Copper(i) iodide-catalyzed synthesis of N,N′-disubstituted guanidines from n-substituted cyanamides

Cian Jhe Zeng; Chia Jung Chen; Chih Wei Chang; Hui Ting Chen; Tun Cheng Chien

doi:10.1071/CH14197

Copper(i) iodide-catalyzed synthesis of N,N′-disubstituted guanidines from n-substituted cyanamides

Cian Jhe Zeng
, Chia Jung Chen
, Chih Wei Chang
, Hui Ting Chen^*
, Tun Cheng Chien

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1134-1137
Number of pages	4
Journal	Australian Journal of Chemistry
Volume	67
Issue number	7
DOIs	https://doi.org/10.1071/CH14197
Publication status	Published - 2014

ASJC Scopus subject areas

General Chemistry

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title = "Copper(i) iodide-catalyzed synthesis of N,N′-disubstituted guanidines from n-substituted cyanamides",

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.",

author = "Zeng, \{Cian Jhe\} and Chen, \{Chia Jung\} and Chang, \{Chih Wei\} and Chen, \{Hui Ting\} and Chien, \{Tun Cheng\}",

note = "Funding Information: This work was supported by Research Grants 102{\textendash}2113-M-003{\textendash}004-and 102{\textendash}2113-M-037{\textendash}003-from Ministry of Science and Technology, Taiwan, and NTNU100-D-06 from National Taiwan Normal University. We also thank Professor Choon Hong Tan (Nanyang Technological University) for his helpful discussion and Mr Ting-Shen Kuo (National Taiwan Normal University) for his assistance with X-ray crystallographic analysis.",

year = "2014",

doi = "10.1071/CH14197",

language = "English",

volume = "67",

pages = "1134--1137",

journal = "Australian Journal of Chemistry",

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T1 - Copper(i) iodide-catalyzed synthesis of N,N′-disubstituted guanidines from n-substituted cyanamides

AU - Zeng, Cian Jhe

AU - Chen, Chia Jung

AU - Chang, Chih Wei

AU - Chen, Hui Ting

AU - Chien, Tun Cheng

N1 - Funding Information: This work was supported by Research Grants 102–2113-M-003–004-and 102–2113-M-037–003-from Ministry of Science and Technology, Taiwan, and NTNU100-D-06 from National Taiwan Normal University. We also thank Professor Choon Hong Tan (Nanyang Technological University) for his helpful discussion and Mr Ting-Shen Kuo (National Taiwan Normal University) for his assistance with X-ray crystallographic analysis.

PY - 2014

Y1 - 2014

N2 - 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.

AB - 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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DO - 10.1071/CH14197

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AN - SCOPUS:84904409373

SN - 0004-9425

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JO - Australian Journal of Chemistry

JF - Australian Journal of Chemistry

IS - 7

ER -

Copper(i) iodide-catalyzed synthesis of N,N′-disubstituted guanidines from n-substituted cyanamides

Abstract

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