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Rh(III)-catalyzed C-H activation/cyclization of indoles and pyrroles: divergent synthesis of heterocycles.
J Org Chem. 2014 Jul 18; 79(14):6490-500.JO

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.

Authors+Show Affiliations

Institute of Materia Medica and College of Pharmaceutical Sciences, Zhejiang University , Hangzhou 310058, China.No affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

24949803

Citation

Zhang, Yan, et al. "Rh(III)-catalyzed C-H Activation/cyclization of Indoles and Pyrroles: Divergent Synthesis of Heterocycles." The Journal of Organic Chemistry, vol. 79, no. 14, 2014, pp. 6490-500.
Zhang Y, Zheng J, Cui S. Rh(III)-catalyzed C-H activation/cyclization of indoles and pyrroles: divergent synthesis of heterocycles. J Org Chem. 2014;79(14):6490-500.
Zhang, Y., Zheng, J., & Cui, S. (2014). Rh(III)-catalyzed C-H activation/cyclization of indoles and pyrroles: divergent synthesis of heterocycles. The Journal of Organic Chemistry, 79(14), 6490-500. https://doi.org/10.1021/jo500902n
Zhang Y, Zheng J, Cui S. Rh(III)-catalyzed C-H Activation/cyclization of Indoles and Pyrroles: Divergent Synthesis of Heterocycles. J Org Chem. 2014 Jul 18;79(14):6490-500. PubMed PMID: 24949803.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rh(III)-catalyzed C-H activation/cyclization of indoles and pyrroles: divergent synthesis of heterocycles. AU - Zhang,Yan, AU - Zheng,Jing, AU - Cui,Sunliang, Y1 - 2014/06/26/ PY - 2014/6/21/entrez PY - 2014/6/21/pubmed PY - 2014/12/15/medline SP - 6490 EP - 500 JF - The Journal of organic chemistry JO - J Org Chem VL - 79 IS - 14 N2 - 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. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/24949803/Rh_III__catalyzed_C_H_activation/cyclization_of_indoles_and_pyrroles:_divergent_synthesis_of_heterocycles_ L2 - https://doi.org/10.1021/jo500902n DB - PRIME DP - Unbound Medicine ER -