Abstract We report the synthesis of 4‐aryl‐2‐piperidone, 4‐arylpiperidine motifs, antituberculosis molecule Q203 (Telacebec) and its analogues. Direct lactamization β ‐C−H arylated N ‐phthaloyl δ ‐aminopentanoic acid carboxamides yielded 4‐aryl‐2‐piperidone (4‐aryl‐ ‐valerolactam) scaffolds. The required were assembled via Pd(II)‐catalyzed, 8‐aminoquinoline‐aided, sp 3 activation arylation meth...

In the present study, a new series of 2,6-diaryl-3-methyl-4-piperidones was synthesized by Mannich reaction (condensation) of ethyl-methyl ketone, substituted aromatic aldehydes and ammonium acetate. Oximes and thiosemicarbazone derivatives of 2,6-diaryl-3-methyl-4-piperidones were synthesized by reaction with hydroxylamine hydrochloride and thiosemicarbazide respectively. The chemical structur...

The first, highly enantioselective, copper/phosphoramidite-catalyzed conjugate addition of dialkylzinc reagents to N-substituted 2,3-dehydro-4-piperidones is described.

An efficient green chemistry approach to the synthesis of N-substituted piperidones and piperidines was developed and applied to the synthesis of 1-(2-pyridinylmethyl)-piperidin-4-one, 1, a key starting material for the synthesis of LY317615, an antiangiogenic agent currently under development at Eli Lilly and Company (Chart 1).(1) The general utility of this methodology, which presents signifi...

4-Piperidone and 4-alkyl piperidones react selectively with aromatic hydrocarbons in a mixture of trifluoromethanesulfonic acid (TFSA) and CH(2)Cl(2) to give linear polymers, while N-(2-phenethyl)piperidone undergoes self-polymerization to yield virtually 100%-hyperbranched polymer.

A general chemo-enzymatic approach to synthesize both enantioenriched trans-3-alkoxyamino-4-oxy-2-piperidones, which are important scaffold for various naturally occurring alkaloids, is reported. To this end, a selective transition-metal-free dual C−H oxidation of piperidines mediated by the TEMPO oxoammonium cation (TEMPO+) was used, followed enzymatic resolution corresponding alkoxyamino-2-pi...

1-[4-(2-Alkylaminoethoxy) phenylcarbonyl]-3,5-bis(arylidene)-4-piperidones are a novel class of potent cytotoxic agents. These compounds demonstrate low micromolar to submicromolar IC50 values against human Molt 4/C8 and CEM T-lymphocytes and murine leukemia L1210 cells. In this study, a comparative QSAR investigation was performed on a series of 3,5-bis (arylidene)-4-piperidones using differen...

Dengue is a severe mosquito-borne viral infection causing half a million deaths annually. Dengue virus NS2B/NS3 protease is a validated target for anti-dengue drug design. A series of hitherto unreported 3,5-bis(arylidene)-4-piperidones analogues 4a-4j were synthesized and screened in silico against DENV2 NS2B/NS3 protease to elucidate their binding mechanism and orientation around the active s...

The stereoselective synthesis of 3-substituted and 3,4-disubstituted piperidine and piperidin-2-one derivatives was achieved starting from 2-pyridone. After N-galactosylation and subsequent O-silylation, nucleophilic addition of organometallic reagents proceeded with high regioand stereoselectivity at 4-position. Substituents at position 3 were stereoselectively introduced by reaction of electr...

The relative configurations of alphaand beta-prodine have been discussed in a number of papers. Recently, ZIERISG, MOTCHANE and LEE^ have published an interpretation of the infra-red absorption spectra of the derived alcohols which they consider supports their original assignments, viz., cis methyl/ phenyl for alphaand trans methyl/phenyl for beta-prodine. BECKETT, CASY and WALKER,^,^ on the ot...