98934-52-2Relevant academic research and scientific papers
SYNTHESE D'HETEROCYCLES α-PHOSPHONIQUES. NOUVEAUX DEVELOPPEMENTS
Aboujaoude, Elie Elia,Collignon, Noel,Savignac, Philippe
, p. 231 - 244 (2007/10/02)
Synthesis of α-phosphonic heterocycles is described by condensation of 1,2- 1,3- or 1,4-bisnucleophiles with β-phosphonic enamines 2 bearing a functional group.From guanidine and analogs 4-diethoxyphosphinyl pyrimidines 5 and 8 are obtained with yields up to 50percent .Substituted hydrazines give 4-diethoxyphosphinyl pyrazoles 11 with very good yields.With hydroxylamine a spontaneous dehydration gives the enolic form 18 of a β-ketophosphonate α-nitrile.Orthophenylene diamine is a special example in fact the departure β-ketophosphonate is recovered with benzimidazole elimination.
DIALKYL FORMYL-1 METHYLPHOSPHONATES α-FONCTIONNELS-II. PREPARATION PAR VOIE THERMIQUE ET TRANSFORMATION EN HETEROCYCLES α-PHOSPHONIQUES
Aboujaoude, Elie Elia,Collignon, Noel,Savignac, Philippe
, p. 427 - 434 (2007/10/02)
The thermal condensation of functional phosphonates bearing strongly withdrawing groups (RO)2P(O)CH2Z 1 with dimethylformamide dimethyl acetal gives corresponding β-functional, β-phosphonic enamines (RO)2P(O)C(Z)=CHNMe2 2.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.
