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Synthesis and Structure of Azacalix[2]pyrimidine[2]triazines and Their Self‐assembly in the Solid State
Author(s) -
Wang Lixia,
Wang Dexian,
Wang Meixiang
Publication year - 2014
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201400505
Subject(s) - chemistry , pyrimidine , cyanuric chloride , triazine , hydrogen bond , intermolecular force , solid state , nucleophile , nucleophilic aromatic substitution , nucleophilic substitution , coupling reaction , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis , molecule
A number of azacalix[2]pyrimidine[2]triazines were synthesized in moderate to good yields from both a step‐wise fragment coupling approach and a one‐pot reaction strategy starting from 4,6‐diaminopyrimidines and cyanuric chloride. Nucleophilic aromatic substitution reaction of resulting dichloro‐substituted azacalix[2]pyrimidine[2]triazines with NH 4 Cl led to the formation of NH 2 ‐bearing azacalix[2]pyrimidine[2]triazine analogs. Azacalix[2]pyrimidine[2]triazines adopted symmetric 1,3‐alternate conformations in solution while twisted 1,3‐alternate conformations were observed in the solid state. In the presence of different additives during the growth of single crystals, azacalix[2]pyrimidine[2]triazines containing amino (‐NH 2 ) groups gave varied self‐assembled structures due to the formation of different intermolecular hydrogen bond motifs.