The three-component one-pot synthesis of highly functionalized piperidine derivatives was carried out by condensing 1,3-dicarbonyl compounds with aromatic aldehydes and aniline using a catalytic amount (10 mol%) of LaCl 3·7H 2O in methanol at room temperature. The main features of current protocol include easy work up, mild reaction conditions, good yields and high atom economy. © Springer Science+Business Media, LLC 2012.

Sathishkumar K

Department of Electrical Engineering

School of Electrical Engineering

Vellore Campus

Sathiyanarayanan K

Department of Chemistry

School of Advanced Sciences

Umamahesh B

Sathesh V

Ramachandran G

Vellore Institute of Technology (VIT) is a private university located in&nbsp;Tamil Nadu, India. Founded in 1984, as Vellore Engineering College, the institution offers 20 undergraduate, 34 postgraduate, four integrated and four research programs. It has campuses in Vellore, Amravati, Bhopal and Chennai.

VIT is one of the top ranked private universities in India according to NIRF, THE and QS Rankings.&nbsp;Govt. of India has recognized&nbsp;VIT, Vellore as an&nbsp;Institution of Eminence. This has allowed VIT to take independent quality initiatives and move up in world ranking.

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VIT University

Catalysis Letters

Acetic acid-promoted, one-pot synthesis of tetrahydropyridines has been developed under metal-catalyst-free conditions via a tandem reaction. High atom economy, good yield, simple procedure, no expensive column chromatography, shorter reaction time, and metal-free and mild reaction conditions are some of the important features of this protocol. The current methodology provides an alternative approach for not only highly substituted tetrahydropyridines (THPs) but also fully substituted tetrahydropyridines (FTHPs) in moderate to good yields. The plausible mechanism for the formation of THPs was greatly promoted by the H+ ion coming from acetic acid. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.] © 2014 Copyright Taylor and Francis Group, LLC.

Fulltext

Synthetic Communications

Metal-Free, One-Pot, Rapid Synthesis of Tetrahydropyridines Using Acetic Acid as Solvent and Catalyst at Room Temperature

A simple and efficient approach has been developed for the synthesis of highly substituted 3-amino-2-thiohydantoins using cyclododecanone as a protecting group and thiosemicarbazide, chloroacetic acid and substituted benzaldehyde as reactants. This high yielding (79-96%) protocol is a milder alternative to the traditional method that uses unprotected thiosemicarbazide. It was identified that the preferred pathway is the deprotection of 3-amino-2-thiohydantoins followed by the attack of chloroacetic acid on a secondary nitrogen with subsequent formation of the Knoevenagel product and its reaction with imine leading to the final product. © The Royal Society of Chemistry.

RSC Advances

Cyclododecanone as a recyclable protecting group for the synthesis of highly functionalized 3-amino-2-thiohydantoins from conventional starting materials

Tetrahedron Letters

Bismuth nitrate-catalyzed multicomponent reaction for efficient and one-pot synthesis of densely functionalized piperidine scaffolds at room temperature

Molecular Diversity

VCl3 catalyzed imine-based multicomponent reactions for the facile access of functionalized tetrahydropyridines and β-amino carbonyls

Tetrahedron

One-pot synthesis of highly diversified tetrahydropyridines by tandem condensation of aldehydes, amines, and β-ketoesters

Organic Letters

Synthesis of Enantiopure Substituted Piperidinesviaan Aziridinium Ring Expansion

Pyridine-mediated, one-pot, stereoselective synthesis of acyclic enaminones

LaCl3·7H2O as an Efficient Catalyst for One-Pot Synthesis of Highly Functionalized Piperidines via Multi-component Organic Reactions

Journal	Data powered by TypesetCatalysis Letters
Publisher	Data powered by TypesetSpringer Science and Business Media LLC
ISSN	1011-372X
Open Access	No