Synthesis of 3-trimethylsiloxy-1-(furan-3-yl)butadiene and its reactions with dienophiles

Synthesis of 3-trimethylsiloxy-1-(furan-3-yl)butadiene and its reactions with dienophiles Full article

Journal

Chemistry of Heterocyclic Compounds
ISSN: 0009-3122 , E-ISSN: 1573-8353

Output data

Year: 2016, Volume: 52, Number: 6, Pages: 364-373 Pages count : DOI: 10.1007/s10593-016-1897-4

Tags

dimethylbarbituric acid; furan-3-aldehyde; Meldrum's acid; siloxybutadienes; Diels-Alder reaction; X-ray structural analysis

Authors

Mironov Maxim E. ^1,2 , Bagryanskaya Irina Yu. ^1,2 , Shults Elvira E. ^1,2

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, 9 Akad Lavrentieva Ave, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk Natl Res State Univ, 2 Pirogova St, Novosibirsk 630090, Russia

3-Trimethylsilyloxy-1-(furan-3-yl)butadiene was synthesized and studied in reactions with 2,2-dimethyl-5-methylidene-1,3-dioxane-4,6-diones, 5-methylenepyrimidine-2,4,6-triones, as well as with imines. Reactions with dienophiles containing an exo-methylene double bond in the presence of L-proline occurred regio- and stereoselectively with the formation of 7-(furan-3-yl)spiro[5,5]undecane-1,5,9-triones or 7-(furan-3-yl)-2,4-diazaspiro[5.5]undecane-1,3,5,9-tetraones. The reaction of diene with methylene imine, obtained from L-phenylalanine methyl ester and formaldehyde, in the presence of Lewis acids led to the formation of 2-(furan-3-yl)piperidin-4-one or the product of ene reaction, methyl (2S)-2-{[(4E)-5-(furan-3-yl)-3-oxopent-4-en-1-yl]amino}-3-phenylpropanoate. The structures of three compounds were confirmed by X-ray structural analysis.

Mironov M.E. , Bagryanskaya I.Y. , Shults E.E.
Synthesis of 3-trimethylsiloxy-1-(furan-3-yl)butadiene and its reactions with dienophiles
Chemistry of Heterocyclic Compounds. 2016. V.52. N6. P.364-373. DOI: 10.1007/s10593-016-1897-4 WOS Scopus РИНЦ

Published print:	Jun 1, 2016
Published online:	Aug 9, 2016

Web of science	WOS:000382138200005
Scopus	2-s2.0-85028271715
Elibrary	41788374
OpenAlex	W2509202637