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Cobalt-Catalyzed Cyclization of N-Methoxy Benzamides with Alkynes using an Internal Oxidant through C-H/N-O Bond Activation.
Chemistry. 2016 Apr 18; 22(17):5899-903.C

Abstract

The cyclization of substituted N-methoxy benzamides with alkynes in the presence of an easily affordable cobalt complex and NaOAc provides isoquinolone derivatives in good to excellent yields. The cyclization reaction is compatible with a range of functional group-substituted benzamides, as well as ester- and alcohol-substituted alkynes. The cobalt complex [Co(III) Cp*(OR)2 ] (R=Me or Ac) serves as an efficient catalyst for the cyclization reaction. Later, isoquinolone derivatives were converted into 1-chloro and 1-bromo substituted isoquinoline derivatives in excellent yields in the presence of POCl3 or PBr3 .

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Publisher Full Text (DOI)

Authors+Show Affiliations

Sivakumar G
Department of Chemistry, Indian Institute of Science Education and Research, Pune, 411021, India.
Vijeta A
Department of Chemistry, Indian Institute of Science Education and Research, Pune, 411021, India.
Jeganmohan M
Department of Chemistry, Indian Institute of Science Education and Research, Pune, 411021, India. mjeganmohan@iiserpune.ac.in.

Pub Type(s)

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

Language

eng

PubMed ID

26951887

Citation

Sivakumar, Ganesan, et al. "Cobalt-Catalyzed Cyclization of N-Methoxy Benzamides With Alkynes Using an Internal Oxidant Through C-H/N-O Bond Activation." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 22, no. 17, 2016, pp. 5899-903.
Sivakumar G, Vijeta A, Jeganmohan M. Cobalt-Catalyzed Cyclization of N-Methoxy Benzamides with Alkynes using an Internal Oxidant through C-H/N-O Bond Activation. Chemistry. 2016;22(17):5899-903.
Sivakumar, G., Vijeta, A., & Jeganmohan, M. (2016). Cobalt-Catalyzed Cyclization of N-Methoxy Benzamides with Alkynes using an Internal Oxidant through C-H/N-O Bond Activation. Chemistry (Weinheim an Der Bergstrasse, Germany), 22(17), 5899-903. https://doi.org/10.1002/chem.201600471
Sivakumar G, Vijeta A, Jeganmohan M. Cobalt-Catalyzed Cyclization of N-Methoxy Benzamides With Alkynes Using an Internal Oxidant Through C-H/N-O Bond Activation. Chemistry. 2016 Apr 18;22(17):5899-903. PubMed PMID: 26951887.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Cobalt-Catalyzed Cyclization of N-Methoxy Benzamides with Alkynes using an Internal Oxidant through C-H/N-O Bond Activation. AU - Sivakumar,Ganesan, AU - Vijeta,Arjun, AU - Jeganmohan,Masilamani, Y1 - 2016/03/16/ PY - 2016/02/01/received PY - 2016/3/9/entrez PY - 2016/3/10/pubmed PY - 2016/3/10/medline KW - C−H activation KW - annulation KW - cobalt KW - heterocycles KW - homogeneous catalysis SP - 5899 EP - 903 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 22 IS - 17 N2 - The cyclization of substituted N-methoxy benzamides with alkynes in the presence of an easily affordable cobalt complex and NaOAc provides isoquinolone derivatives in good to excellent yields. The cyclization reaction is compatible with a range of functional group-substituted benzamides, as well as ester- and alcohol-substituted alkynes. The cobalt complex [Co(III) Cp*(OR)2 ] (R=Me or Ac) serves as an efficient catalyst for the cyclization reaction. Later, isoquinolone derivatives were converted into 1-chloro and 1-bromo substituted isoquinoline derivatives in excellent yields in the presence of POCl3 or PBr3 . SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/26951887/Cobalt_Catalyzed_Cyclization_of_N_Methoxy_Benzamides_with_Alkynes_using_an_Internal_Oxidant_through_C_H/N_O_Bond_Activation_ DB - PRIME DP - Unbound Medicine ER -