Practical direct synthesis of: N -aryl-substituted azacycles from N -alkyl protected arylamines using TiCl4and DBU

Van Hieu Tran, Minh Thanh La, Soosung Kang, Hee Kwon Kim

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8 Scopus citations


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.

Original languageEnglish
Pages (from-to)5008-5016
Number of pages9
JournalOrganic and Biomolecular Chemistry
Issue number26
StatePublished - 14 Jul 2020

Bibliographical note

Funding Information:
This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (2018R1D1A1B07047572).

Publisher Copyright:
© 2020 The Royal Society of Chemistry.


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