehlers  ∗
a   Institute of Chemistry, University of Rostock, A.-Einstein-Str. 3a, 18059 Rostock, Germany
c   Leibniz-Institute for Catalysis, A.-Einstein-Str. 29, 18059 Rostock, Germany
,
Peter Langer  ∗
a   Institute of Chemistry, University of Rostock, A.-Einstein-Str. 3a, 18059 Rostock, Germany
c   Leibniz-Institute for Catalysis, A.-Einstein-Str. 29, 18059 Rostock, Germany
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Abstract

A concise and modular synthesis of pyrrolo[1,2-a][1,6]- and [1,8]naphthyridines by a one-pot two-step reaction consisting of electrophilic acylation followed by an alkyne-carbonyl-metathesis reaction as the final cyclization step is reported. This developed synthetic methodology allows the facile synthesis of these heterocyclic core structures in mainly high overall yields under metal-free conditions. Reaction conditions are carefully optimized and display a novel supplement to access these tricyclic heterocyclic compounds.

Key words

acylation - alkyne-carbonyl metathesis - Brønsted acid - cyclization - pyrrolonaphthyridines

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706105.
  • Supporting Information


Publication History

Received: 08 October 2020

Accepted after revision: 19 November 2020

Article published online:
21 December 2020

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
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