Abstract: 5-Isopropenyl-2,3-dihydrothiophene 1,1-dioxide reacted with 5-methylidenepyrimidine-2,4,6-triones and 5-methylidene-2-thioxopyrimidine-4,6-diones in the presence of chiral amines or amino acids with high regio- and stereoselectivity to give optically active derivatives of barbituric and thiobarbituric acids spirofused at the 5-position to 1-benzothiophene 1,1-dioxide fragment. The reaction of 5-isopropenyl-2,3-dihydrothiophene 1,1-dioxide with 5-(2-methoxybenzylidene)-2-thioxopyrimidine-4,6-dione (generated in situ from 2-methoxybenzaldehyde and thiobarbituric acid) in the presence of (-)-ephedrine or L-4-(tert-butyldimethylsiloxy) proline gave the corresponding 2-thioxospiro[1-benzothiophene-4,5'-pyrimidine]-4',6'-dione 1,1-dioxide with an enantiomeric excess of 80%.

Cite: Shul'ts E.E. , Andreev G.N. , Shakirov M.M. , Komarova N.I. , Bagryanskaya I.Y. , Gatilov Y.V. , Tolstikov G.A.
Diels-alder reactions with cyclic sulfones: VIII. Organic catalysis in the synthesis of spiro[1-benzothiophene-4,5 '-pyrimidine]-2 ',4 ',6 '-trione 1,1-dioxides and 2 '-thioxospiro[1-benzothiophene-4,5 '-pyrimidine]-4 ',6 '-dione 1,1-dioxides
Russian Journal of Organic Chemistry. 2009. V.45. N1. P.87-101. DOI: 10.1134/S1070428009010126 WOS Scopus РИНЦ

Dates:

Published print:	Jan 1, 2009
Published online:	Feb 17, 2009

Identifiers:

Web of science	WOS:000263507800012
Scopus	2-s2.0-60849100508
Elibrary	13609454
OpenAlex	W2089854153

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