Copper(i) Iodide-Catalyzed Synthesis of N,N′-Disubstituted Guanidines from N-Substituted Cyanamides*
Cian-Jhe Zeng A , Chia-Jung Chen A , Chih-Wei Chang A , Hui-Ting Chen B C and Tun-Cheng Chien A C
+ Author Affiliations
- Author Affiliations
A Department of Chemistry, National Taiwan Normal University, Taipei 11677, Taiwan.
B Department of Fragrance and Cosmetic Science, Kaohsiung Medical University, Kaohsiung 80708, Taiwan.
C Corresponding authors. Email: htchen@kmu.edu.tw; tcchien@ntnu.edu.tw
Australian Journal of Chemistry 67(7) 1134-1137 https://doi.org/10.1071/CH14197
Submitted: 1 April 2014 Accepted: 2 June 2014 Published: 30 June 2014
Abstract
A facile and effective synthesis of N-alkyl-N′-arylguanidines was accomplished by the reaction of N-arylcyanamides with various primary and secondary alkylamines, under the catalysis of copper(i) iodide and Xantphos in DMF. This methodology provides a direct access to versatile N,N′-disubstituted guanidine derivatives from N-arylcyanamides that can be readily prepared from the corresponding nitriles via Tiemann rearrangement.
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