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Angew Chem Int Ed Engl. 2017 Jul 24;56(31):9183-9187. doi: 10.1002/anie.201703967. Epub 2017 Jul 5.

Synthesis of [5,6]-Bicyclic Heterocycles with a Ring-Junction Nitrogen Atom: Rhodium(III)-Catalyzed C-H Functionalization of Alkenyl Azoles.

Author information

1
Department of Chemistry, Yale University, 225 Prospect St., New Haven, CT, 06520, USA.

Abstract

The first syntheses of privileged [5,6]-bicyclic heterocycles, with ring-junction nitrogen atoms, by transition metal catalyzed C-H functionalization of C-alkenyl azoles is disclosed. Several reactions are applied to alkenyl imidazoles, pyrazoles, and triazoles to provide products with nitrogen incorporated at different sites. Alkyne and diazoketone coupling partners give azolopyridines with various substitution patterns. In addition, 1,4,2-dioxazolone coupling partners yield azolopyrimidines. Furthermore, the mechanisms for the reactions are discussed and the utility of the developed approach is demonstrated by iterative application of C-H functionalization for the rapid synthesis of a patented drug candidate.

KEYWORDS:

C−H activation; cyclization; homogeneous catalysis; nitrogen heterocycles; rhodium

PMID:
28586164
PMCID:
PMC5564303
DOI:
10.1002/anie.201703967
[Indexed for MEDLINE]
Free PMC Article

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