Synthesis of 3,4-Dihydropyridin-2(1H)-ones and 3,4-Dihydro-2H-pyrans via Four-Component Reactions of Aromatic Aldehydes, Cyclic 1,3-Carbonyls, Arylamines, and Dimethyl Acetylenedicarboxylate

Abstract

A protocol has been developed for the efficient synthesis of structurally diverse 3,4-dihydropyridin-2(1H)-ones and 3,4-dihydro-2H-pyrans via four-component reactions of arylamines, acetylenedicarboxylate, aromatic aldehydes and cyclic 1,3-diketones. The selective formation of the very different pyridinone or pyran derivatives depends on the structure of cyclic 1,3-diketone. The key steps are proposed to involve Michael addition of the enamino ester formed in situ from the reaction of arylamine with dimethyl acetylenedicarboxylate to arylidine cyclic 1,3-diketones.

Convenient Construction of Indanedione‐Fused 2,5‐Dihydropyridines, 4,5‐Dihydropyridines, and Spirooxindolines

“…The outcome of this reaction is very similar to our previously reported four‐component reaction of arylamines, acetylenedicarboxylate, isatins, and dimedone for the preparation of spiro[indoline‐3,2′‐quinolines]. [16c] Thus, a new reaction mechanism for the formation of compounds 3a – 3i is proposed in Scheme , based on previously reported reactions. In acetic acid as solvent, the reaction of 1,3‐indanedione with dimethyl acetylenedicarboxylate first gave an adduct D .…”

“…Recently, we reported the four‐component reaction of an arylamine, dimethyl acetylenedicarboxylate, an aromatic aldehyde, and dimedone in ethanol with triethylamine as a basic catalyst, which leads to the formation of 3,4‐dihydro‐2 H ‐pyran derivatives . In view of the fact that 1,3‐indanedione is also a reactive cyclic 1,3‐diketone, we carried out the above four‐component reaction using 1,3‐indanedione to replace the dimedone.…”

Efficient Synthesis of the Functionalized Spiro[indoline‐3,4′‐pyridine] via Four‐component Reaction

“…[10][11][12][13][14][15][16][17][18][19][20][21] Recently multicomponent reactions based on the sequential reactions of isatins [22,23] or benzofuran-2,3-diones [24,25] with Huisgen's 1,4-dipoles, which were formed in situ from the addition of azaarenes with electron-deficient alkynes have been successfully used to construct versatile spirooxindole systems. [27] As a part of our program on the study of the reactivity of active β-enamino esters derived from the reaction of electrondeficient alkynes with primary arylamines, [28][29][30] herein we wish to report the efficient synthesis of the novel spiro[indoline-3,4'-pyridine] derivatives via four-component reaction of arylamine, acetylenedicarboxylate, isatins and malononitrile. [26] Recently Balalaie and coworkers also reported this four-compoenent reaction for the synthesis of 1,4-dihydropyridines by using (NH 4 ) 2 HPO 4 as a base in aqueous media.…”

Diastereoselective Synthesis of Functionalized Tetrahydropyrimidin‐2‐thiones via ZnCl2 Promoted One‐pot Reactions

“…[3][4][5] A number of domino and multicomponent reactions have been developed by using β-enaminones and β-enamino esters to react further with sequential adding nucleophilic or electrophilic reagents to give versatile heterocyclic systems. [11][12][13][14][15][16][17][18][19][20] Against this background and also in the context of our investigations to develop new domino reactions, herein we report the diastereoselective synthesis of functionalized tetrahydropyrimidin-2-thiones via ZnCl 2 promoted one-pot reactions of cyclic amine, methyl propiolate, aromatic aldehydes and thiourea. [11][12][13][14][15][16][17][18][19][20] Against this background and also in the context of our investigations to develop new domino reactions, herein we report the diastereoselective synthesis of functionalized tetrahydropyrimidin-2-thiones via ZnCl 2 promoted one-pot reactions of cyclic amine, methyl propiolate, aromatic aldehydes and thiourea.…”