The von Braun Reaction Applied to Azetidines
- 22 December 2017
- journal article
- research article
- Published by Wiley in European Journal of Organic Chemistry
- Vol. 2017 (47) , 7195-7201
Abstract
The von Braun reaction (the reaction of cyanogen bromide with tertiary amines) was applied to a series of functionalized N‐alkyl‐substituted azetidines. This reaction mainly led to the cleavage of the strained four‐membered ring to produce 3‐bromo N‐alkyl cyanamides in good yields with variable regioselectivity. The resulting cyanamide products were then employed as original building blocks for the synthesis of nitrogen heterocycles.Keywords
Funding Information
- CNRS
- University of Versailles St Quentin en Yvelines
This publication has 45 references indexed in Scilit:
- 2‐Cyanoazetidines and Azetidinium Ions: Scaffolds for Molecular DiversityEuropean Journal of Organic Chemistry, 2013
- Preparation and Synthetic Applications of AzetidinesHETEROCYCLES, 2012
- Synthesis of 3-Methoxyazetidines via an Aziridine to Azetidine Rearrangement and Theoretical Rationalization of the Reaction MechanismThe Journal of Organic Chemistry, 2011
- Asymmetric Synthesis of α-Chloro-β-amino-N-sulfinyl Imidates as Chiral Building BlocksThe Journal of Organic Chemistry, 2011
- Novel Syntheses of Azetidines and AzetidinonesChemical Reviews, 2008
- Convenient Synthesis oftrans-β-Amino Carboxylic Esters with an Azetidine Skeleton via Rearrangement of β,γ-Aziridino α-amino EstersOrganic Letters, 2007
- Synthesis of Chiral Non Racemic AzetidinesMini-Reviews in Organic Chemistry, 2004
- A convenient synthesis of 3-alkoxyazetidinesTetrahedron, 1995
- Synthesis of azetidines from β-chloro iminesTetrahedron, 1988
- A novel synthesis of 2-cyano-3,3-dimethylazetidinesJournal of the Chemical Society, Chemical Communications, 1985