Synthetic application of fluorinated vinamidinium salts: Synthesis of fluorinated 1,3-butadienylphosphonates by the reaction with Horner–Wadsworth–Emmons reagents

Synthèses et applications des oxophosphonates en chimie organique

“…Pour des chaı ˆnes plus longues, Arimitsu et coll. [48] ont constate ´que l'hydrolyse a `tempe ´rature ambiante des 1,3-butadie ´nylphosphonates par une solution a 10% de HCl, conduit aux oxophosphonates fluore ´s a,b-insature ´s avec de bons rendements (Sche ´ma 33).…”

“…De ´rive ´s de la pyridine. L'acce `s aux pyridines fonctionnelles est possible en traitant le die ´thyl-1-ace ´tyl-4-(dime ´thylamino)-3-fluoro-(1E,3Z)-butadie ´nyl-phosphonate [48] par une solution aqueuse de NH 3 a `25%. Cette ope ´ration se de ´roule a `tempe ´rature mode ´re ´e Dans le but de synthe ´tiser le mode `le annele ´dans la se ´rie des quinolie ´nes, le die ´thyl (2-oxopropyl)-phosphonate est condense ´avec l'imine de ´rive ´e de 2-amino-4,5-dime ´thoxybenzalde ´hyde selon la modification de Borsche de la re ´action de Friedlander [91].…”

Reaction of hydroxylated naphtoquinones/antraquinones with pentafluoropyridine

“…In pharmacology and medicinal researches, it is common to substitute hydrogen with fluorine atom for increasing the lipophilicity and the biological activity of drugs (Anatoliy et al 2009). Various multi-functional pyridine derivatives and the construction of new heterocyclic drug systems could be accessed from the high electron efficiency of pentafluoropyridine and appropriate nucleophile in simple reaction conditions (Satoru et al 2006; Cindy et al 2010). The reactions of pentafluoropyridine with nucleophiles occurs in the most activated 4-position of pentafluoropyridine to give products arising from the substitution of fluorine, located para to ring nitrogen to give a range of 4-substituted tetrafluoropyridine systems (Mark et al 2012).…”

Wittig--Horner reagents: powerful tools in the synthesis of 5-and 6-heterocyclic compounds; shedding light on their application in pharmaceutical chemistry

“…BuOK gave the 1,3-butadienylphosphonates 121 in good yields. The latter compound was treated with ammonia to afford pyridin-3-ylphosphonate 122 in 60% yield (Scheme 32) 45. …”