90361-81-2Relevant academic research and scientific papers
OXYGEN HETEROCYCLES BY SULPHUR YLIDE ANNULATION. IX. 3,4-DIHYDRO-2-HYDROXYMETHYL-2H,5H-PYRANOBENZOPYRAN-5-ONES FROM 3-(3-OXOALKYL)-4-HYDROXYCOUMARINS AND DIMETHYLSULPHOXONIUM METHYLIDE
Bravo, Pierfrancesco,Resnati, Giuseppe,Ticozzi, Calimero,Arnone, Alberto,Cavicchio, Giancarlo
, p. 501 - 510 (2007/10/02)
Several 3-(3-oxoalkyl)-4-hydroxycoumarins have been synthesized from the corresponding 4-hydroxycoumarins and they have been reacted with dimethylsulphoxonium methylide.Transfer of one methylene group to the carbonyl function takes place and the regio- and site-selective opening of the so formed epoxide by action of the oxygen in position 4 of the coumarin moiety gives 3,4-dihydro-2-hydroxymethyl-2H,5H-pyranobenzopyran-5-ones in medium to high yields.A full spectral characterization of twenty new products has been made, and a discussion on the different factors controlling the reaction mechanism is also reported.
REGIO- AND SITE-SELECTIVE HETEROANNULATION REACTION PROMOTED BY m-CHLOROPERBENZOIC ACID ON 3-(1,3-DISUBSTITUTED 3-BUTEN-1-YL)-4-HYDROXYCOUMARINS. SYNTHESIS OF 3,4-DIHYDRO-2-HYDROXYMETHYL-2H,5H-PYRANOBENZOPYRAN-5-ONES
Bravo, Pierfrancesco,Resnati, Giuseppe,Ticozzi, Calimero,Arnone, Alberto,Cavicchio, Giancarlo
, p. 491 - 500 (2007/10/02)
Epoxidation of 3-(1,3-disubstituted 3-buten-1-yl)-4-hydroxycoumarins, 1, bearing alkyl and aryl substituents with a slight molar excess of m-chloroperbenzoic acid gives 3,4-dihydro-2-hydroxymethyl-2H,5H-pyranobenzopyran-5-ones, 3, in medium to h
EPOXIDATION OF 3-(3'-BUTENYL)-4-HYDROXYCOUMARINS AND INTRAMOLECULAR 6-EXO CYCLIZATION TO 3,4-DIHYDRO-2-HYDROXYMETHYL-2H,5H-PYRANOBENZOPYRAN-5-ONES
Bravo, Pierfrancesco,Resnati, Giuseppe,Ticozzi, Calimero,Cavicchio, Giancarlo
, p. 1387 - 1390 (2007/10/02)
Several 3-(3'-butenyl)-4-hydroxycoumarins were synthetized and oxidized with m-chloroperbenzoic acid. 3,4-dihydro-2-hydroxymethyl-2H,5H-pyranobenzopyran-5-ones were obtained through an intramolecular 6-Exo cyclization of intermediate epoxide.
OXYGEN HETEROCYCLES BY SULPHUR YLIDE ANNULATION: SYNTHESIS OF 3,4-DIHYDRO-2H,5H-PYRANOBENZOPYRAN-5-ONES BY DIMETHYLSULPHONIUM METHYLIDE
Bravo, Pierfrancesco,Carrera, Paola,Resnati, Giuseppe,Ticozzi, Calimero,Cavicchio, Giancarlo
, p. 245 - 248 (2007/10/02)
3,4-Dihydro-2-hydroxymethyl-2H,5H-pyranobenzopyran-5-ones are the main products of the reaction of dimethylsulphoxonium methylide on Michael adducts of 4-hydroxycoumarins and α,β-unsaturated ketones.Minor quantities of 3,4-dihydro-2-hydroxymethyl-2H,5H-pyranobenzopyran-5-ones are also sometimes obtained.
