Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5224325 | Tetrahedron | 2010 | 6 Pages |
Abstract
A 'one-flask' synthesis of guanidines was developed by reacting isocyanates and isothiocyanates with sodium bis(trimethylsilyl)amide followed by addition of primary or secondary amines with a catalytic amount of AlCl3. The desired guanidines were obtained in good yields and the reaction was applicable to aliphatic and aromatic substrates. A plausible mechanism was proposed through the generation of cyanamide anion from isocyanates or isothiocyanates with sodium bis(trimethylsilyl)amide. Addition of amines and catalytic amount of AlCl3 smoothly converted the cyanamides to the desired guanidines.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Chun-Yen Chen, Hui-Chang Lin, Yu-Ying Huang, Kun-Lung Chen, Jiann-Jyh Huang, Mou-Yung Yeh, Fung Fuh Wong,