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

Nicolas Rabasso; Antoine Fadel

doi:10.1055/s-2008-1067130

PAPER

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

Nicolas Rabasso, Antoine Fadel*
Laboratoire de Synthèse Organique et Méthodologie, UMR 8182, Institut de Chimie Moléculaire et des Matériaux d’Orsay, Bât. 420, Univ Paris-Sud, 91405 Orsay, France
Fax: +33(1)69156278; e-Mail: antfadel@icmo.u-psud.fr;

Abstract

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Abstract

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.

Key words

phosphonic acids - heterocycles - amines - cucurbitine analogue - nucleophilic additions

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References

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