Tandem synthesis of functionalized hexaalkyl benzoisoquinolinopyrrolonaphthyridine-hexacarboxylate, via isoquinoline based multi-component reaction

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 Synthesis of Regioselective Polysubstituted Indolizines via Three‐Component Reactions of Dialkyl Acetylendicarboxylates, Dialkylchloro Malonates, and Pyridines

“…Presumably, the zwitterionic intermediate 5a formed from pyridine 1a and dimethylacetylene dicarboxylate 2a is protonated by 3a to furnish intermediate 6a , which is attacked by carbanion 7a , to produce 8a . The subsequent cyclization of intermediate 8a followed by the elimination of the HCl leads to produced intermediate 9a . The intermediate 9a is finally converted to 4a by elimination of HCO 2 Et.…”

An efficient synthesis of novel benzo[b]pyrido[3′,2′:4,5]thieno[2,3-e][1,6]naphthy-ridine-8-ones

“…They are associated with a wide spectrum of biological effects such as anticancer [3], anti-HIV-1 [4], antimicrobial [5] and cytotoxic activities [6]. Therefore, the synthesis of 1,6-naphthyridine derivatives has aroused great interest in organic and medicinal chemistry communities [7][8][9][10][11].…”