A convenient one pot synthesis of highly substituted piperidines through a Michael addition-aldol cyclization sequence

An efficient method for the synthesis of N,N-bis(phenacyl)anilines was developed via smooth condensation of anilines with α-bromoacetophenones in the presence of sodium carbonate as acid acceptor and polyethylene glycol 400 (PEG 400) as catalyst at room temperature under solvent-free conditions by using 350 W ultrasound irradiation. In addition to experimental simplicity, the main advantages of the procedure are mild conditions, short reaction times (30–45 min), and high yields (73–83 %).Graphical Abstract

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Ultrasound-mediated synthesis of N,N-bis(phenacyl)aniline under solvent-free conditions

Jianguo

Shi

Liu

et al. 2013

Monatsh Chem

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Sulfated titania (TiO2-SO42−) as an efficient and reusable solid acid catalyst for the multi-component synthesis of highly functionalized piperidines

Geetha

Thangamani

Valliappan

et al. 2020

Chemical Data Collections

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Organometallic Enantiomeric Scaffolding: A Strategy for the Enantiocontrolled Construction of Regio- and Stereodivergent Trisubstituted Piperidines from a Common Precursor

2011

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Reported herein is a general and efficient method to construct 2,3,6-trisubstituted piperidines in a substituent-independent fashion. From the high enantiopurity organometallic scaffold (−)-Tp(CO)2[(η-2,3,4)-(1S, 2S)-1-benzyloxycarbonyl-5-oxo-5,6-dihydro-2H-pyridin-2-yl)molybdenum (Tp = hydridotrispyrazolylborato), a variety of TpMo(CO)2-based 2,3,6-trifunctionalized complexes of the (η-3,4,5-dihydropyridinyl) ligand were easily obtained in 5 steps through a sequence of highly regio- and stereospecific metal-influenced transformations (15 examples). From the 2,3,6-trifunctionalized molybdenum complexes, either 2,6-cis-3-trans or 2,3,6-cis systems were selectively obtained through the choice of an appropriate stereodivergent demetalation protocol. The potential of this strategy in synthetic chemistry was demonstrated by the short total synthesis of four natural and one non-natural alkaloids: indolizidines (±)-209I and (±)-8-epi-219F in the racemic series, and enantiocontrolled syntheses of (−)-indolizidine 251N, (−)-quinolizidine 251AA, and (−)-dehydroindolizidine 233E.

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A convenient one pot synthesis of highly substituted piperidines through a Michael addition-aldol cyclization sequence

Abstract: A neat and rapid procedure is reported for the synthesis of a variety of (2-aroyl-5-hydroxy-1,3,5-triaryl-4-piperidyl)(aryl)methanone (3a-3g) by the condensation of 2-[(2-oxo-2-arylethyl)anilino]-1-aryl-1-ethanones 1 with different arylidene acetophenone 2 under microwave irradiation.

Cited by 9 publications

References 14 publications

Ultrasound-mediated synthesis of N,N-bis(phenacyl)aniline under solvent-free conditions

Ultrasound-mediated synthesis of N,N-bis(phenacyl)aniline under solvent-free conditions

Sulfated titania (TiO2-SO42−) as an efficient and reusable solid acid catalyst for the multi-component synthesis of highly functionalized piperidines

Organometallic Enantiomeric Scaffolding: A Strategy for the Enantiocontrolled Construction of Regio- and Stereodivergent Trisubstituted Piperidines from a Common Precursor

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