Synthesis of 1,2,3,4-tetrahydropyrido- [2,3-b]pyrazine-2,3-dione derivatives with a chiral substituent at the nitrogen atom Article

Kurkin, AV, Bukhryakov, KV, Yurovskaya, MA. (2009). Synthesis of 1,2,3,4-tetrahydropyrido- [2,3-b]pyrazine-2,3-dione derivatives with a chiral substituent at the nitrogen atom . 45(2), 188-193. 10.1007/s10593-009-0249-z

cited authors

  • Kurkin, AV; Bukhryakov, KV; Yurovskaya, MA

authors

abstract

  • The sequence of steps including nucleophilic substitution of the chlorine atom in 2-chloro-3-nitropyridine by esters of optically active phenylalanine, reduction of the nitro group, acylation with ethyl oxalyl chloride, and intramolecular cyclization, leads to the synthesis of derivatives of 1,2,3,4-tetrahydropyrido[2,3-b]pyrazine-2,3-dione with a chiral substituent at the nitrogen atom. It was established that, depending on the conditions of carrying out the cyclization, the parallel formation of derivatives of imidazo[4,5-b]pyridine is possible. Conditions were found for selectively carrying out the cyclization under with only structures of pyrazines or imidazole condensed with pyridine were formed. © 2009 Springer Science+Business Media, Inc.

publication date

  • February 1, 2009

Digital Object Identifier (DOI)

start page

  • 188

end page

  • 193

volume

  • 45

issue

  • 2