A new class of 4-[(5-aryl-1,3,4-thiadiazol-2-ylamino)methyl]phenol compounds were synthesized via the nucleophilic addition reaction of 5-phenyl-1,3,4-thiadiazol-2-amine with 4-hydroxybenzaldehyde, dehydration and reduction of unsaturated double bond in one-pot. This procedure has the advantages of short reaction time and simple post treatment. The structures of the products were characterized thoroughly by NMR, IR, MS techniques and elemental analysis.
Chiral N-tert-butanesulfinyl imines have been shown to be important intermediates for asymmetric synthesis in recent years. Eleven new (R,E)-N-(2-hydroxybenzylidene)-tert-butyl-sulfinamides (3) were synthesized from salicylaldehydes 1 and chiral tert-butanesulfinamide 2 under microwave irradiation in moderate to good yields. The reaction could work well in the mixture of KHSO 4 /PhMe or Cs 2 CO 3 /CH 2 Cl 2 . And the results show that the KHSO 4 /PhMe reaction system is helpful for the salicylaldehydes with electron-donating group; however, the Cs 2 CO 3 /CH 2 Cl 2 reaction system is applicable to the salicylaldehydes with electron-deficient group and steric hindrance group. The structures of these new compounds were determined by 1 H NMR, 13 C NMR, IR and HRMS.
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