sym-triazines. 8. Synthesis and some reactions of 4,6-disubstituted 2-(1H-pyrrolyl)-1,3,5-triazines

Abstract

We have studied the reaction of 2,5-dimethoxytetrahydrofuran with 4,6-disubstituted 2-amino-1,3,5-triazines with the aim of obtaining novel coupled polyheterocyclic systems with potential bioactivity. Reaction conditions were optimized. A series of novel 4,6-disubstituted 2-(1H-1-pyrrolyl)-sym-triazines was obtained. It was found that the product yields depended on the nature of the substituent in the 4 and 6 positions of the triazine ring and on the reaction conditions. Keywords: 4,6-disubstituted 2-amino-1,3,5-triazines, 2,5-dimethoxytetrahydrofuran, 4-substituted 2-amino-(1,3,5-triazinyl)-6-iminotriphenylphosphoranes, 4-substituted 2-(1H-1-pyrrolyl)-6-(1,2,3-triazol-1-yl)-1,3,5-triazines.In continuing our study of the synthesis of conjugated heterocyclic systems it seemed reasonable to prepare novel compounds containing 1,3,5-triazine, pyrrole, and 1,2,3-triazole rings together. We have previously reported the synthesis of sym-triazine derivatives containing 1,2,3-triazole fragments [2, 3]. The aim of this work is the targeted synthesis of novel and potentially bioactive 4,6-disubstituted 2-(1H-1-pyrrolyl)-1,3,5-triazine derivatives and to study their properties and reactions.It is known [4] that 4,6-dichloro-2-(N-pyrrolyl)-1,3,5-traizines are formed in about 37% yield as a result of the reaction of 2,4,6-trichloro-1,3,5-triazine with pyrrole or pyrrolyl potassium (lithium) in the presence of AlCl 3 . However, this method is only suitable for the substitution of the first chlorine in cyanuric chloride.In [5] it was reported that the primary amino group of alkyl and arylamines can be used as the nitrogen component in the construction of a pyrrole ring via reaction with 2,5-dimethoxytetrahydrofuran. The latter can be used as a latent 1,4-dicarbonyl compound giving high yields of the corresponding N-alkyl-or N-arylpyrroles.

Synthesis and structure of new 1,2,3-triazolyl substituted 1,3,5-triazines

“…Compounds 3d, 3g, 4b, and 5a-c displayed the maximum intensity of the molecular ions. The fragmentation patterns of the molecular ions under electron impact were found to be the same as it was observed for the earlier synthesized heterocyclic derivatives of the 1,3,5-triazine [8,11,25].…”