Reactions of Azovinylphosphonates with Nucleophilic Alkenes and Heterocycles: Synthesis of Tetrahydropyridazine-3-phosphonate and 2-Substituted-1-hydrazonoethylphosphonate Derivatives

Authors: Lemos, Americo; Lopes, Marta

Source: Phosphorus, Sulfur, and Silicon and the Related Elements, Volume 183, Number 11, November 2008 , pp. 2882-2890(9)

Publisher: Taylor and Francis Ltd

Buy & download fulltext article:

Price: $56.94 plus tax (Refund Policy)

Abstract:

Transient azovinylphosphonates, generated in situ by base induced dehydrohalogenation of the corresponding 2-bromo- and 2-chloro-acetylphosphonate- tertbutoxycarbonyl hydrazones are intercepted by electron rich alkenes and heterocycles in hetero Diels-Alder reactions, producing tetrahydopyridazine-3-phosphonates or open chain α-hydrazono phosphonates.

Keywords: α-hydrazonophosphonates; 3-phosphono-1,2-diaza-1,3-butadienes; azovinylphosphonates; addition-elimination; cycloaddition; tetrahydropyridazine-3-phosphonates

Document Type: Research article

DOI: http://dx.doi.org/10.1080/10426500802028393

Affiliations: 1: CIQA, Departamento de Quimica, Bioquimica e Farmacia, Faculdade de Ciencias e Tecnologia, Universidade do Algarve, Faro, Portugal

Publication date: 2008-11-01