Facile Metal-Free Direct Transformation of N-Allyl- and tert-Butyl-Protected Arylamines to Azacycles Using Phosphoryl Chloride and TBD

Submitting author affiliation:
Jeonbuk National University, Jeonju, Korea, Republic of

Beilstein Arch. 2020, 2020123. https://doi.org/10.3762/bxiv.2020.123.v1

Published 28 Oct 2020

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A novel synthetic approach to the preparation of N-aryl substituted azacycles from N-allyl and N-tert-butyl protected arylamines is described. In this preparation, a metal free reagent system utilizing POCl3 and TBD proved to be an important contributor for reactions of N-allyl- and tert-butyl-protected aryamines with cyclic ethers to generate the target azacycles. This protocol provides a practical approach to high yield, direct synthesis of N-aryl substituted five-membered and six-membered azacycles from N-allyl arylamines and N-tert-butyl arylamines

Keywords: Azacycles; N–allyl arylamines; Ntert-butyl arylamines; Direct Transformation; Cyclic ethers.

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Tran, V. H.; Hong, W. P.; Kim, H.-K. Beilstein Arch. 2020, 2020123. doi:10.3762/bxiv.2020.123.v1

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