2008
DOI: 10.1016/j.tetlet.2008.01.054
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Facile and efficient synthesis of a new class of bis(3′-indolyl)pyridine derivatives via one-pot multicomponent reactions

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Cited by 101 publications
(34 citation statements)
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“…[13] Recently, we reported a metal-free Michael addition initiated three-component substrate directed route to polysubstituted pyridines 4 from 1,3-dicarbonyls 1 that could solve part of the selectivity substitution problem (Scheme 1). [14] This simple and totally regioselective multicomponent reaction (MCR) combines molecular complexity and diversity [15] with economic [16] and environmental aspects. [17] However, this methodology was limited to the use of b-unsubstituted aldehydes and ketones 2 (R 3 , R 4 = H, alkyl), probably because of the reversibility of the Michael addition with hindered substrates; this prevents any access to 4-substituted pyridines and limits the functional diversity at the strategic 2-position.…”
mentioning
confidence: 99%
“…[13] Recently, we reported a metal-free Michael addition initiated three-component substrate directed route to polysubstituted pyridines 4 from 1,3-dicarbonyls 1 that could solve part of the selectivity substitution problem (Scheme 1). [14] This simple and totally regioselective multicomponent reaction (MCR) combines molecular complexity and diversity [15] with economic [16] and environmental aspects. [17] However, this methodology was limited to the use of b-unsubstituted aldehydes and ketones 2 (R 3 , R 4 = H, alkyl), probably because of the reversibility of the Michael addition with hindered substrates; this prevents any access to 4-substituted pyridines and limits the functional diversity at the strategic 2-position.…”
mentioning
confidence: 99%
“…The spirooxindole framework [2], represents an important structural organization present in a number of bioactive natural products, such as coerulescine, horstiline, welwitindolinone A, Spirotryprostatin A, [3] a natural alkaloid isolated from the fermentation broth of Aspergillus fumigates, has been identified as a novel inhibitor of microtubule assembly and the function of muscarinic serotonin receptors [4].The 3-substituted indole nucleus substructure is one of the important heterocycles found in natural products, pharmaceuticals and is important in medicinal chemistry [5]. Its scaffolds are found in a number of biologically active compounds with anticancer,anti-tumour [6], antiinflammatory, hypoglycemic, analgesic and anti-pyretic activities. Many indole alkaloids are recognized as marine invertebrate metabolites for their broad spectrum of biological properties [7].…”
Section: Introductionmentioning
confidence: 99%
“…16,17 Through appropriate functional group modifications, these scaffolds are capable of providing ligands for a number of functionally and structurally discrete biological receptors. 3-Substitued indole scaffolds are found in a number of biologically active compounds especially with anticancer, anti-tumour, 18 hypoglycemic, anti-inflammatory, analgesic and anti-pyretic activities (figure 1). [19][20] The wide-ranging biological activity associated with many pyridine and 3-substituted indole derivatives, both naturally occurring and synthetic, ensures that the synthesis of this important ring system remains a topic of current interest.…”
Section: Introductionmentioning
confidence: 99%
“…[21][22][23][24][25] There have been very few reports about the synthesis of indol-3-yl derivatives including pyridine moieties. 9,18,[22][23]26 As part of our ongoing research on the development of novel synthetic routes for the synthesis of biologically active hetero- cyclic compounds and use of green chemical techniques in organic synthesis, 27,28 we report here a simple and facile one pot procedure for the synthesis of indol-3-yl pyridine derivatives in aqueous media under reflux condition.…”
Section: Introductionmentioning
confidence: 99%