4-Aminopyridine catalyzed direct and regioselective acylation of N-tosylhydrazide.
An efficient and simple method for selective acylation of either one of two nitrogen atoms of tosylhydrazide was developed. The selectivity was drastically controlled by a catalytic amount of 4-aminopyridine or 4-(dimethylamino)pyridine with common acylating agents. The nitrogen atom masked with a tosyl group was acylated in the presence of 4-aminopyridine, whereas the primary nitrogen atom was acylated in the absence of 4-aminopyridine.
Namba
Kosuke
K
Division of Chemistry, Graduate School of Science, Hokkaido University, Kita-ku, Sapporo 060-0810, Japan. namba@mail.sci.hokudai.ac.jp
Shoji
Isamu
I
Nishizawa
Mugio
M
Tanino
Keiji
K
D015761:4-Aminopyridine / Q000737:chemistry*; D000215:Acylation; D002384:Catalysis; D006834:Hydrazines / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D014105:Tosyl Compounds / Q000737:chemistry*
D006834:Hydrazines; D014105:Tosyl Compounds; D015761:4-Aminopyridine