L-PROLINE AND RELATED CHIRAL HETEROCYCLIC AMINO ACIDS AS SCAFFOLDS FOR THE SYNTHESIS OF FUNCTIONALIZED 2-AMINO-1,3-SELENAZOLE-5-CARBOXYLATES

Authors

  • Vida Malinauskiene Kaunas University of Technology, Institute of Synthetic Chemistry / Department Organic Chemistry
  • Aiste Kveselyte Kaunas Univeristy of Technology, Institute of Synthetic Chemistry
  • Karolina Dzedulionyte Kaunas University of Technology, Institute of Synthetic Chemistry
  • Aurimas Bieliauskas Kaunas University of Technology, Institute of Synthetic Chemistry
  • Frank Abildgaard Slok Vipergen ApS, company
  • Algirdas Sackus Kaunas University of Technology, Institute of Synthetic Chemistry / Department of Organic Chemistry

DOI:

https://doi.org/10.1007/4376

Keywords:

2-amino-1, 3-selenazole, N-bromosuccinimide, heterocyclic amino acids, β-keto esters, L-proline.

Abstract

A series of methyl 2-amino-1,3-selenazole-5-carboxylates possessing a chiral pyrrolidin-2-yl, piperidin-2-yl, or piperidin-3-yl substituent at the C-4 atom of the heteroaromatic ring was designed and synthesized. In the first stage of the synthesis, the carboxylic acid functional group of the L-proline or related chiral heterocyclic amino acid was converted to the corresponding β-keto ester, which was then α-brominated with N-bromosuccinimide. The subsequent reaction of the α-brominated β-keto ester with selenourea afforded the target
methyl 2-amino-1,3-selenazole-5-carboxylate. The structures of the novel heterocyclic compounds were confirmed by 1H, 13C, and 77Se NMR spectroscopy and HRMS.

Author Biographies

Vida Malinauskiene, Kaunas University of Technology, Institute of Synthetic Chemistry / Department Organic Chemistry

Research Associate

Aiste Kveselyte, Kaunas Univeristy of Technology, Institute of Synthetic Chemistry

Researcher

Karolina Dzedulionyte, Kaunas University of Technology, Institute of Synthetic Chemistry

Researcher

Aurimas Bieliauskas, Kaunas University of Technology, Institute of Synthetic Chemistry

PhD student

Frank Abildgaard Slok, Vipergen ApS, company

PhD, Head of Chemistry

Algirdas Sackus, Kaunas University of Technology, Institute of Synthetic Chemistry / Department of Organic Chemistry

Director / Professor

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Published

2018-06-04

Issue

Vol. 54 No. 4 (2018): Stereoselective synthesis of heterocyclic compounds

Section

Original Papers