Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 11, Pages 3786-3796Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo100571c
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Funding
- National Natural Science Foundation of China [20772125, 20875094]
- Ministry of Science and Technology [2007CB808055]
- Chinese Academy of Sciences
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A number of homo[2] and homo[4] heterocalix[2]arene[2]triazines were synthesized through a general and good-yielding fragment coupling approach starting from cyanuric halides, aromatic and aliphatic diols, and diamines under very mild reaction conditions. While homo[2] tetraazacalix[2]arene[2]triazine gave a twisted and pinched 1,2-alternate conformer, almost all homo[2] heterocalix[2]arene[2]triazines adopted different partial cone conformations in the solid state. Homo[41] heterocalix[2]arene[2]triazines yielded more diverse conformational structures including partial cone, pinched partial cone, 1,2-alternate and twisted 1.2-alternate, depending on the nature abridging moieties. On the basis of H-1 NMR spectra, homo[2] and homo[4] heterocalix[2]arene[2]triazines were fluxional macrocycles in solution, and they underwent rapid conformation interconversion at different temperatures. Efficient and straightforward nucleophilic aromatic substitution reaction and palladium-catalyzed cross-coupling reactions on chlorotriazine rings, and the nucleophilic alkylation reaction on the bridging nitrogen atoms led to the construction of various highly functionalized homo heterocalix[2]arene[2]triazine derivatives.
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