Journal
SYNTHESIS-STUTTGART
Volume 49, Issue 17, Pages 4065-4081Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0036-1588454
Keywords
pyrroles; acylacetylenes; enaminones; intramolecular cyclization; pyrrolo[1,2-a]pyrazines
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Funding
- Russian Federation (programs for the support of leading scientific schools) [NSh-7145.2016.3]
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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.
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