Synthesis of 3a,4,6a-triphenylimidazothiazoledione and 2-thioxo-3a,6,6a-triphenylimidazooxazolone in the reaction of 5-hydroxy-1,4,5-triphenyl-1H-imidazol-2(5H)-one with KSCN and AcOH

The study of the reaction of 5-hydroxy-1,4,5-triphenyl-1 H -imidazol-2(5 H )-one with KSCN and AcOH showed that it leads to the formation of 3a,4,6a-triphenyltetrahydro-2 H -imidazo[4,5- d ]thiazole-2,5(3 H )-dione ( 1a ) and 2-thioxo-3a,6,6a-triphenyltetrahydro-2 H -imidazo[4,5- d ]oxazol-5(3 H )-o...

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Bibliographic Details
Published in:Russian chemical bulletin 2024-09, Vol.73 (9), p.2772-2777
Main Authors: Baranov, V. V., Antonova, M. M., Aksenova, S. A., Kravchenko, A. N.
Format: Article
Language:English
Subjects:
Brief Communications
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Crystallization
Inorganic Chemistry
Organic Chemistry
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Summary:The study of the reaction of 5-hydroxy-1,4,5-triphenyl-1 H -imidazol-2(5 H )-one with KSCN and AcOH showed that it leads to the formation of 3a,4,6a-triphenyltetrahydro-2 H -imidazo[4,5- d ]thiazole-2,5(3 H )-dione ( 1a ) and 2-thioxo-3a,6,6a-triphenyltetrahydro-2 H -imidazo[4,5- d ]oxazol-5(3 H )-one ( 2b ) with the predominant formation of the former one. The structures of compounds 1a and 2b were confirmed by X-ray diffraction analysis on the examples of solvate 1a • AcOH and monohydrate 2b • H 2 O obtained by crystallization from AcOH and a mixture of EtOH—H 2 O (1: 10), respectively.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-024-4391-7