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Rapid construction of tricyclic tetrahydrocyclopenta[4,5]pyrrolo[2,3-b]pyridine via isocyanide-based multicomponent reaction
- Source :
- Beilstein Journal of Organic Chemistry, Vol 20, Iss 1, Pp 1436-1443 (2024)
- Publication Year :
- 2024
- Publisher :
- Beilstein-Institut, 2024.
-
Abstract
- An efficient protocol for the synthesis of polyfunctionalized tetrahydrocyclopenta[4,5]pyrrolo[2,3-b]pyridine-3,4b,5,6,7(1H)-pentacarboxylates was developed by a three-component reaction. In the absence of any catalyst, the three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates and 5,6-unsubstituted 1,4-dihydropyridines in refluxing acetonitrile afforded polyfunctionalized tetrahydrocyclopenta[4,5]pyrrolo[2,3-b]pyridine-3,4b,5,6,7(1H)-pentacarboxylates in high yields and with high diastereoselectivity. The reaction was finished by in situ generation of activated 5-(alkylimino)cyclopenta-1,3-dienes from addition of alkyl isocyanide to two molecules of but-2-ynedioates and sequential formal [3 + 2] cycloaddition reaction with 5,6-unsubstituted 1,4-dihydropyridine.
Details
- Language :
- English
- ISSN :
- 18605397
- Volume :
- 20
- Issue :
- 1
- Database :
- Directory of Open Access Journals
- Journal :
- Beilstein Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- edsdoj.10227e0da41938f63167d71a80ca0
- Document Type :
- article
- Full Text :
- https://doi.org/10.3762/bjoc.20.126