DIOXOTHIETANYLATION OF HETEROCYCLES 2*. IMIDAZOLES AND BENZIMIDAZOLES

Authors

  • Надежда Н. Макарова Bashkir State Medical University, 3 Lenina St., Ufa 450008, Russia
  • Елена Э. Клен Bashkir State Medical University, 3 Lenina St., Ufa 450008, Russia
  • Феркат А. Халиуллин Bashkir State Medical University, 3 Lenina St., Ufa 450008, Russia

DOI:

https://doi.org/10.1007/4943

Keywords:

benzimidazole, imidazole, thietane 1, 1-dioxide, 1, 2, 4-triazole, aza-Michael reaction, dioxothietanylation

Abstract

1-(1,1-Dioxidothietan-3-yl)-1H-imidazoles and 1-(1,1-dioxidothietan-3-yl)-1H-benzimidazoles were synthesized in the reaction of 3,5-dibromo-1-(1,1-dioxidothietan-3-yl)-1H-1,2,4-triazole with the sodium salts of imidazoles and benzimidazoles. The reaction involves addition of azoles to thiete 1,1-dioxide formed in situ, which acts as a Michael acceptor. The effect of pKa values of imidazoles and benzimidazoles on their reactivity is shown.

Author Biographies

Надежда Н. Макарова, Bashkir State Medical University, 3 Lenina St., Ufa 450008, Russia

синтез новых производных азотсодержащих гетероциклов, кафедра фармацевтической химии, доцент

Елена Э. Клен, Bashkir State Medical University, 3 Lenina St., Ufa 450008, Russia

синтез новых производных азотсодержащих гетероциклов, кафедра фармацевтической химии, профессор

Феркат А. Халиуллин, Bashkir State Medical University, 3 Lenina St., Ufa 450008, Russia

синтез новых производных азотсодержащих гетероциклов, кафедра фармацевтической химии, профессор

Published

2019-09-17

Issue

Section

Original Papers