Synlett 2016; 27(07): 1121-1127
DOI: 10.1055/s-0035-1561201
letter
© Georg Thieme Verlag Stuttgart · New York

One-Pot Synthesis of C 2 Symmetric and Asymmetric N,N′,N′′-Substituted Guanidines from Aryl Isothiocyanates and Amines

Sirilak Wangngae
Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand   Email: wongp2577@gmail.com
,
Mookda Pattarawarapan
Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand   Email: wongp2577@gmail.com
,
Wong Phakhodee*
Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand   Email: wongp2577@gmail.com
› Author Affiliations
Further Information

Publication History

Received: 05 November 2015

Accepted after revision: 06 December 2015

Publication Date:
05 January 2016 (online)


Abstract

Highly substituted guanidines were conveniently prepared through a one-pot reaction between aryl isothiocyanates and amines mediated by the Ph3P–I2/Et3N system. The C 2-symmetric N,N′,N′′-substituted guanidines were readily accessed using a 1:2 molar ratio of an aryl isothiocyanate and an amine; while sequential addition of two different amines in equimolar ratios gave rise to asymmetric derivatives. Both primary and secondary amines were found to react preferentially with electron-deficient aryl isothiocyanates, rapidly providing guanidines in good yields under mild conditions.

Supporting Information

 
  • References and Notes

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