18350-44-2Relevant academic research and scientific papers
New carbanionic access to 3-vinylindoles and 3-vinylbenzofurans
Le Strat, Frederic,Maddaluno, Jacques
, p. 2791 - 2793 (2002)
(Matrix presented) A simple route to 3-vinylbenzofurans, 3-vinylfuropyridines, and 3-vinylindoles from readily accessible acetylenic precursors is described. A standard halogen-lithium exchange triggers an irreversible addition on the triple bond, accordi
Copper-Catalyzed Regiospecific and 1,2-Regioselective Cyclopropanation of (1 Z)-1-Amino- and (1 Z)-1-Oxy-1,3-butadienyl Derivatives
Tayama, Eiji,Saito, Shun
, p. 1880 - 1884 (2015/08/06)
The copper-catalyzed regiospecific and 1,2-regioselective cyclopropanation of (1Z)-1-amino- and (1Z)-1-oxy-1,3-butadienyl derivatives, which could be prepared by Z-stereoselective 1,4-elimination with α-aryl diazoesters was successfully demonstrated. This successful regiospecific protocol enabled the preparation of the corresponding 1-amino- and 1-oxy-2-vinylcyclopropane derivatives as almost single stereoisomers.
An efficient synthesis of epoxydiynes and a key fragment of Neocarzinostatin chromophore
Baker,Thominet,Britton,Caddick
, p. 45 - 48 (2007/10/03)
(Chemical Equation Presented) A key structural feature of the Neocarzinostatin chromophore is a reactive epoxydiyne. We present here a new method for the preparation of epoxydiynes by the addition of an allenyl zinc bromide to a propargylic ketone.
Synthetic strategies to epoxydiynes and a key synthon of the neocarzinostatin chromophore
Thominet, Olivier,Baker, James R.,Britton, Hugh,Etheridge, Zac C.,Soscia, Marco G.,Caddick, Stephen
, p. 3703 - 3712 (2008/09/21)
We present herein our recent efforts towards the synthesis of epoxydiynes which represent an unusual structural feature of the neocarzinostatin chromophore. A number of different routes to these epoxydiynes have been explored with varying success. Ultimately a concise and convergent approach was developed, which involved the addition of an allenyl zinc bromide to propargylic ketones/aldehydes followed by epoxide formation. This new protocol enabled us to synthesise a fully elaborated epoxydiyne which will find application for our studies towards the total synthesis of the NCS chromophore. The Royal Society of Chemistry.
Solvent and substituent effects on conjugated eliminations in propargylic systems
Le Strat, Frédéric,Maddaluno, Jacques
, p. 5367 - 5371 (2007/10/03)
The deprotonation of 4-methoxy-but-2-ynal diethyl acetal by n- butyllithium induces an acetylenic-allenic isomerization (in diethylether) or a conjugated elimination reaction (in THF), providing the corresponding 1,4- dialkoxycumulene. An allenyllithium, that has been trapped as an allenylstannane, is proposed to be a common intermediate to both pathways. Also, the deprotonation of 4-dialkylamino-but-2-ynal diethyl acetals in the same conditions affords a mixture of (E) and (Z) aminocrotonates of which formation can be explained by a chemioselective removal of the acetalic proton leading to an intermediate allenyllithium that has equally been trapped by stannylation. (C) 2000 Elsevier Science Ltd.
Dihydropyridazinones, pyridazinones and related compounds as fungicides
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, (2008/06/13)
This invention relates to substituted dihydropyridazinones, pyridazinones and related compounds, of the formula STR1 wherein A, Q, D and R1 are as defined within, compositions containing these compounds and methods of controlling agricultural and mammalian fungal diseases.
Synthese de composes acetyleniques &α,&α'-difonctionnels utilisables dans l'inhibition selective de la croissance de cellules transformees
Raffin, Catherine,Bernard, Didier,Fournet, Guy,Gore, Jacques,Chantepie, Jacqueline,Quash, Gerard
, p. 152 - 172 (2007/10/02)
En fonction de diverses donnees, il apparait que le taux intracellulaire du malondialdehyde (MDA), inhibiteur de la croissance cellulaire, puisse etre regule par cinq enzymes: la desacetylase, la diamine oxydase, l'aldehyde reductase (AIR) et les aldehydes deshydrogenases (AIDH1 et AIDH2).Sur la base de resultats anterieurs du groupe, divers composes acetyleniques α,α'-difonctionnels ont ete supposes pouvoir diminuer selectivement la croissance des cellules transformees en inhibant, soit l'AIR, soit les AIDH et en augmentant de ce fait le taux intracellulaire de MDA.Dix composes ont ete selectionnes et synthetises: certains d'entre eux possedent les proprietes attendues et ont montre une activite et une selectivite remarquables lors de tests in vitro.Bien que ces proprietes ne se soient pas traduites par une activite antitumorale in vivo, cette etude montre que cette voie constitue une approche dans la conception d'agents pour des therapies antitumorales.
4-FLUORO-2-BUTYNAL: PREPARATION AND SOME EXAMPLES OF DIENOPHILIC PROPERTIES
Khanous, A.,Gorgues, A.,Cousseau, J.
, p. 401 - 408 (2007/10/02)
4-Fluoro-2-butynal FCH2CCCHO (5) is prepared in good yield by formolysis of the corresponding fluoro-acetal FCH2CCH(OC2H5)2 (4).The dienophilic properties of (5) are investigated towards 2,3-dimethyl-1,3-butadiene (6), cyclopentadiene (7) and 1,3-cyclohex
