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A stepwise fragment coupling reaction starting with substituted dichlorotriazine and resorcinol derivatives gave rise to thermodynamicallyfavored 1,3-alternate tetraoxacalix[2]arene[2]triazines and kinetically controlled flattened partial cone tetraoxacalix[2]arene[2]triazines. The flattenedpartial cone conformer, which was stable due to the steric effect, converted into the 1,3-alternate conformer via ether bond cleavage upontreatment with an inorganic base.