ICI-195739
(2R)-2-(2,4-二氟苯基)-1-[3-[(Z)-2-[4-(2,2,3,3-四氟丙氧基)苯基]乙烯基]-1,2,4-三唑-1-基]-3-(1,2,4-三唑-1-基)丙-2-醇Chemical Name: 2-(2,4-Difluorophenyl)-1-[3-[2-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]vinyl]-1,2,4-triazol-1-yl]-3-(1,2,4-triazol-1-yl)propan-2-ol
CAS No. 103961-78-0
项目整合开发状态: Preclinical
项目研究机构: AstraZeneca (Originator)
合成路线:The condensation of 4-(2,2,3,3-tetrafluoropropoxy)benzaldehyde (I) with refluxing acetic anhydride gives 3-[4-(2,2,3,3-tetrafluoropropoxy) phenyl]acrylic acid (II),which is treated with refluxing SOCl2 to yield the corresponding acid chloride (III).The reaction of (III) with thiosemicarbazide in toluene affords 3-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]acryloylthiosemicarbazide (IV),which is cyclized by means of NaNO2 and HNO3 in water to give 3-[4-(2,2,3,3-tetrafluoropropoxy) styryl]-1,2,4-triazole (V).Finally,this compound is condensed with 2-(2,4-difluorophenyl)-3-(1,2,4-triazol-1-yl)-1,2-epoxypropane (VI) by means of NaH in hot DMF.
📌 参考资料/链接：
参考文献标题:Antifungal azole cpds.
文献作者:Bayles,F.T.; Boyle,F.T.; Gravestock,M.B.; Wardleworth,J.M.(AstraZeneca plc)
参考来源:EP 0174769; US 4925863
📄 详细内容
合成路线:The condensation of 4-(2,2,3,3-tetrafluoropropoxy)benzaldehyde (I) with refluxing acetic anhydride gives 3-[4-(2,2,3,3-tetrafluoropropoxy) phenyl]acrylic acid (II),which is treated with refluxing SOCl2 to yield the corresponding acid chloride (III).The reaction of (III) with thiosemicarbazide in toluene affords 3-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]acryloylthiosemicarbazide (IV),which is cyclized by means of NaNO2 and HNO3 in water to give 3-[4-(2,2,3,3-tetrafluoropropoxy) styryl]-1,2,4-triazole (V).Finally,this compound is condensed with 2-(2,4-difluorophenyl)-3-(1,2,4-triazol-1-yl)-1,2-epoxypropane (VI) by means of NaH in hot DMF.
参考文献标题:ICI-195739
文献作者:Prous,J.; Castar,J.
参考来源:Drugs Fut 1988,13(5),408
产品链接: CAS No. 103961-78-0››