Rh(III)-catalyzed C-H activation/cyclization of indoles and pyrroles: divergent synthesis of heterocycles.

doi:10.1021/jo500902n

Paper

Rh(III)-catalyzed C-H activation/cyclization of indoles and pyrroles: divergent synthesis of heterocycles.

Published Jun 26, 2014 · Yan Zhang, Jing Zheng, Sunliang Cui

The Journal of organic chemistry

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135

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Abstract

We report herein a new strategy of the Rh(III)-catalyzed C-H activation/cyclization of indoles and pyrroles, for the divergent synthesis of privileged heterocycles. A simple derivation of indoles and pyrroles to N-carboxamides with oxidative bidentate directing group could enable rhodacycle formation and late-stage redox-neutral cyclization with alkynes, alkenes and diazo compounds, for access to five- and six-membered fused heterocycles, such as pyrimido[1,6-a]indol-1(2H)-one, 3,4-dihydropyrimido[1,6-a]indol-1(2H)-one, and 1H-imidazo[1,5-a]indol-3(2H)-ones. Kinetic isotope effect study was conducted, and a plausible mechanism was proposed. Furthermore, this protocol was applied to concise synthesis of 5-HT3 receptor antagonist in gram-scale.

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Study Snapshot

Rh(III)-catalyzed C-H activation/cyclization of indoles and pyrroles allows for the divergent synthesis of privileged heterocycles, potentially aiding in the synthesis of 5-HT3 receptor antagonists.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Rh(III)-catalyzed C-H activation/cyclization of indoles and pyrroles: divergent synthesis of heterocycles.

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