Synthesis, Structure and Bioactivity of Some Sulfur‐Containing sym‐Triazine Derivatives.

Mikhailichenko, S. N.; Cheshyuk, A. A.; Suslov, V. I.; Yukhomenko, M. M.; Zaplishnyi, V. N.

doi:10.1002/chin.200303132

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“…With the aim of broadening the series of sym-triazine derivatives [2,11] it was of interest to synthesize iminotriphenylphosphoranes which also contain a pyrrole fragment in their structure. The 4-azido-2-(1H-1-pyrrolyl)-1,3,5-triazines 2i,j were used as starting materials.…”

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confidence: 99%

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

Chesnyuk

Mikhailichenko

Zaplishnyi

et al. 2008

Chem Heterocycl Comp

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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.

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Section: (95)mentioning

confidence: 99%