Volume 2015, Issue 1 pp. 135-141
Full Paper

Synthesis of Tetrasubstituted Symmetrical Pyrazines from β-Keto γ-Amino Esters: A Mild Strategy for Self-Dimerization of Peptides

Mothukuri Ganesh Kumar

Mothukuri Ganesh Kumar

Department of Chemistry, Indian Institute of Science Education and Research, Dr. Homi Bhabha Road, Pune-411 008, India, http://www.iiserpune.ac.in

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Varsha J. Thombare

Varsha J. Thombare

Department of Chemistry, Indian Institute of Science Education and Research, Dr. Homi Bhabha Road, Pune-411 008, India, http://www.iiserpune.ac.in

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Rupal D. Bhaisare

Rupal D. Bhaisare

Department of Chemistry, Indian Institute of Science Education and Research, Dr. Homi Bhabha Road, Pune-411 008, India, http://www.iiserpune.ac.in

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Anindita Adak

Anindita Adak

Department of Chemistry, Indian Institute of Science Education and Research, Dr. Homi Bhabha Road, Pune-411 008, India, http://www.iiserpune.ac.in

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Hosahudya N. Gopi

Corresponding Author

Hosahudya N. Gopi

Department of Chemistry, Indian Institute of Science Education and Research, Dr. Homi Bhabha Road, Pune-411 008, India, http://www.iiserpune.ac.in

Department of Chemistry, Indian Institute of Science Education and Research, Dr. Homi Bhabha Road, Pune-411 008, IndiaSearch for more papers by this author
First published: 25 November 2014
Citations: 3

Graphical Abstract

A facile synthesis of highly symmetrical tetrasubstituted pyrazines through simple aerial oxidation of β-keto γ-esters derived from amino acids and peptides is reported.

Abstract

A facile synthesis of highly symmetrical tetrasubstituted pyrazines through simple aerial oxidation of β-keto γ-amino esters is reported. The scope of the reaction was examined by use of various amino acid side-chain functional groups and peptides. The mild and efficient transformation of β-keto γ-amino esters into pyrazines may serve as an attractive strategy for self-dimerization of peptides.