Facile Guanidine Formation under Mild Acidic Conditions

An efficient method for converting isothioureas into guanidines was developed. The use of amine salts of bis(trifluoromethanesulfonyl)imide as a nitrogen source was found to induce an efficient conversion under weak acidic conditions at 50 degrees C. The conversion was applicable to the various amin...

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Bibliographic Details
Published inSynlett Vol. 27; no. 18; pp. 2591 - 2596
Main Authors Takeuchi, Kohei, Nakayama, Atsushi, Tanino, Keiji, Namba, Kosuke
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.08.2016
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CONVENIENT SYNTHESIS
CHIRAL BICYCLIC GUANIDINE
cyclic guanidine
REAGENTS
ONE-POT SYNTHESIS
SUBSTITUTED GUANIDINES
PROTECTED GUANIDINES
EFFICIENT GUANYLATION
bis(trifluoromethansulfonyl)imide
ammonium bis(trifluoromethansulfonyl)imidate
LIGHT-SENSITIVE GLYCOSIDES
AMINO-GROUPS
guanidinylation
DERIVATIVES
isothiourea
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Summary:An efficient method for converting isothioureas into guanidines was developed. The use of amine salts of bis(trifluoromethanesulfonyl)imide as a nitrogen source was found to induce an efficient conversion under weak acidic conditions at 50 degrees C. The conversion was applicable to the various amines and carbamate-protected thioureas, and various carbamate-protected cyclic guanidines were obtained in high yields. In particular, ammonium bis(trifluoromethanesulfonyl)imide salt is a useful N1 source with which to construct monoprotected cyclic guanidines.
Bibliography:KAKEN
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0035-1562478