ACTION DES ENAMINES SUR LES MONOCHLOROPHOSPHINES: SYNTHESE DES Β-Cetophosphonates

Synthesis, Antimicrobial Activity and Molecular Docking Study of Novel α‐(Diphenylphosphoryl)‐ and α‐(Diphenylphosphorothioyl)cycloalkanone Oximes

“…The starting α-(diphenylphosphoryl)-and α-(diphenylphosphorothioyl)cycloalkanones 1 were easily prepared from the reaction of a cyclic enamine with P-chlorodiphenylphosphine in the presence of triethylamine, followed by oxidation or sulfurization and hydrolytic work-up, according to the reported procedure. [32][33][34] Reaction of compounds 1 with hydroxylamine hydrochloride, conducted in refluxing ethanol for 24 h in the presence of an equimolar quantity of potassium hydroxide, led to the desired α-(diphenylphosphoryl)-and α-(diphenylphosphorothioyl)cycloalkanone oximes 2. The isolated yield of the reaction ranges from 81 to 89% (Table 1).…”

“…The α-(diphenylphosphoryl)-and α-(diphenylphosphorothioyl)cycloalkanones 1 were prepared according to the procedure reported by Barkallah et al: [32] To a well stirred solution of enamine (1 mmol) and triethylamine (1.1 mmol) in dry acetonitrile (15 mL), maintained under an inert atmosphere (N2) and cooled at 0 °C, Pchlorodiphenylphosphine (1 mmol) in dry acetonitrile (3 mL) was added dropwise within 15 min. The resulting solution was warmed up to room temperature and stirred for 2 h. The reaction mixture was then treated with DMSO or sulphur as follows:…”

Direct Regio- and Diastereoselective Diphosphonylation of Cyclic Enamines: One-Pot Synthesis of α,α′-Bis(diphenylphosphoryl)- and α,α′-Bis(diphenylphosphorothioyl)cycloalkanones

“…Initially, the reaction was tested with 1 equiv Ph2PCl and 1.1 equiv Et3N in different solvents, in order to improve the experimental protocol for the formation of the monophosphonylated products 22,23 and to ascertain if the desired diphosphonylated compounds could be detected in these conditions. The reaction provided mainly the monophosphonylated product 3a with trace amounts of the ,'-bis(diphenylphosphoryl)cyclohexanone 2a ( Table 1, entries 1-6).…”

“…[11][12][13][14][15][16] Some of their fluorescent complexes with lanthanum group metals are also used as light-emitting components in organic light-emitting diodes. 17 Within our ongoing studies on the reactivity and potential synthetic applications of imines and enamines [18][19][20][21] and inspired by the reaction of enamines with chlorophosphines which leads to -phosphonylcycloalkanones, 22,23 we anticipated that treatment of cyclic enamines with excess P-chlorodiphenylphosphine, followed by oxidation or sulfurization and hydrolytic work-up, would allow a straightforward approach to unprecedented symmetrical ,'-bis(diphenylphosphoryl)-and ,'-bis(diphenylphosphorothioyl)-cycloalkanones. Being tridentate ligands, these compounds might show enhanced complexing properties with regard to their -phosphonylketone homologues.…”

Experimental and computational investigation of Z/E isomerism, X-ray crystal structure and molecular docking study of (2-(hydroxyimino)cyclohexyl)diphenylphosphine sulfide, a potential antibacterial agent

“…The starting 2-(diphenylphosphorothioyl)cyclohexanone ( 1 ) was easily prepared from the reaction of a cyclic enamine [1morpholinocyclohexene] with P -chlorodiphenylphosphine in the presence of triethylamine, followed by sulfurization and hydrolytic work-up, according to the reported procedure [27] . Reaction of compound ( 1 ) with hydroxylamine hydrochloride, performed in refluxing ethanol for 24 h in the presence of an equimolar amount of potassium hydroxide, led to the desired α-(diphenylphosphorothioyl)cyclohexanone oxime ( 2 ) in 87% isolated yield ( Scheme 1 ).…”