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.
Original language | English |
---|---|
Pages (from-to) | 1892-1897 |
Number of pages | 6 |
Journal | Tetrahedron |
Volume | 66 |
Issue number | 10 |
DOIs | |
Publication status | Published - 2010 Mar 6 |
Externally published | Yes |
All Science Journal Classification (ASJC) codes
- Biochemistry
- Drug Discovery
- Organic Chemistry