A novel solid-phase synthesis of highly diverse guanidines: reactions of primary amines attached to the T2 linker.
The reaction of primary amines with the T2 diazonium resin generates polymer-bound triazenes, which can in turn be acylated by the addition of isothiocyanate. The formed thioureas are readily transformed into the corresponding guanidines by the reaction with amines in the presence of mercury(II) oxide, tosyl chloride, or silver nitrate. This reaction sequence furnishes trisubstituted guanidines that are potentially useful pharmacophores.
Dahmen
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Institut für Organische Chemie der Technischen Hochschule Aachen, Professor-Pirlet-Strasse 1, D-52074 Aachen, Germany.
Bräse
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D000588:Amines / Q000737:chemistry*; D003979:Diazonium Compounds / Q000737:chemistry; D006146:Guanidines / Q000138:chemical synthesis*; D012117:Resins, Synthetic / Q000737:chemistry; D014226:Triazenes / Q000138:chemical synthesis / Q000737:chemistry
D000588:Amines; D003979:Diazonium Compounds; D006146:Guanidines; D012117:Resins, Synthetic; D014226:Triazenes