SYNTHESIS OF 1,2,3,4-TETRAHYDROPYRIDO [2,3-<i>b</i>]PYRAZINE-2,3-DIONE DERIVATIVES WITH A CHIRAL SUBSTITUENT AT THE NITROGEN ATOM
DOI:
https://doi.org/10.1007/6821Keywords:
трет-бутиловый эфир имидазо[4, 5-b]пиридин-2-карбоновой кислоты, 3-нитро-2-хлорпиридин, 1, 2, 3, 4-тетрагидропиридо[2, 3-b]пиразин-2.3-дионы, хиральный заместитель при атоме азота, эфиры оптически активного фенилаланина, нуклеофильное замещениеAbstract
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.
How to Cite
Kurkin, A. V.; Bukhryakov, K. V.; Yurovskaya, M. A.Chem. Heterocycl. Compd. 2009, 45, 188. [Khim. Geterotsikl. Soedin. 2009, 237.]
For this article in the English edition see DOI 10.1007/s10593-009-0249-z
