Thiacalix[4]arene bi-benzaldehyde derivative 2 was synthesized by introducing benzaldehyde groups on 1,3-position of p-tert-butylthiacalix[4]arene. Reacting compound 2 with aniline, salicylic hydrazide, nicotinic hydrazide or isonicotinic hydrazide gave series of novel thiacalix[4]arene aza derivatives 3a～3d by the Schiff-base condensation in the yields of 83%, 80%, 77% and 79%, respectively. Treatment compound 2 with o-phenylendiamine, oxalyl dihydrazide, malonic dihydrazide and adipic dihydrazide afforded novel bridged thiacalix[4]arene aza derivatives 4a～4d by “1＋1” condensation in the yields of 53%, 51%, 59% and 66%. The structures of all new compounds were characterized by IR, ESI-MS, ¹H NMR spectra and elemental analyses.

Key words: hydrazide, Schiff-base, synthesis, thiacalix[4]arene