Synthesis and Characterization of Novel 2,3-Dihydro-3-arylmethylene-4-aryl-1,5-benzo[b]thiazepine

Abstract

In the presence of hydrochloric acid and ethanol, interacotion of acetophenone, paraformaldehyde and N,N-dimethylformamide gave Mannich base. This base reacted with 1,2,4-triazole in water to give propiophenone with 1,2,4-triazole as its inclusion. The propiophenone and benzenecarbaldehyde un-derwent an aldol condensation in the presence of piperidine and toluene to afford a series of chalcone con-taining 1,2,4-triazole. Catalyzed by trifluoroacetic acid, the chalcone and o-aminothiophenol took place nucleophilic substitution reaction, and then occured dehydration to gain a series of 2,3-dihydro-3-arylmethylene-4- aryl-1,5-benzothiazepine, the structures of which were characterized by elemental analysis, IR, ¹H NMR and MS techniques.

Key words: 1,2,4-triazole, 1,5-benzo[b]thiazepine, chalcone

Cite this article

YANG De-Bao^a, YANG Chun^a, XU Feng,b, LIU Fang-Ming*^,a,b,c. Synthesis and Characterization of Novel 2,3-Dihydro-3-arylmethylene-4-aryl-1,5-benzo[b]thiazepine[J]. Chin. J. Org. Chem., 2008, 28(06): 1029-1034.

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型2,3-二氢-3-芳亚甲基-4-芳基-1,5-苯并硫氮杂的合成及表征