An efficient, one-pot synthetic protocol toward spirooxindole derivatives containing 1,4-dihydropyridine-fused 1,3-diazaheterocycle fragments, a class of biologically active compounds starting from 1,1-bis(methylthio)-2-nitroethylene, 1,n-diamine, isatin, or its derivatives, and malononitrile is described. The reaction proceeds in ethanol in the presence of 10 mol% of piperidine as a basic catalyst under reflux conditions to produce the title compounds in 74-85% yields.
An efficient, one‐pot synthetic protocol for polyfunctionalized 1,4‐dihydropyridine‐fused‐1,3‐diazaheterocycles, a class of biologically active compounds, starting from 1,1‐bis(methylthio)‐2‐nitroethylene, 1,n‐diamine, arylaldehyde, and malononitrile is described. The reactions are completed within 12–15 h under refluxing conditions and in the presence of 10 mol % of piperidine as a basic catalyst to produce the title compounds in 60–75% yields.
An efficient, one-pot synthetic protocol toward a-alkylidene-g-butyrolacton-2-ones, a rather unexplored class of heterocyclic scaffolds starting from primary amines, methyl acetoacetate, and chloroacetyl chloride is described. The mixture of MeCNMeOH as a polar solvent triggers a new cycloaddition of the enaminone intermediate. The reaction is completed within 12 hours under reflux condition to produce the title compounds.
An efficient, facile, and simple route for the preparation of spirooxindole-containing fused 1,4-dihydropyridine derivatives through a one-pot, pseudo five-component condensation reaction of isatin or its derivatives, 1,1-bis(methylthio)-2-nitroethylene, 1,3-dicarbonyl compounds, and two equivalents of ammonia in water is reported. The merits of this method include the use of water as a green solvent, and inexpensive and easily available starting materials and catalyst, the high yield of products, and the straightforward work-up.
An efficient and simple route for the preparation of 2-oxopyridine-fused 1,3-diazaheterocyclic compounds via a three component reaction is described. It involves the reaction between alkylenediamines 1, 1,1-bis(methylsulfanyl)-2-nitroethene, and alkyl prop-2-ynoates 2 in refluxing THF (Table). The structures were corroborated by spectroscopic (IR, 1 H-and 13 C-NMR, and EI-MS) and elemental analyses. A plausible mechanism for this type of cyclization is proposed (Scheme).Introduction. -The development of new and simple methods for the efficient preparation of compounds containing 2-oxopyridine-fused 1,3-diazaheterocycle moieties is a beneficial and interesting challenge [1 -6]. As a part of our research program, which is aimed at developing libraries of bioactive compounds, and in continuation of our interest in one-pot and multicomponent reactions (MCRs), a three-component reaction toward fused heterocycles is described herein.
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