A catalyst-free multicomponent domino sequence for the diastereoselective synthesis of (E)-3-[2-arylcarbonyl-3-(arylamino)allyl]chromen-4-ones
نویسندگان
چکیده
The three-component domino reactions of (E)-3-(dimethylamino)-1-arylprop-2-en-1-ones, 3-formylchromone and anilines under catalyst-free conditions afforded a library of novel (E)-3-(2-arylcarbonyl-3-(arylamino)allyl)-4H-chromen-4-ones in good to excellent yields and in a diastereoselective transformation. This transformation generates one C-C and one C-N bond and presumably proceeds via a reaction sequence comprising a Michael-type addition-elimination reaction, a nucleophilic attack of an enamine to a carbonyl reminiscent of one of the steps of the Bayllis-Hilman condensation, and a final deoxygenation. The deoxygenation is assumed to be induced by carbon monoxide resulting from the thermal decomposition of the dimethylformamide solvent.
منابع مشابه
Chemodivergent, One-Pot, Multi-Component Synthesis of Pyrroles and Tetrahydropyridines under Solvent- and Catalyst-Free Conditions Using the Grinding Method.
A highly efficient, chemoselective synthesis of a library of polysubstituted pyrroles and tetrahydropyridines has been achieved through the one-pot, multicomponent reactions of ethyl (E)-3-(aryl/alkyl amino) acrylates, 2,2-dihydroxy-1-arylethan-1-ones, and malononitrile under solvent- and catalyst-free grinding conditions. The selective formation of pyrrole or tetrahydropyridines relied on subs...
متن کاملFacile one-pot multicomponent synthesis of 2-amino-6-(2-oxo-2H-chromen- 3-yl)-4-arylpyridine-3-carbonitriles using Brønsted acidic ionic liquid as catalyst under solvent-free conditions
A series of 2-amino pyridine-3-carbinitrile derivatives incorporated coumarin moiety has developed via multicomponent condensation of 3-acetyl-2H-chromen-2-one, arylaldehydes, malononitrile and ammonium acetate utilizing Brønsted acidic ionic liquid, (4-sulfobutyl)tris(4-sulfophenyl)phosphonium hydrogen sulfate as catalyst under solvent-free conditions. Good yields, short reaction times, straig...
متن کاملFacile one-pot multicomponent synthesis of 2-amino-6-(2-oxo-2H-chromen- 3-yl)-4-arylpyridine-3-carbonitriles using Brønsted acidic ionic liquid as catalyst under solvent-free conditions
A series of 2-amino pyridine-3-carbinitrile derivatives incorporated coumarin moiety has developed via multicomponent condensation of 3-acetyl-2H-chromen-2-one, arylaldehydes, malononitrile and ammonium acetate utilizing Brønsted acidic ionic liquid, (4-sulfobutyl)tris(4-sulfophenyl)phosphonium hydrogen sulfate as catalyst under solvent-free conditions. Good yields, short reaction times, straig...
متن کاملD-tartaric acid: a novel catalyst for green and efficient synthesis of 3,4-dihydropyrimidin-2(1H)-ones by Biginelli reaction under solvent-free conditions
D-tartaric acid is successfully used as a green and efficient catalyst for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones under solvent-free conditions. The developed method has many advantages, including devoid of harmful catalyst and solvents, high yield and easily work-up.
متن کاملHighly efficient multicomponent Biginelli’s synthesis of 3,4-dihydropyrimidin-2(1H)-ones catalyzed by Al-MCM-41 under solvent-free conditions
In this study, an efficient and green process for the synthesis of dihydropyrimidin-2(1H)-ones from aromatic benzaldehydes, ethyl acetoacetate and urea using Al-MCM-41 as heterogeneous catalyst and microreactor under solvent-free conditions has been developed. The advantages of this method are easy work-up procedure, regeneration of the catalyst, clean and neutral reaction conditions.
متن کامل