Synthesis of Trifluoromethyl-Containing Imidazolidine-2-Thiones and Their Reactions with Urea, 2-Aminoethanol and 2-Aminophenol

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Abstract

The reaction of perfluorobiacetyl with thiourea, N-methyl- and N-phenylthiourea in acetonitrile afforded cis-, trans-isomers of 4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidine-2-thione and 1-methyl(phenyl)-4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidine-2-thiones in 92–95% yield. The interaction of 4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidine-2-thione with 2-aminoethanol (2-AE) affords thioxoimidazothiazolone, and the expected condensation product, thioimidazooxazine, is obtained as a minor product. An unusual reaction route of N-methylimidazolidine-2-thione with 2-AE was found, leading to thioxohydantoins: 5-[(2-hydroxyethyl)amino]-3-methyl-2-thioxo-5-(trifluoromethyl)imidazolidin-4-one and 5-hydroxy-3-methyl-2-thioxo-5-(trifluoromethyl)imidazolidin-4-one. The reaction of N-methylimidazolidine-2-thione with urea yields a condensation product of a different type, N-methylthioxoimidazooxolone, instead of the supposed thioglycoluril, as well as N-methyltrifluoromethylthioxohydantoin. Heating 1-phenyl-4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidine-2-thione with urea, 2-AE, and 2-aminophenol in dimethylacetamide yields an intramolecular rearrangement product, N-phenylbis(trifluoromethyl)thioxohydantoin.

About the authors

L. V Saloutina

Postovsky Institute of Organic Synthesis of Ural Branch of Russian Academy of Sciences; Ural Federal University named after the first President of Russia B.N. Yeltsin

Email: saloutinalv@yandex.ru
ORCID iD: 0000-0003-0468-1037
Ekaterinburg, Russia; Ekaterinburg, Russia

M. I Kodess

Postovsky Institute of Organic Synthesis of Ural Branch of Russian Academy of Sciences

ORCID iD: 0000-0003-4649-3659
Ekaterinburg, Russia

I. N Ganebnykh

Postovsky Institute of Organic Synthesis of Ural Branch of Russian Academy of Sciences

ORCID iD: 0000-0002-8487-8448
Ekaterinburg, Russia

V. I Saloutin

Postovsky Institute of Organic Synthesis of Ural Branch of Russian Academy of Sciences

Ekaterinburg, Russia

O. N Chupakhin

Ural Federal University named after the first President of Russia B.N. Yeltsin

ORCID iD: 0000-0002-1672-2476
Ekaterinburg, Russia

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