Synthesis of tetrazole-derived organocatalysts via azido-Ugi reaction with cyclic ketimines.
A new route to tetrazole-derived cyclic amines based on the TMSN3-modified Ugi reaction with 2-substituted cyclic imines was elaborated. The reaction allows the direct preparation of five-, six-, and seven-membered cyclic amines substituted with a tetrazole ring, which are important types of organocatalysts. The scope and limitations of this method are discussed. In the case of the Ugi reaction with benzyl isocyanide, the N-substituted tetrazoles can be easily debenzylated under catalytic hydrogenation conditions to form NH-tetrazoles in quantitative yields. It was demonstrated that both enantiomers of tetrazole-derived cyclic amines can be prepared by resolution with tartaric acid, thereby initiating a simple route to chiral derivatives. One of the obtained chiral tetrazoles was efficiently used as an organocatalyst in the amination reaction.
Department of Chemistry, Moscow State University , Leninskie Gory, Moscow 119992, Russia.
Olga I
OI
Shmatova
Valentine G
VG
Nenajdenko
D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D013777:Tetrazoles / Q000737:chemistry*
D000588:Amines; D001386:Azides; D007097:Imines; D009570:Nitriles; D013777:Tetrazoles; C542835:ketimine; C045574:1H-tetrazole