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Synthesis of azaheterocycles from aryl ketone O-acetyl oximes and internal alkynes by Cu-Rh bimetallic relay catalysts.
J Org Chem. 2011 Aug 05; 76(15):6159-68.JO

Abstract

A synthetic method for azaheterocycles from aryl ketone O-acetyl oximes and internal alkynes has been developed by using the Cu(OAc)(2)-[Cp*RhCl(2)](2) bimetallic catalytic system. The reactions proceeded with both of anti- and syn-isomers of oximes with a wide scope of substituents. The Cu-Rh bimetallic system could be applied for the synthesis of isoquinolines as well as β-carboline, furo[2.3-c]pyridine, pyrrolo[2,3-c]pyridine, and thieno[2,3-c]pyridine derivatives.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Too PC
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.
Chua SH
No affiliation info available
Wong SH
No affiliation info available
Chiba S
No affiliation info available

MeSH

AlkynesCarbolinesCatalysisCopperHeterocyclic CompoundsIsoquinolinesKetonesMolecular StructureOrganometallic CompoundsOximesPyrimidinesRhodium

Pub Type(s)

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

Language

eng

PubMed ID

21688786

Citation

Too, Pei Chui, et al. "Synthesis of Azaheterocycles From Aryl Ketone O-acetyl Oximes and Internal Alkynes By Cu-Rh Bimetallic Relay Catalysts." The Journal of Organic Chemistry, vol. 76, no. 15, 2011, pp. 6159-68.
Too PC, Chua SH, Wong SH, et al. Synthesis of azaheterocycles from aryl ketone O-acetyl oximes and internal alkynes by Cu-Rh bimetallic relay catalysts. J Org Chem. 2011;76(15):6159-68.
Too, P. C., Chua, S. H., Wong, S. H., & Chiba, S. (2011). Synthesis of azaheterocycles from aryl ketone O-acetyl oximes and internal alkynes by Cu-Rh bimetallic relay catalysts. The Journal of Organic Chemistry, 76(15), 6159-68. https://doi.org/10.1021/jo200897q
Too PC, et al. Synthesis of Azaheterocycles From Aryl Ketone O-acetyl Oximes and Internal Alkynes By Cu-Rh Bimetallic Relay Catalysts. J Org Chem. 2011 Aug 5;76(15):6159-68. PubMed PMID: 21688786.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of azaheterocycles from aryl ketone O-acetyl oximes and internal alkynes by Cu-Rh bimetallic relay catalysts. AU - Too,Pei Chui, AU - Chua,Sze Hui, AU - Wong,Siong Heng, AU - Chiba,Shunsuke, Y1 - 2011/06/29/ PY - 2011/6/22/entrez PY - 2011/6/22/pubmed PY - 2012/1/18/medline SP - 6159 EP - 68 JF - The Journal of organic chemistry JO - J Org Chem VL - 76 IS - 15 N2 - A synthetic method for azaheterocycles from aryl ketone O-acetyl oximes and internal alkynes has been developed by using the Cu(OAc)(2)-[Cp*RhCl(2)](2) bimetallic catalytic system. The reactions proceeded with both of anti- and syn-isomers of oximes with a wide scope of substituents. The Cu-Rh bimetallic system could be applied for the synthesis of isoquinolines as well as β-carboline, furo[2.3-c]pyridine, pyrrolo[2,3-c]pyridine, and thieno[2,3-c]pyridine derivatives. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/21688786/Synthesis_of_azaheterocycles_from_aryl_ketone_O_acetyl_oximes_and_internal_alkynes_by_Cu_Rh_bimetallic_relay_catalysts_ DB - PRIME DP - Unbound Medicine ER -