A solution-phase parallel synthesis of alkylated guanidines from thioisocyanates and amines.
Mol Divers
; 17(3): 471-7, 2013 Aug.
Article
em En
| MEDLINE
| ID: mdl-23636682
ABSTRACT
An efficient solution-phase parallel synthesis of alkylated guanidines from commercial thioisocyanates and amines is described. In the first step, a thioisocyanate reacts with one equivalent of ammonia or a primary or secondary amine to give a thiourea intermediate. The latter is S-alkylated with n-dodecyl bromide resulting in the corresponding thiouronium bromide. Finally, the reaction of the thiouronium salt with a second equivalent of ammonia or a primary amine yields an alkylated guanidine. All three synthetic steps are easily combined in a one-pot high-yielding procedure with a simple work-up. Ca. 250 guanidine derivatives with high structural and functional diversity were synthesized by the developed method. 35 representatives reported in this study were fully characterized.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Isocianatos
/
Aminas
/
Guanidinas
Idioma:
En
Ano de publicação:
2013
Tipo de documento:
Article