130184-70-2Relevant academic research and scientific papers
DABCO-mediated [4+2] annulation of but-3-yn-2-one and activated ketones: Facile preparation of 2,3-dihydropyran-4-one
Lian, Zhong,Zhao, Qian-Yi,Wei, Yin,Shi, Min
supporting information; experimental part, p. 3338 - 3341 (2012/07/01)
We found that nitrogen-containing Lewis base mediated [4+2] annulation of but-3-yn-2-one with activated ketones could proceed efficiently to give the corresponding 2,3-dihydropyran-4-ones in moderate to good yields under mild conditions. The substrate scope has been carefully examined. Moreover, a plausible reaction mechanism for the [4+2] annulation of but-3-yn-2-one with activated ketones mediated by DABCO has been proposed on the basis of previous literature and our own investigations. Copyright
CYCLOADDITION OF 1-METHOXY-3-TRIMETHYLSILYLOXYBUTADIENE WITH HALOGENATED CARBONYL COMPOUNDS
Sera, Akira,Iwasaki, Yasuji,Umeda, Michio,Itoh, Kuniaki
, p. 273 - 278 (2007/10/02)
Cycloadditions of 1-methoxy-3-trimethylsilyloxy-1,3-butadiene (1) with halogenated carbonyl compounds (2) yielded corresponding substituted tetrahydro- and/or dihydropyran-4-ones (3 and/or 4).Lewis acids were found to be effective as catalysts.Reactions with less reactive carbonyl compounds (2c,d) afforded p-hydroxyacetophenone (5) produced by cyclodimerization of 1.Stereochemistry of the adducts was deduced by 1H nmr spectroscopy.
Stabilisation of the Thromboxane Ring System by Electron-withdrawing Substituents: Synthesis and Attempted Cyclisation of Substituted Tetrahydropyran-2,4-diols
Kirby, Anthony J.,Ryder, Hamish,Matassa, Victor
, p. 617 - 626 (2007/10/02)
The hetero Diels-Alder reaction of trifluoromethyl ketones and 1-benzyloxy-3-trimethylsilyloxybutadiene is developed as a route to 4-hydroxytetrahydropyranyl acetal derivatives.Several 6,6-disubstituted tetrahydropyran-2,4-diols have been prepared, and th
