Tetraethyl vinylidenebisphosphonate: A versatile synthon for the preparation of bisphosphonates

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Tetraethyl vinylidenebisphosphonate is a versatile synthetic intermediate that allows access to a variety of highly functionalized compounds bearing the bisphosphonic moiety. As an electron-deficient alkene, this compound is able to undergo conjugate addition with a variety of reagents including str...

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Autor principal: Rodriguez, J.B
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Publicado: Georg Thieme Verlag 2014
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024 7 |2 scopus  |a 2-s2.0-84899620311 
024 7 |2 cas  |a azide, 12596-60-0, 14343-69-2; azomethine ylide, 107081-71-0, 1761-67-7, 176903-89-2; phosphorus, 7723-14-0 
040 |a Scopus  |b spa  |c AR-BaUEN  |d AR-BaUEN 
030 |a SYNTB 
100 1 |a Rodriguez, J.B. 
245 1 0 |a Tetraethyl vinylidenebisphosphonate: A versatile synthon for the preparation of bisphosphonates 
260 |b Georg Thieme Verlag  |c 2014 
270 1 0 |m Rodriguez, J.B.; Departamento de Química Orgánica and UMYMFOR (CONICET-FCEyN), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, C1428EHA, Buenos Aires, Argentina; email: jbr@qo.fcen.uba.ar 
506 |2 openaire  |e Política editorial 
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520 3 |a Tetraethyl vinylidenebisphosphonate is a versatile synthetic intermediate that allows access to a variety of highly functionalized compounds bearing the bisphosphonic moiety. As an electron-deficient alkene, this compound is able to undergo conjugate addition with a variety of reagents including strong nucleophiles, such as organometallic reagents and enolates, as well as very mild nucleophiles, such as amines, mercaptans and alcohols. The title compound also possesses the ability to behave as a dipolarophile or dienophile in 1,3-dipolar cycloadditions or Diels-Alder reactions, giving rise to five- or six-membered rings containing the bisphosphonic unit. In summary, tetraethyl vinylidenebisphosphonate is a very useful synthon to have at hand for straightforward syntheses of bisphosphonate derivatives of diverse structures. This bisphosphonate moiety has proven to be very important to impart important pharmacological action. 1 Introduction 2 General Reactivity 3 Michael Addition Reactions 3.1 Reaction with Organometallic Reagents 3.2 Reaction with Mercaptans and Amines 3.3 Reaction with Phosphorus-Containing Nucleophiles 3.4 Epoxidation, Loss of a Phosphonate Unit and Rearrangement Reactions 3.5 Michael Reactions with Enolates 4. Cycloaddition Reactions 4.1 Diels-Alder Reactions 4.2 1,3-Dipolar Cycloadditions 4.2.1 Reaction with Diazo Compounds 4.2.2 Reaction with Nitrones 4.2.3 Reaction with Nitrile Oxides 4.2.4 Grigg Azomethine Ylide Cyclizations 4.2.5 Reaction with Azides 5 Concluding Remarks. © Georg Thieme Verlag Stuttgart, New York.  |l eng 
593 |a Departamento de Química Orgánica and UMYMFOR (CONICET-FCEyN), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, C1428EHA, Buenos Aires, Argentina 
690 1 0 |a 1 3-DIPOLAR CYCLOADDITIONS 
690 1 0 |a BISPHOSPHONATES 
690 1 0 |a MICHAEL ADDITIONS 
690 1 0 |a TETRAETHYL VINYLIDENE BISPHOSPHONATE 
690 1 0 |a AMINES 
690 1 0 |a CHEMICAL COMPOUNDS 
690 1 0 |a CYCLOADDITION 
690 1 0 |a NITROGEN OXIDES 
690 1 0 |a NUCLEOPHILES 
690 1 0 |a OLEFINS 
690 1 0 |a ORGANOMETALLICS 
690 1 0 |a 1 ,3-DIPOLAR CYCLOADDITIONS 
690 1 0 |a BISPHOSPHONATES 
690 1 0 |a CYCLOADDITIONS 
690 1 0 |a FUNCTIONALIZED COMPOUNDS 
690 1 0 |a MICHAEL ADDITION REACTIONS 
690 1 0 |a MICHAEL ADDITIONS 
690 1 0 |a REARRANGEMENT REACTIONS 
690 1 0 |a SYNTHETIC INTERMEDIATES 
690 1 0 |a ADDITION REACTIONS 
690 1 0 |a AMINE 
690 1 0 |a AZIDE 
690 1 0 |a AZOMETHINE YLIDE 
690 1 0 |a BISPHOSPHONIC ACID DERIVATIVE 
690 1 0 |a NITRILE OXIDE 
690 1 0 |a NITRONE DERIVATIVE 
690 1 0 |a PHOSPHONIC ACID DERIVATIVE 
690 1 0 |a PHOSPHORUS 
690 1 0 |a TETRAETHYL VINYLIDENEBISPHOSPHONATE 
690 1 0 |a THIOL 
690 1 0 |a UNCLASSIFIED DRUG 
690 1 0 |a CHEMICAL STRUCTURE 
690 1 0 |a CONCENTRATION (PARAMETERS) 
690 1 0 |a CYCLIZATION 
690 1 0 |a CYCLOADDITION 
690 1 0 |a ENANTIOSELECTIVITY 
690 1 0 |a EPOXIDATION 
690 1 0 |a MICHAEL ADDITION 
690 1 0 |a OXIDATION REDUCTION REACTION 
690 1 0 |a PHYSICAL CHEMISTRY 
690 1 0 |a REVIEW 
690 1 0 |a STEREOCHEMISTRY 
690 1 0 |a STRUCTURE ANALYSIS 
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