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Palladium-catalyzed Sonogashira-coupling conjoined C-H activation: a regioselective tandem strategy to access indolo- and pyrrolo[1,2-a]quinolines.
J Org Chem. 2012 Nov 16; 77(22):10382-92.JO

Abstract

An operationally simple approach for the regioselective tandem synthesis of indolo[1,2-a]quinolines 4a-v and pyrrolo[1,2-a]quinolines 5a-k from 1-(2-bromophenyl)-1H-indole/pyrrole/imidazole 1a-c, 2a,b by the palladium-catalyzed sequential C-C bond formation is described. The developed approach involves the palladium-catalyzed Sonogashira coupling followed by the intramolecular C-C bond formation via C-H activation, which leads to the formation of 6-endo-dig cyclized product. This synthetic methodology accommodates wide functional group variation on alkyne, which proves to be advantageous for the structural and biological activity assessments.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Shukla SP
Synthetic Organic Chemistry Research Laboratory, Department of Chemistry, University of Delhi, Delhi, 110007, India.
Tiwari RK
No affiliation info available
Verma AK
No affiliation info available

MeSH

AlkynesCatalysisCyclizationHydrogen BondingImidazolesIndolesMolecular StructurePalladiumPyrrolesQuinolinesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

23083404

Citation

Shukla, Satya Prakash, et al. "Palladium-catalyzed Sonogashira-coupling Conjoined C-H Activation: a Regioselective Tandem Strategy to Access Indolo- and Pyrrolo[1,2-a]quinolines." The Journal of Organic Chemistry, vol. 77, no. 22, 2012, pp. 10382-92.
Shukla SP, Tiwari RK, Verma AK. Palladium-catalyzed Sonogashira-coupling conjoined C-H activation: a regioselective tandem strategy to access indolo- and pyrrolo[1,2-a]quinolines. J Org Chem. 2012;77(22):10382-92.
Shukla, S. P., Tiwari, R. K., & Verma, A. K. (2012). Palladium-catalyzed Sonogashira-coupling conjoined C-H activation: a regioselective tandem strategy to access indolo- and pyrrolo[1,2-a]quinolines. The Journal of Organic Chemistry, 77(22), 10382-92. https://doi.org/10.1021/jo302112a
Shukla SP, Tiwari RK, Verma AK. Palladium-catalyzed Sonogashira-coupling Conjoined C-H Activation: a Regioselective Tandem Strategy to Access Indolo- and Pyrrolo[1,2-a]quinolines. J Org Chem. 2012 Nov 16;77(22):10382-92. PubMed PMID: 23083404.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium-catalyzed Sonogashira-coupling conjoined C-H activation: a regioselective tandem strategy to access indolo- and pyrrolo[1,2-a]quinolines. AU - Shukla,Satya Prakash, AU - Tiwari,Rakesh K, AU - Verma,Akhilesh K, Y1 - 2012/10/30/ PY - 2012/10/23/entrez PY - 2012/10/23/pubmed PY - 2013/5/11/medline SP - 10382 EP - 92 JF - The Journal of organic chemistry JO - J Org Chem VL - 77 IS - 22 N2 - An operationally simple approach for the regioselective tandem synthesis of indolo[1,2-a]quinolines 4a-v and pyrrolo[1,2-a]quinolines 5a-k from 1-(2-bromophenyl)-1H-indole/pyrrole/imidazole 1a-c, 2a,b by the palladium-catalyzed sequential C-C bond formation is described. The developed approach involves the palladium-catalyzed Sonogashira coupling followed by the intramolecular C-C bond formation via C-H activation, which leads to the formation of 6-endo-dig cyclized product. This synthetic methodology accommodates wide functional group variation on alkyne, which proves to be advantageous for the structural and biological activity assessments. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/23083404/Palladium_catalyzed_Sonogashira_coupling_conjoined_C_H_activation:_a_regioselective_tandem_strategy_to_access_indolo__and_pyrrolo[12_a]quinolines_ L2 - https://doi.org/10.1021/jo302112a DB - PRIME DP - Unbound Medicine ER -