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dc.contributor.authorYugandar, S.
dc.contributor.authorKonda, S.
dc.contributor.authorParameshwarappa, G.
dc.contributor.authorIla, H.
dc.identifier.citationYugandar, S.; Konda, S.; Parameshwarappa, G.; Ila, H., One-Pot Synthesis of 2,4,5-Trisubstituted Imidazoles via 2+2+1 Cycloannulation of 1,3-Bishet(aryl)-monothio-1,3-diketones, alpha-Substituted Methylamines and Sodium Nitrite through alpha-Nitrosation of Enaminones. Journal of Organic Chemistry 2016, 81 (13), 5606-5622
dc.identifier.citationJournal of Organic Chemistryen_US
dc.descriptionRestricted Accessen_US
dc.description.abstractAn efficient one-pot synthesis of a series of diversely functionalized trisubstituted 4(5)het(aroyl)-2,5(4)-het(aryl)/alkylimidazoles from readily available 1,3-bishet(aryl)monothio-1,3-diketones has been reported. This novel sequential one-pot, three step protocol, wherein three new carbon nitrogen bonds are formed in contiguous fashion, involves in situ generation of enaminones by reaction of monothio-1,3-diketones with alpha-substituted methylamines, followed by their alpha-nitrosation with sodium nitrite and subsequent base mediated intramolecular heterocyclization of the resulting alpha-hydroxyiminoimines to trisubstituted imidazoles in high yields under mild conditions. These newly prepared 4(5)-het(aroyl)-5(4)-het(aryl)/alkylimidazoles are shown to exist as tautomeric mixture, however, their subsequent alkylation with methyl iodide in the presence of potassium carbonate affords 1-N-methy-2,5-bishet(aryl)-4-het(aroyl)imidazoles in highly regioselective fashion in most of the cases. Synthesis of few 4(5)-(2-hydroxyphenyl)-2,5(4)-substituted imidazoles, which are known to be good coordinating ligands, has also been reported. A probable mechanism for the formation of these imidazoles from hydroxyiminoimine intermediates has also been suggested.en_US
dc.publisherAmerican Chemical Societyen_US
dc.rights@American Chemical Society, 2016en_US
dc.subjectDiversity-Oriented Synthesisen_US
dc.subjectOxidative Coupling Reactionen_US
dc.subjectBond-Forming Reactionsen_US
dc.subjectHetero-Fused Analogsen_US
dc.subjectTetrasubstituted Imidazolesen_US
dc.subjectMulticomponent Synthesisen_US
dc.subject1,2,4,5-Tetrasubstituted Imidazolesen_US
dc.subjectComplementary Regioselectivityen_US
dc.subjectTrisubstituted Imidazolesen_US
dc.subjectMultisubstituted Indolesen_US
dc.titleOne-Pot Synthesis of 2,4,5-Trisubstituted Imidazoles via [2+2+1] Cycloannulation of 1,3-Bishet(aryl)-monothio-1,3-diketones, alpha-Substituted Methylamines and Sodium Nitrite through alpha-Nitrosation of Enaminonesen_US
Appears in Collections:Research Papers (H. Ila)

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