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Cycloaddition/aromatization sequence for the synthesis of 2,3-disubstituted benzenephosphonates

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Villemin, Elise [UCL] Marchand-Brynaert, Jacqueline [UCL]

The [4+2] cycloaddition of diethyl 1-phosphonobuta-1,3-diene with tetracyanoethylene, (E)-1,4-diphenylbut-2-ene-1,4-dione, N-phenylmaleimide, and dialkyl acetylenedicarboxylates is described. For the last two cases, treatment of the cycloadducts with nitrobenzene and a palladium catalyst allows the aromatization. Selective deprotections lead to phthalimide/phthalate derivatives with an ortho-phosphonic acid function. © Georg Thieme Verlag Stuttgart · New York.

Document type Article de périodique (Journal article) – Article de recherche
Publication date 2012
Language Anglais
Journal information "Synthesis (Germany)" - Vol. 44, no.12, p. 1923-1927 (2012)
Peer reviewed yes
Publisher Thieme
issn 0039-7881
Publication status Publié
Affiliation UCL - SST/IMCN/MOST - Molecules, Solids and Reactivity
Keywords Bicyclic compounds ; Dialkyl acetylenedicarboxylates ; Diels-Alder reaction ; N-phenylmaleimide ; Palladium catalyst ; Phthalimide ; Tetracyanoethylene ; Cycloaddition ; Hydrolysis ; Olefins ; Phosphorus ; Carboxylic acids ; Carboxylic acids ; 1,3 dioxo 2 phenylisoindolin 4 yl 4 phosphonic acid ; 1,4 diphenylbut 2 ene 1,4 dione ; 2 phosphonic acid ; 2,3 bis(methoxycarbonyl)phenylphosphonic acid ; 3 phosphonophthalic acid ; Alkadiene ; Benzenephosphonic acid derivative ; Dialkyl acetylenedicarboxylic acid ; Diethyl 1 phosphonobuta 1,3 diene ; Cycloaddition ; Diethyl 1,3 dioxo 2 phenylisoindolin 4 yl 4 phosphonic acid ; Diethyl 5,5,6,6 tetracyanocyclohex 2 enylphosphonic acid ; Diethyl 5,6 (dibenzoyl)cyclohex 2 en 1 ylphosphonic acid ; Dimethyl 3 (diethoxyphosphoryl)cyclohexa 1,4 diene 1,2 dicarboxylic acid ; Dimethyl 3 (diethoxyphosphoryl)phthalic acid ; N phenylmaleimide ; Nitrobenzene ; Palladium ; Phosphonic acid derivative ; Phthalimide derivative ; Diels-Alder reaction ; Tetracyanoethylene ; Unclassified drug ; Aromatization ; Article ; Catalyst ; Chemical analysis ; Chemical structure ; Controlled study ; Cycloaddition ; Deprotection reaction ; Hydrolysis ; Synthesis ; Phosphorus ; Acid function ; Bicyclic compounds ; Cycloadducts
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Bibliographic reference Villemin, Elise ; Marchand-Brynaert, Jacqueline. Cycloaddition/aromatization sequence for the synthesis of 2,3-disubstituted benzenephosphonates. In: Synthesis (Germany), Vol. 44, no.12, p. 1923-1927 (2012)
Permanent URL http://hdl.handle.net/2078.1/124625