An Efficient Multicomponent Reaction Involving the Interception of the Zwitterionic Intermediate between DMAD and Isocyanides with Some Active Methylene Compounds

Ionic Liquid Promoted Efficient and Rapid One-pot Synthesis of Pyran Annulated Heterocyclic Systems

“…Recently, the one-pot synthesis of pyran annulated heterocyclic systems from condensation of 4-hydroxycoumarin [14] or 4-hydroxy-6-methylpyrone [14] or 1,3-dimethylbarbituric acid [15] with relatively expensive reagent such as dimethyl acetylenedicarboxylate and isocyanide has been reported in toxic benzene under reflux conditions. In addition, a new method based on multi-component reaction strategy using microwave heating in the solid state has been presented [16], but requires special instrument.…”

Current Developments in Michael Addition‐Based Multicomponent Domino Reactions Involving 1,3‐Dicarbonyls and Derivatives

“…1,3-Dicarbonyls can also be used in combination with isocyanide derivatives in Michael addition-initiated MCR sequences. As an illustration, in 2002, Nair et al reported on a novel approach to pyran annulated heterocyclic systems, through an efficient MCR involving the interception by some active methylene compounds of the zwitterionic intermediate arising from the conjugate addition of isocyanides to dimethyl acetylenedicarboxylate [38]. For example, treatment of 4-hydroxycoumarin with dimethyl acetylenedicarboxylate and stoichiometric amount of cyclohexyl cyanide in refluxing benzene afforded the corresponding product in 68% yield (Scheme 11).…”

Diels‐alder reaction of 1‐methyl‐3,6,8‐trinitro‐2‐quinolone

“…From the viewpoint of biological and pharmacological interests, syntheses of unnatural compounds possessing the MeQone skeleton are also important projects [6][7][8][9][10], however, direct functionalization of MeQone is not always easy because of its low reactivity. Recently, Fujita and coworkers reported the Diels-Alder reactions of quinolone derivatives having an electron-withdrawing group at the 3-or 4-positions [11][12][13].…”