Cascade reactions of diazocarbonyl compounds with pyridinium aroylmethylides accompanied by water or benzoic acid elimination in the cyclocondensation step |
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Authors: | Dorokhov D V Platonov D N Suponitsky K Yu Tomilov Yu V |
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Institution: | 1.N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation ;2.A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation ; |
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Abstract: | The reaction of pyridinium aroylmethylides with diazocarbonyl compounds proceeds as a multistep process involving three ylide
molecules and one diazo compound molecule. As a result, intermediate functionally substituted azines, if they contain carbonyl
groups and reactive methylene fragment, undergo intramolecular cyclocondensation to form tri- and tetrasubstituted pyridazines.
Depending on stereochemistry of cyclic ketols formed, water or benzoic acid is eliminated to form tetra- or trisubstituted
pyridazines, respectively. The regularities of reactions of pyridinium ylides with diazo compounds are discussed depending
on the nature of substituents in the both substrates and reaction conditions. |
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