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 Full article
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Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393 |
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| Output data | Year: 2009, Volume: 45, Number: 1, Pages: 87-101 Pages count : 15 DOI: 10.1134/S1070428009010126 | ||||
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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 OpenAlex
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 OpenAlex
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 |