| Title: |
Reactions of Thiiranes with NH Heterocycles: II. C-Bromo/Nitro-1-(thietan-3-yl)pyrazoles as Convenient Synthons for Substituted 1-(Thietan-3-yl)pyrazoles. |
| Authors: |
Klen, E. E.1 (AUTHOR) klen_elena@yahoo.com, Makarova, N. N.1 (AUTHOR), Khaliullin, F. A.1 (AUTHOR), Shepilova, S. O.1 (AUTHOR), Ishkinina, A. R.1 (AUTHOR), Baikova, I. P.2 (AUTHOR) poljr@anrb.ru |
| Source: |
Russian Journal of Organic Chemistry. Sep2022, Vol. 58 Issue 9, p1192-1199. 8p. |
| Subject Terms: |
*PYRAZOLES, *HETEROCYCLIC compounds, *NUCLEOPHILES, *OXIDATION, *ALKYLATION, *NITROGEN compounds |
| Abstract: |
Reactions of 2-(chloromethyl)thiirane with symmetrically substituted C-bromo/nitropyrazoles in water in the presence of bases were accompanied by thiirane–thietane rearrangement to afford 4-bromo(nitro)- and 3,5-dibromo-4-bromo(nitro)-1-(thietan-3-yl)-1H-pyrazoles as convenient intermediate products for further transformations. Possible modifications of the title compounds via oxidation to 1-(1-oxo-λ4-thietan-3-yl)- and 1-(1,1-dioxo-λ6-thietan-3-yl)pyrazoles, reactions with oxygen and nitrogen nucleophiles with the formation of thietane-containing 5-methoxy- and 5-(morpholin-4-yl)-1H-pyrazoles, and reduction to 4-amino-3-bromo-5-(morpholin-4-yl)-1-(thietan-3-yl)-1H-pyrazole have been demonstrated. [ABSTRACT FROM AUTHOR] |
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