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One-Pot Double-Annulation Strategy for the Synthesis of Unusual Fused Bis-Heterocycles.
- Source :
-
Organic letters [Org Lett] 2020 Jun 05; Vol. 22 (11), pp. 4350-4354. Date of Electronic Publication: 2020 May 15. - Publication Year :
- 2020
-
Abstract
- A novel metal-free double-annulation cascade for the construction of unusual fused heterocyclic systems is described. This simple protocol enables the sequential assembly of two rings in one pot from two simple precursors. Acidic conditions promote the condensation and the intramolecular alkynyl Prins reaction of an enyne or arenyne alcohol with a cyclic hemiaminal to form a five-, six-, or seven-membered oxacycle followed by a seven- or eight-membered azacycle. In this transformation, chemical complexity is rapidly generated with the formation of three new bonds (one C-O, one C-C, and one C-N) in one synthetic operation. The strategy is modular and relatively general, providing access to a series of unique fused bicyclic scaffolds.
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 22
- Issue :
- 11
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 32412769
- Full Text :
- https://doi.org/10.1021/acs.orglett.0c01351