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Expedient synthesis of pyrroloquinolinones by Rh-catalyzed annulation of N-carbamoyl indolines with alkynes through a directed C-H functionalization/C-N cleavage sequence.
Org Lett. 2015 Mar 20; 17(6):1481-4.OL

Abstract

A Rh-catalyzed redox-neutral C-H functionalization of N-carbamoyl indolines with various internal alkynes has been developed. The reaction, which involves the sequential cleavage of the C-H bond of the indoline at the C7-position and the C-N bond of the urea motif, provides a divergent protocol to rapidly assemble fused-ring pyrroloquinolinone analogues by using a direct alkenylation/annulation strategy with high efficiency and selectivity.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Yang XF
‡Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.
Hu XH
‡Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.
Loh TP
†Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China. ‡Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.

MeSH

AlkynesCatalysisCyclizationHeterocyclic Compounds, 3-RingIndole AlkaloidsMolecular StructureOxidation-ReductionRhodium

Pub Type(s)

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

Language

eng

PubMed ID

25754346

Citation

Yang, Xiao-Fei, et al. "Expedient Synthesis of Pyrroloquinolinones By Rh-catalyzed Annulation of N-carbamoyl Indolines With Alkynes Through a Directed C-H functionalization/C-N Cleavage Sequence." Organic Letters, vol. 17, no. 6, 2015, pp. 1481-4.
Yang XF, Hu XH, Loh TP. Expedient synthesis of pyrroloquinolinones by Rh-catalyzed annulation of N-carbamoyl indolines with alkynes through a directed C-H functionalization/C-N cleavage sequence. Org Lett. 2015;17(6):1481-4.
Yang, X. F., Hu, X. H., & Loh, T. P. (2015). Expedient synthesis of pyrroloquinolinones by Rh-catalyzed annulation of N-carbamoyl indolines with alkynes through a directed C-H functionalization/C-N cleavage sequence. Organic Letters, 17(6), 1481-4. https://doi.org/10.1021/acs.orglett.5b00355
Yang XF, Hu XH, Loh TP. Expedient Synthesis of Pyrroloquinolinones By Rh-catalyzed Annulation of N-carbamoyl Indolines With Alkynes Through a Directed C-H functionalization/C-N Cleavage Sequence. Org Lett. 2015 Mar 20;17(6):1481-4. PubMed PMID: 25754346.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Expedient synthesis of pyrroloquinolinones by Rh-catalyzed annulation of N-carbamoyl indolines with alkynes through a directed C-H functionalization/C-N cleavage sequence. AU - Yang,Xiao-Fei, AU - Hu,Xu-Hong, AU - Loh,Teck-Peng, Y1 - 2015/03/10/ PY - 2015/3/11/entrez PY - 2015/3/11/pubmed PY - 2015/8/22/medline SP - 1481 EP - 4 JF - Organic letters JO - Org Lett VL - 17 IS - 6 N2 - A Rh-catalyzed redox-neutral C-H functionalization of N-carbamoyl indolines with various internal alkynes has been developed. The reaction, which involves the sequential cleavage of the C-H bond of the indoline at the C7-position and the C-N bond of the urea motif, provides a divergent protocol to rapidly assemble fused-ring pyrroloquinolinone analogues by using a direct alkenylation/annulation strategy with high efficiency and selectivity. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/25754346/Expedient_synthesis_of_pyrroloquinolinones_by_Rh_catalyzed_annulation_of_N_carbamoyl_indolines_with_alkynes_through_a_directed_C_H_functionalization/C_N_cleavage_sequence_ DB - PRIME DP - Unbound Medicine ER -