Flavonoids, 40.+ Synthesis of 3-alkyl- and -arylthioflavanones and their transformations into sulfur-containing flavonoids

doi:10.1016/S0040-4020(01)81494-0

Tetrahedron

Volume 43, Issue 8, 1987, Pages 1827-1834

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Abstract

trans-3-Mesyloxyflavanones 1 were converted into cis- and trans-3-(alkylthio)- and -(phenylthio) flavanones 2-4 by nucleophilic substitution reaction with thiols or thiolates. Flavanones 2-4 were useful intermediates in the synthesis of various sulfur-containing derivatives; flavanones, flavones and dihydrochalcones possessing alkyl- or arylthio, -sulfinyl and -sulfonyl group. Oxidation of cis- and trans- isomers of 4 led to completely different products.

Reference (19)

PatonayT. et al.
Tetrahedron
(1984)
PatonayT. et al.
Liebigs Ann. Chem.
(1979)
PatonayT. et al.
Acta Chim. Acad. Sci. Hung.
(1981)
LisselM.
J. Chem. Res. (S)
(1982)
LisselM.
J. Chem. Res. (M)
(1982)
SimonsS.S. et al.
J. Org. Chem.
(1980)
Fujita
Tetrahedron Lett.
(1978)
MatsuuraS. et al.
Chem. Pharm. Bull.
(1978)
UminoN. et al.
Chem. Abs.
(1975)
UminoN. et al.
Chem. Abs.
(1976)

There are more references available in the full text version of this article.

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¹: Part 39. see ref. 1.

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Flavonoids, 40.+ Synthesis of 3-alkyl- and -arylthioflavanones and their transformations into sulfur-containing flavonoids1

Abstract

Tetrahedron

Liebigs Ann. Chem.

Acta Chim. Acad. Sci. Hung.

J. Chem. Res. (S)

J. Chem. Res. (M)

J. Org. Chem.

Tetrahedron Lett.

Chem. Pharm. Bull.

Chem. Abs.

Chem. Abs.

Flavonoids, 40.⁺ Synthesis of 3-alkyl- and -arylthioflavanones and their transformations into sulfur-containing flavonoids¹