REACTIONS OF THIIRANES WITH NH-HETEROCYCLES. 1. AN INVESTIGATION OF THE REACTION OF 2-CHLOROMETHYLTHIIRANE WITH 3,5-DIBROMO-4-NITROPYRAZOLE

Authors

  • Феркат А. Халиуллин Bashkir State Medical University,3 Lenina St., Ufa 450008
  • Елена Э. Клен Bashkir State Medical University,3 Lenina St., Ufa 450008
  • Надежда Н. Макарова Bashkir State Medical University,3 Lenina St., Ufa 450008
  • Светлана О. Шепилова Bashkir State Medical University,3 Lenina St., Ufa 450008
  • Ирина П. Байкова Institute of Organic Chemistry, Ufa Scientific Center of the Russian Academy of Sciences, 71 Oktyabrya Ave., Ufa 450054

DOI:

https://doi.org/10.1007/5657

Keywords:

2, 3-dihydropyrazolo[5, 1-b]thiazole, pyrazole, thietane, thiirane, alkylation, thiirane-thietane rearrangement

Abstract

The reaction of 2-chloromethylthiirane with 3,5-dibromo-4-nitropyrazole in H2O and the aprotic solvent MeCN in the presence of bases was investigated. It was found that thiirane-thietane rearrangement occurs in an aqueous medium with the formation of 3,5-dibromo-4-nitro-1-(thietan-3-yl)-1H-pyrazole. In MeCN, 3,5-dibromo-4-nitro-1-(thiiran-2-ylmethyl)-1H-pyrazole and the product of its reaction with the starting pyrazole, 6-bromo-2-[(3,5-dibromo-4-nitro-1H-pyrazol-1-yl)methyl]-7-nitro-2,3-dihydropyrazolo[5,1-b]thiazole, are formed, the yields of which depend on the molar ratio of the reactants.

Authors: Ferkat А. Khaliullin, Elena E. Klen*, Nadezhda N. Makarova, Svetlana O. Shepilova, Irina P. Baikova

Author Biographies

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

Заведующий кафедрой фармацевтической химии с курсами аналитической и токсикологической химии, д.фарм.н., профессор

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

Профессор кафедры фармацевтической химии с курсами аналитической и токсикологической химии, д.фарм.н., доцент

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

доцент кафедры фармакологии, к.фарм.н.

Светлана О. Шепилова, Bashkir State Medical University,3 Lenina St., Ufa 450008

аспирант кафедры фармацевтической химии с курсами аналитической и токсикологической химии

Ирина П. Байкова, Institute of Organic Chemistry, Ufa Scientific Center of the Russian Academy of Sciences, 71 Oktyabrya Ave., Ufa 450054

научный сотрудник лаборатории физико-химических методов анализа, к.х.н.

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Published

2020-10-14

Issue

Vol. 56 No. 9 (2020)

Section

Short Communications