A "One Pot, " Environmentally Friendly, Multicomponent Synthesis of 2‐Amino‐5‐cyano‐4‐[(2‐aryl)‐1H‐indol‐3‐yl]‐6‐hydroxypyrimidines and Their Antimicrobial Activity. (25th March 2014)

• Record Type: Journal Article
• Authors: Gupta, Ragini; Jain, Anshu; Madan, Yogita; Menghani, Ekta
• Is Part Of: Journal of heterocyclic chemistry. Volume 51:Number 5(2014)
• Page Start: 1395
• Page End: 1403
• Publication Date: 2014-03-25
• Subjects: Heterocyclic compounds -- Periodicals; 547.59
• DOI: 10.1002/jhet.1796
• Languages: English
• ISSNs: 0022-152X

Abstract

<abstract abstract-type="main"> <title> <x xml:space="preserve">Abstract</x> </title> <p>A series of multifunctional 2‐amino‐5‐cyano‐4‐[(2‐aryl)‐1<italic>H</italic>‐indol‐3‐yl]‐6‐hydroxypyrimidines (<bold>4a</bold>, <bold>4b</bold>, <bold>4c</bold>, <bold>4d</bold>, <bold>4e</bold>, <bold>4f</bold>) was synthesized by <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">multicomponent reaction</named-content> of 3‐formylindole (<bold>1</bold>), cyanoethylacetate (<bold>2</bold>), and guanidine hydrochloride (<bold>3</bold>) with NaOH by using green chemical techniques, viz. <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">microwave irradiation</named-content> and grindstone technology. The same reactants when refluxed in ethanol also gave titled compounds (<bold>4a</bold>, <bold>4b</bold>, <bold>4c</bold>, <bold>4d</bold>, <bold>4e</bold>, <bold>4f</bold>). Compared with conventional procedure, the reaction can be carried out under milder conditions, requiring a shorter reaction time and giving higher yields following the <named-content content-type="chemicalTechnology" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">green chemistry</named-content> methodology. All the synthesized compounds have been characterized on the basis of elemental analyses and spectral data (IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR, and mass). All synthesized compounds were also evaluated for their <named-content content-type="chemicalTechnology" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">antimicrobial activity</named-content> against nine pathogenic bacteria, antifungal activity against <italic>Rhizopus stolonifer</italic>, <italic>Aspergillus flavus</italic>, and <italic>Fusarium oxysporum</italic> and <named-content content-type="chemicalTechnology" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">antibacterial activity</named-content> against <italic>Escherichia coli</italic> and <italic>Pseudomonas aeruginosa</italic> at different concentrations. Most of the compounds showed mild to moderate activity.</p> </abstract>