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Practical direct synthesis of N-aryl-substituted azacycles from N-alkyl protected arylamines using TiCl4 and DBU

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Abstract

A novel transformation of N-alkyl protected arylamines and cyclic ethers into N-aryl substituted azacycles is described. Alkyl groups have been used for the protection of amines in organic syntheses. In this synthesis, N-alkyl protected arylamines were reacted with cyclic ethers in the presence of TiCl4 and DBU, crucial reagents affording five- and six-membered azacycles. In particular, utilization of the novel TiCl4/DBU-mediated reaction allows various N-alkyl protected arylamines such as N-methyl-, N-ethyl-, N-isopropyl, and N-tert-butyl arylamines to be readily converted into N-aryl substituted azacycles in high yields. This practical approach using various N-alkyl arylamines leads to the efficient preparation of azacycles.

Graphical abstract: Practical direct synthesis of N-aryl-substituted azacycles from N-alkyl protected arylamines using TiCl4 and DBU

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Article information


Submitted
28 Apr 2020
Accepted
12 Jun 2020
First published
12 Jun 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Paper

Practical direct synthesis of N-aryl-substituted azacycles from N-alkyl protected arylamines using TiCl4 and DBU

V. H. Tran, M. T. La, S. Kang and H. Kim, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/D0OB00880J

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