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

  1. Van Hieu Tran,
  2. Wan Pyo Hong and
  3. Hee-Kwon KimORCID Logo

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

  • Preprint

Abstract

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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When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

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

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