Cascade reactions of nitrogen-and phosphorus-containing ylides with methyl diazoacetate and in situ generated diazocyclopropane |
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Authors: | Yu V Tomilov D N Platonov D V Dorokhov I V Kostyuchenko |
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Institution: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation |
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Abstract: | Reactions of pyridinium or phosphorus ylides with diazo esters are multistep processes. The first step is covalent bonding
between the ylide C atom and the terminal N atom. This is followed by elimination of the ylide-forming molecule and successive
addition of one or two ylide fragments. Depending on the nature of the starting reagents, this type of transformations leads
to novel polyfunctional phosphorus ylides or, with pyridinium ylides, to polyalkyl 3,4(4,5)-diazaalkadienetri-or tetracarboxylates.
A reaction of the in situ generated diazocyclopropane with methyl triphenylphosphoranylideneacetate stops at the first step, giving a cyclopropylazo-containing
ylide. Reactions of the latter with acyl chlorides yield six-membered heterocyclic betaines with a triphenylphosphonium substituent.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 108–113, January, 2006. |
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Keywords: | diazo compounds pyridinium ylides phosphoranylidenes diazadienes azines heterocyclization |
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