有机化学 ›› 2005, Vol. 25 ›› Issue (9): 1089-1093. 上一篇    下一篇

研究论文

微波促进下3-(2-苯并呋喃基)-4-氨基-5-巯基-1,2,4-三唑

王喜存*,权正军,李政   

  1. (西北师范大学化学化工学院 甘肃省高分子材料重点实验室 兰州 730070)
  • 收稿日期:2004-09-22 修回日期:2005-04-05 发布日期:2005-08-24
  • 通讯作者: 王喜存

Microwave-assisted Synthesis of 4-Amino-3- [2-benzo(b)furyl]-5- mercapto-1,2,4-triazole and Its Derivatives

WANG Xi-Cun*,QUAN Zheng-Jun,LI Zheng   

  1. (Gansu Key Laboratory of Polymer Materials, College of Chemistry and Chemical Engineering,
    Northwest Normal University, Lanzhou, Gansu 730070)
  • Received:2004-09-22 Revised:2005-04-05 Published:2005-08-24
  • Contact: WANG Xi-Cun

微波辐射条件下, 首先由2-苯并呋喃甲酰肼依次与二硫化碳和水合肼反应合成3-(2-苯并呋喃基)-4-氨基-5-巯基- 1,2,4-三唑, 进一步在微波辐射条件下由4-氨基-5-巯基-1,2,4-三唑分别与芳甲酸/芳氧基乙酸、α-溴代苯乙酮及芳醛反应以较高产率制得了相应的1,2,4-三唑并[3,4-b]-1,3,4-噻二唑、1,2,4-三唑并[3,4-b]-1,3,4-噻二嗪及4-芳亚甲基亚胺基-5-巯基-1,2,4-三唑. 产物结构经IR, 1H NMR, MS及元素分析进行了表征.

关键词: 合成, 4-芳亚甲基亚胺基-5-巯基-1,2,4-三唑, 微波辐射, 1,2,4-三唑并[3,4-b]-1,3,4-噻二唑, 1,2,4-三唑并[3,4-b]-1,3,4-噻二嗪

4-Amino-3-[2-benzo(b)furyl]-5-mercapto-1,2,4-triazole was synthesized by the reactions of 2-benzo(b)furoyl hydrazine with CS2 and next hydrazine under microwave irradiation. Treatment of the resulting 4-amino-5-mercapto-1,2,4-triazole with aromatic carboxylic acids (or aryloxyacetic acids), α-bromoacetophenones and aromatic aldehydes under microwave irradiation yielded the corresponding 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles, 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines and 4-arylideneamino-5- mercapto-1,2,4-triazole in good to moderate yields, respectively. The structures of all these new compounds were confirmed by elemental analyses, IR, 1H NMR and MS spectra.

Key words: microwave irradiation, 4-arylideneamino-5-mercapto-1,2,4-triazole, 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole, 1,2,4-triazolo[3,4-b]-1,3,4- thiadiazine, synthesis