Dialkyl formyl-1 methylphosphonates α-fonctionnels—II : Preparation par voie thermique et transformation en heterocycles α-phosphoniques |
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| Authors: | Elie Elia Aboujaoude Noël Collignon Philippe Savignac |
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| Institution: | Laboratoire des Composés Organophosphorés-I.N.S.C.I.R., BP 08, F 76130 Mont-Saint-AignanFrance;Equipe CNRS-SNPE, 2-8 rue Henry Dunant, BP 28, F 94320 ThiaisFrance |
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| Abstract: | The thermal condensation of functional phosphonates bearing strongly withdrawing groups (RO)2P(O)CH2Z1 with dimethylformamide dimethyl acetal gives corresponding β-functional, β-phosphonic enamines (RO)2P(O)C(Z)=CHNMe22. Acid or basic hydrolysis of the enamines frequently gives the free aldehyde (RO)2P(O)CH(Z)—CHO 3. We show that the enamines can be used with success for the synthesis of heterocycles like, pyrazoles 4, pyrimidines 5, benzodiazepine 6 or indole 7, all of them substituted with a phosphonate group. |
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