Synlett 2014; 25(09): 1302-1306
DOI: 10.1055/s-0033-1341080
letter
© Georg Thieme Verlag Stuttgart · New York

Direct Guanylation of Amino Groups by Cyanamide in Water: Catalytic Generation and Activation of Unsubstituted Carbodiimide by Scandium(III) Triflate

Kazuki Tsubokura
a  Biofunctional Synthetic Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan   Fax: +81(48)4679379   Email: kotzenori@riken.jp
b  School of Advanced Science and Engineering, Department of Chemistry and Biochemistry, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan
,
Takayuki Iwata
a  Biofunctional Synthetic Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan   Fax: +81(48)4679379   Email: kotzenori@riken.jp
c  Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama-cho, Toyonaka-shi, Osaka 560-0043, Japan
,
Misako Taichi
a  Biofunctional Synthetic Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan   Fax: +81(48)4679379   Email: kotzenori@riken.jp
,
Almira Kurbangalieva
d  Biofunctional Chemistry Laboratory, A. Butlerov Institute of Chemistry, Kazan Federal University, 18 Kremlyovskaya Street, Kazan 420008, Russia
,
Koichi Fukase
c  Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama-cho, Toyonaka-shi, Osaka 560-0043, Japan
,
Yoichi Nakao
b  School of Advanced Science and Engineering, Department of Chemistry and Biochemistry, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan
,
Katsunori Tanaka*
a  Biofunctional Synthetic Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan   Fax: +81(48)4679379   Email: kotzenori@riken.jp
d  Biofunctional Chemistry Laboratory, A. Butlerov Institute of Chemistry, Kazan Federal University, 18 Kremlyovskaya Street, Kazan 420008, Russia
› Author Affiliations
Further Information

Publication History

Received: 13 February 2014

Accepted after revision: 05 March 2014

Publication Date:
07 April 2014 (online)

Abstract

Guanylation proceeded efficiently upon treatment of the various amines with cyanamide in the presence of catalytic amounts of scandium(III) triflate under mild conditions. The method did not require the guanylation reagents to be preactivated, and the reaction proceeded efficiently in water. The method, therefore, has practical utility for substrates that dissolve only in aqueous solutions, for example, peptides or pharmacologically important compounds.

Supporting Information

 
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