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Synthesis of 2-Substituted Quinolines From 2-Aminostyryl Ketones Using Iodide as a Catalyst

Synthesis of 2-Substituted Quinolines From 2-Aminostyryl Ketones Using Iodide as a Catalyst

So Young Lee, Jiye Jeon, Cheol-Hong Cheon

J Org Chem. 2018 May 4;83(9):5177-5186.

PMID: 29663808

Abstract:

A new protocol for the synthesis of 2-substituted quinolines from 2-aminostyryl ketones has been developed using iodide as a nucleophilic catalyst. Conjugate addition of iodide to 2-aminostyryl ketones yielded the corresponding β-iodoketones, which could have a conformation where the amino and carbonyl groups are proximal through free rotation about the Cα-Cβ single bond. Subsequent condensation between the amino and carbonyl groups followed by elimination of hydrogen iodide provided the corresponding quinolines, with regeneration of the iodide catalyst.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
LS7932266	2-Acetoxyphenylzinc iodide			Price

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