Synthesis of Imidazole Spiro Compounds From 5-Alkoxycarbonyl-1H-Pyrrole-2,3-Diones and Phenylurea

5-Alkoxycarbonyl-substituted 1 H -pyrrole-2,3-diones react with phenylurea, forming alkyl 4-hydroxy-5-oxo-2-[(phenylcarbamoyl)amino]-2,5-dihydro-1 H -pyrrole-2-carboxylates, which cyclize in the presence of sodium methoxide, giving 8-hydroxy-3-phenyl-1,3,6-triazaspiro[4.4]-non-8-ene-2,4,7-triones. T...

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2016-07, Vol.52 (7), p.467-472
Main Authors: Dubovtsev, Aleksei Yu, Denislamova, Ekaterina S., Silaichev, Pavel S., Dmitriev, Maksim V., Maslivets, Andrey N.
Format: Article
Language:English
Subjects:
Alkyl groups
Carboxylates
Chemistry
Chemistry and Materials Science
Crystal structure
Diketones
Heterocyclic compounds
Imidazole
Organic Chemistry
Pharmacy
Spiro compounds
Thiophene
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Summary:5-Alkoxycarbonyl-substituted 1 H -pyrrole-2,3-diones react with phenylurea, forming alkyl 4-hydroxy-5-oxo-2-[(phenylcarbamoyl)amino]-2,5-dihydro-1 H -pyrrole-2-carboxylates, which cyclize in the presence of sodium methoxide, giving 8-hydroxy-3-phenyl-1,3,6-triazaspiro[4.4]-non-8-ene-2,4,7-triones. The crystal structures of 8-hydroxy-9-(4-methylbenzoyl)-3-phenyl-6-( p -tolyl)-1,3,6-triazaspiro[4.4]non-8-ene-2,4,7-trione and methyl 8-hydroxy-2,4,7-trioxo-3,6-diphenyl-1,3,6-triazaspiro[4.4]non-8-ene-9-carboxylate were studied.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-016-1913-8