Synthesis of 1,3,5‐Trisubstituted 1H‐1,2,4‐Triazoles Containing Hetaryl Fragments.

Abstract

Synthesis of 1,3,5-Trisubstituted 1H-1,2,4-Triazoles Containing Hetaryl Fragments. -(KELAREV, V. I.; SILIN, M. A.; KOBRAKOV, K. I.; RYBINA, I. I.; KOROLEV, V. K.; Chem. Heterocycl. Compd. (N. Y.) 39 (2003) 6, 736-743; Gubkin Oil Gas State Univ., Moscow 117917, Russia; Eng.) -M. Paetzel

Design, Synthesis, Biological Evaluation and Pharmacokinetics of Bis(hydroxyphenyl) substituted Azoles, Thiophenes, Benzenes, and Aza-Benzenes as Potent and Selective Nonsteroidal Inhibitors of 17β-Hydroxysteroid Dehydrogenase Type 1 (17β-HSD1)

“…The synthesis of compounds 12 − 15 is presented in Scheme . The dimethoxylated-1,2,4-triazoles 12i − 15i were synthesized by reaction of the N -acylimidates 12ii − 15ii with methylhydrazine (method D: MeNHNH 2 , CH 2 Cl 2 , 30−40 °C, 4 h). The methoxy groups of compounds 12i − 15i were cleaved with borontrifluoride dimethyl sulfide complex (method F: BF 3 ·SMe 2 , CH 2 Cl 2 , rt, 20 h, Scheme ).…”

The role of the heterocycle in bis(hydroxyphenyl)triazoles for inhibition of 17β-Hydroxysteroid Dehydrogenase (17β-HSD) type 1 and type 2

“…Starting from the Nacylimidates 4b-6b prepared according to the method described by Kelarev et al (Kelarev et al, 2003), the dimethoxylated 1,2,4-triazoles 4a-9a were synthesized by nucleophilic addition of methylhydrazine for compounds 4a-6a and phenylhydrazine for compounds 7a-9a. The deprotection of the methoxy groups of compounds 4a-9a was performed with borontrifluoride dimethyl sulfide complex .…”