Синтез трициклічної системи з ядром 7-деазааденіну

• Дата: 2018
• Автори: Muzychka, L. V., Yaremchuk, I. O., Verves, Ye. V., Smolii, O. B.
• Формат: Стаття
• Мова: Ukrainian
• Опубліковано: National University of Pharmacy 2018
• Теми: pyrrolo[2; 3-d]pyrimidine; 7-deazaadenine; iodolactonization; 1-deazapyrimido[1; 2; 3-cd]purine; UDC 547.857 547.859; пирроло[2; 3-d]пиримидин; 7-деазааденин; йодолактонизация; 1-деазапиримидо[1; 3- cd]пурин; УДК 547.857 547.859; піроло[2; 3-d]піримідин; 7-деазааденін; йодолактонізація; 1-деазапіримідо[1; 3-cd]пурин
• Онлайн доступ: https://ophcj.nuph.edu.ua/article/view/ophcj.18.936
• Назва журналу: Journal of Organic and Pharmaceutical Chemistry

Aim. To develop new convenient approaches to the synthesis of new tricyclic compounds with the 7-deazaadenine nucleus as promising synthons for the search of biologically active compounds.Results and discussion. A new simple approach to the synthesis of 4-amino substituted pyrrolo[2,3-d]pyrimidine-6-carboxylic acids was found. A tricyclic derivative of 7-deazadenine was obtained by the intramolecular cyclization of methyl 7-oxiranylmethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylate.Experimental part. Treatment of 4-methoxypyrrolo[2,3-d]pyrimidine with ammonium acetate while heating leads to 4-aminopyrolo[2,3-d]pyrimidine-6-carboxylic acid. This acid reacts with iodine in acetic acid producing 8-iodomethylpyrimido[5’,4’:4,5]pyrrolo[2,1-c][1,4]oxazine with a high yield. Treatment of oxazine with sodium methylate gives 7-(oxiran-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylate; when it is heated with triethylamine hydrochloride in acetonitrile, 10-amino-5,6-dihydro-4H-1-deazapyrimido[1,2,3-cd]purine-2-carboxylate previously unknown is obtained. The structure and composition of the substances obtained were confirmed by NMR-spectroscopy, chromatography mass-spectrometry and elemental analysis.Conclusions. A new convenient approach to the synthesis of 10-amino-5,6-dihydro-4H-1-deazapyrimido[1,2,3-cd]purine-2-carboxylate has been developed. This compound is a tricyclic system with the 7-deazaadenine nucleus. Its further modification may produce potential biologically active substances.