Development of more potent 4-dimethylaminopyridine analogues.
[reaction: see text] The syntheses of bicyclic diaminopyridines 3 and 4 and tricyclic triaminopyridines 5 and 6, two novel series of nucleophilic catalysts, are described. Arguments are made for predicting the superiority of these catalysts over DMAP and even 2, the best esterification catalyst reported to date. The efficiencies of DMAP, PPY, and 2-6 in catalyzing the esterification of tertiary alcohols were compared. As predicted, 5 and 6 were about 6-fold more effective than DMAP and slightly better than 2.
Singh
Satwinder
S
Department of Chemistry, The University of Texas at San Antonio, 6900 North Loop 1604 West, San Antonio, Texas 78249, USA.
Das
Goutam
G
Singh
Om V
OV
Han
Hyunsoo
H
D015761:4-Aminopyridine / Q000031:analogs & derivatives* / Q000032:analysis / Q000138:chemical synthesis; D000438:Alcohols / Q000737:chemistry; D002384:Catalysis; D004952:Esters / Q000737:chemistry; D007700:Kinetics; D008024:Ligands; D008956:Models, Chemical; D026902:Potassium Channel Blockers / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000438:Alcohols; D004952:Esters; D008024:Ligands; D026902:Potassium Channel Blockers; D015761:4-Aminopyridine; C003885:4-dimethylaminopyridine