Three-component one-pot synthesis of quinoline–furan conjugates from acetylenedicarboxylate, isocyanide, and 2-chloroquinoline-3-carbaldehyde

Isocyanide-based multicomponent reactions in the synthesis of heterocycles

“…The organic segment is connected to the isocyanide group via the nitrogen atom, not via the carbon. They are used as privileged synthons for the synthesis of other organic compounds in particular various heterocycles [23][24][25][26][27][28][29][30][31][32][33][34][35][36][37] , frequently via multicomponent reactions (MCRs) namely isocyanide multicomponent reactions (IMCRs) 25,[38][39][40][41][42][43][44][45][46][47][48][49] . Noticeably isocyanides are susceptible to polymerization 50 .…”

Synthesis and solid-state supramolecular chemistry of a series of pyridinium-derived zwitterions

“…In particular, there has been a large amount of work focussed on the reaction between dimethyl acetylenedicarboxylate (DMAD) and related esters with pyridines and other N-containing heterocycles. 1,2,[7][8][9][10] The zwitterionic intermediates in these reactions are seldom isolated, as they undergo rapid reaction and/or isomerisation to yield the final target product. 1,2,6 For a more detailed account of these reactions, the in-depth review 3 by Nair and colleagues should be consulted.…”

“…1,2 These reactions proceed via addition of the N-heterocycle to DMAD to form a dipolar intermediate, followed by subsequent reaction with a second equivalent of DMAD to produce a variety of heterocyclic compounds such as substituted quinolizones. Reactions including Huisgen cycloadditions, 6,[11][12][13][14] Morita-Baylis-Hillman type reactions (MBH), 15, 16 Diels-Alder reactions 3,17 and multi-component reactions [7][8][9][10] have all been known to employ these acetylene-derived zwitterions. In more recent research, the zwitterionic intermediate is most often produced en route to more complex heterocyclic compounds in multi-component reactions (MCR).…”

One‐Pot Construction of Bis‐Heterocycles through Isocyanide Based Multicomponent Reactions

“…In 2013, M. Ghandi and N. Zarezadeh described the synthesis of bound type functionalized furyl-quinoline BHCs 52 via a cascade condensation/Michael addition/intramolecular cyclization and [1,5] H shift rearrangement. [67] The reaction of 2chloro-3-formylquinolines with acetylene-dicarboxylates and isocyanides in acetonitrile solvent afforded the final products in 75-96 % yield (Scheme 29). The proposed reaction mechanism involves an initial generation of Huisgen's zwitterion 50 a, via 1 : 1 interaction between acetylene-dicarboxylates and isocyanides, which then attacks preferentially from its C-4 position on 2-chloroquinoline-3-carboxaldehyde to give an intermediate 51.…”