1069073-94-4Relevant articles and documents
Synthesis of new (3-aminopyrrolidin-3-yl)phosphonic acid - A cucurbitine analogue - and (3-aminotetrahydrothiophen-3-yl)phosphonic acid via phosphite addition to heterocyclic hydrazones
Rabasso, Nicolas,Fadel, Antoine
experimental part, p. 2353 - 2362 (2009/04/05)
Hydrazones were prepared by condensation of carbocyclic and heterocyclic ketones with benzoyl- and tosylhydrazines. These hydrazones underwent nucleophilic addition with phosphite to provide efficiently (3- hydrazinopyrrolidin-3-yl)-, (3-hydrazinotetrahydrothiophen-3-yl)-, (3-hydrazinotetrahydrofuran-3-yl)-, and (1-hydrazinocyclopentyl)phosphonates. Cleavage of the hydrazine N-N bonds followed by acidic hydrolysis of the phosphonate functions of the (3-aminoheterocyclopentyl)phosphonates gave the new (3-aminopyrrolidin-3-yl)- and (3-aminotetrahydrothiophen-3-yl)phosphonic acids. This synthesis was achieved in a four-step sequence from the appropriate ketones. Georg Thieme Verlag Stuttgart.
