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Ruthenium-catalyzed synthesis of isoquinolones with 8-aminoquinoline as a bidentate directing group in C-H functionalization.
J Org Chem. 2014 May 02; 79(9):3963-72.JO

Abstract

Ruthenium-catalyzed oxidative annulation of N-quinolin-8-yl-benzamides with alkynes in open air has been achieved using 8-aminoquinolinyl moiety as a bidentate directing group in the presence of Cu(OAc)2·H2O as an oxidant. This reaction offers a broad substrate scope, and both symmetrical and unsymmetrical alkynes can be applied. High regioselectivity was achieved in the case of unsymmetrical (aryl)alkynes. Reaction with heteroaryl amides was also successful in this catalytic process. A ruthenium-N-quinolin-8-yl-benzamide complex was isolated in the absence of alkyne; in the absence of both N-quinolin-8-yl-benzamide and alkyne, in contrast to literature, only the monoacetate complex RuCl(OAc)(p-cymene), but not the bis-acetate complex Ru(OAc)2(p-cymene), was isolated. These data suggest that this reaction may proceed via N,N-bidentate chelate complex. Key products were characterized by X-ray crystallography.

Authors+Show Affiliations

School of Chemistry, University of Hyderabad , Hyderabad 500 046, Andhra Pradesh, India.No affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

24730396

Citation

Allu, Srinivasarao, and K C Kumara Swamy. "Ruthenium-catalyzed Synthesis of Isoquinolones With 8-aminoquinoline as a Bidentate Directing Group in C-H Functionalization." The Journal of Organic Chemistry, vol. 79, no. 9, 2014, pp. 3963-72.
Allu S, Swamy KC. Ruthenium-catalyzed synthesis of isoquinolones with 8-aminoquinoline as a bidentate directing group in C-H functionalization. J Org Chem. 2014;79(9):3963-72.
Allu, S., & Swamy, K. C. (2014). Ruthenium-catalyzed synthesis of isoquinolones with 8-aminoquinoline as a bidentate directing group in C-H functionalization. The Journal of Organic Chemistry, 79(9), 3963-72. https://doi.org/10.1021/jo500424p
Allu S, Swamy KC. Ruthenium-catalyzed Synthesis of Isoquinolones With 8-aminoquinoline as a Bidentate Directing Group in C-H Functionalization. J Org Chem. 2014 May 2;79(9):3963-72. PubMed PMID: 24730396.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Ruthenium-catalyzed synthesis of isoquinolones with 8-aminoquinoline as a bidentate directing group in C-H functionalization. AU - Allu,Srinivasarao, AU - Swamy,K C Kumara, Y1 - 2014/04/23/ PY - 2014/4/16/entrez PY - 2014/4/16/pubmed PY - 2014/12/15/medline SP - 3963 EP - 72 JF - The Journal of organic chemistry JO - J Org Chem VL - 79 IS - 9 N2 - Ruthenium-catalyzed oxidative annulation of N-quinolin-8-yl-benzamides with alkynes in open air has been achieved using 8-aminoquinolinyl moiety as a bidentate directing group in the presence of Cu(OAc)2·H2O as an oxidant. This reaction offers a broad substrate scope, and both symmetrical and unsymmetrical alkynes can be applied. High regioselectivity was achieved in the case of unsymmetrical (aryl)alkynes. Reaction with heteroaryl amides was also successful in this catalytic process. A ruthenium-N-quinolin-8-yl-benzamide complex was isolated in the absence of alkyne; in the absence of both N-quinolin-8-yl-benzamide and alkyne, in contrast to literature, only the monoacetate complex RuCl(OAc)(p-cymene), but not the bis-acetate complex Ru(OAc)2(p-cymene), was isolated. These data suggest that this reaction may proceed via N,N-bidentate chelate complex. Key products were characterized by X-ray crystallography. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/24730396/Ruthenium_catalyzed_synthesis_of_isoquinolones_with_8_aminoquinoline_as_a_bidentate_directing_group_in_C_H_functionalization_ L2 - https://doi.org/10.1021/jo500424p DB - PRIME DP - Unbound Medicine ER -