Functionalized tetrahydroisoquinolines are convenient precursors for the construction of numerous heterocyclic compounds of therapeutic importance. In this paper we have illustrated an efficient synthesis of highly substituted tetrahydroisoquinolines from 2H-pyran-2-ones via nucleophile-mediated ring transformation with tert-butyl-4-oxopiperidine-1-carboxylate followed by acid-mediated cleavage of the tert-butyloxycarbonyl group. The products were achieved smoothly in high yields with flexibility of various substituents.

Fateh Veer Singh

Chemistry

School of Advanced Sciences

Chennai Campus

Kole P.B

Fulltext

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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Versatile Synthesis of Functionalized Tetrahydroisoquinolines by Ring Transformation of 2H-Pyran-2-ones

Australian Journal of Chemistry

An efficient metal-free approach for the synthesis of functionalized biaryl-cored diarylmethanes is described by the ring transformation of 2H-pyran-2-ones using 4-phenylbutan-2-one as carbanion source. Moreover, 2H-pyran-2-ones were reacted with 1,3-diphenylacetone in the presence of base to achieve functionalized teraryl-cored diarylmethanes. All the ring transformation reactions were performed under mild reaction conditions to afford the biaryl- and teraryl-cored reaction products in high yields.

Synthesis

Metal-Free Synthesis of Biaryl- and Teraryl-Cored Diarylmethanes by Ring Transformation of 2H-Pyran-2-ones

A metal-free, ultrasound-assisted approach for the synthesis of highly functionalized 2-tetralones in high yields is described. The process involves ring transformation of 2H-pyran-2-ones with the spirocyclic ketone 1,4-cyclohexandione monoethylene ketal to yield spiro­cyclic ketals and subsequent acid-mediated hydrolysis. This protocol is free from any organometallic reagents, is economical and tolerates a wide range of functional groups.

A Metal-Free Approach for the Synthesis of 2-Tetralones via Carbanion-Induced Ring Transformation of 2H-Pyran-2-ones

Clinical Toxicology

The stimulant higenamine in weight loss and sports supplements

Tetrahedron

Lewis acid-catalyzed [3+3] cycloadditions of donor‒acceptor aziridines with N,N-dialkyl-3-vinylanilines via carbon-carbon bond cleavage

ACS Chemical Neuroscience

Isolation and Sequencing of Salsolinol Synthase, an Enzyme Catalyzing Salsolinol Biosynthesis

Journal	Australian Journal of Chemistry
Publisher	CSIRO Publishing
ISSN	0004-9425
Open Access	Yes