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Synthesis 2017; 49(17): 4065-4081
DOI: 10.1055/s-0036-1588454
DOI: 10.1055/s-0036-1588454
paper
Transition-Metal-Free Synthesis of Pyrrolo[1,2-a]pyrazines via Intramolecular Cyclization of N-Propargyl(pyrrolyl)enaminones
This work was supported by the President of the Russian Federation (programs for the support of leading scientific schools, grant NSh-7145.2016.3).Weitere Informationen
Publikationsverlauf
Received: 07. April 2017
Accepted after revision: 12. Mai 2017
Publikationsdatum:
11. Juli 2017 (online)
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]pyrazinesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588454.
- Supporting Information
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