Secondary amine-initiated three-component synthesis of 3,4-dihydropyrimidinones and thiones involving alkynes, aldehydes and thiourea/urea
نویسندگان
چکیده
The three-component reactions of aldehydes, electron deficient alkynes and ureas/thioureas have been smoothly performed to yield a class of unprecedented 3,4-dihydropyrimidinones and thiones (DHPMs). The reactions are initiated by the key transformation of an enamine-type activation involving the addition of a secondary amine to an alkyne, which enables the subsequent incorporation of aldehydes and ureas/thioureas. This protocol tolerates a broad range of aryl- or alkylaldehydes, N-substituted and unsubstituted ureas/thioureas and alkynes to yield the corresponding DHPMs with specific regioselectivity.
منابع مشابه
Brønsted Acidic Ionic Liquid: An Efficient and Reusable Catalyst for the Multi-Component Synthesis of Dihydropyrimidinones under Solvent-Free Conditions
An efficient and convenient procedure for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones and thiones by condensation of 1,3-dicarbonyl compounds, Aromatic and aliphatic aldehydes, and urea or thiourea in the presence of catalytic amount of Brønsted acidic ionic liquid 3-methyl-1-sulfonic acid imidazolium chloride {[Msim]Cl} under thermal solvent-free conditions reacted easily to afford the co...
متن کاملBronsted Acidic Ionic Liquid: An Efficient and Reusable Catalyst for the Multi-Component Solvent-Free Synthesis of Dihydropyrimidinones
An efficient and convenient procedure for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones and thiones by condensation of 1,3-dicarbonyl compounds, Aromatic and aliphatic aldehydes, and urea or thiourea in the presence of catalytic amount of Brønsted acidic ionic liquid 3-methyl-1-sulfonic acid imidazolium chloride {[Msim]Cl} under thermal solvent-free conditions reacted easily to afford the co...
متن کاملBrønsted Acidic Ionic Liquid: An Efficient and Reusable Catalyst for the Multi-Component Synthesis of Dihydropyrimidinones under Solvent-Free Conditions
An efficient and convenient procedure for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones and thiones by condensation of 1,3-dicarbonyl compounds, Aromatic and aliphatic aldehydes, and urea or thiourea in the presence of catalytic amount of Brønsted acidic ionic liquid 3-methyl-1-sulfonic acid imidazolium chloride {[Msim]Cl} under thermal solvent-free conditions reacted easily to afford the co...
متن کاملSynthesis of 3,4-Dihydropyrimidin-2(1H)-Ones and Their Corresponding 2(1H)Thiones Using Trichloroacetic Acid as a Catalyst under Solvent-Free Conditions
Trichloroacetic acid was found to be a convenient catalyst for the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones and their corresponding 2(1H)-thiones through a one-pot three-component reaction of aldehydes, alkyl acetoacetate, and urea or thiourea at 70°C under solvent-free conditions.
متن کاملThree Component Reaction: An Efficient Synthesis and Reactions of 3,4-Dihydropyrimidin-2(1H)-Ones and Thiones Using New Natural Catalyst
Synthesis of 3,4-dihydropyrimidin-2(1H)-one and 3,4-dihydropyrimidin-2(1H)-thione derivatives from aldehydes, 1,3-dicarbonyl derivatives and urea or thiourea using granite and quartz as new, natural and reusable catalysts. Some of the 3,4-dihydropyrimidin-2(1H)-thione derivatives were used to prepare new heterocyclic compounds. The antimicrobial activity of selected examples of the synthesized ...
متن کامل