4-Aminopyridine catalyzed direct and regioselective acylation of N-tosylhydrazide

Kosuke Namba; Isamu Shoji; Mugio Nishizawa; Keiji Tanino

doi:10.1021/ol9021194

4-Aminopyridine catalyzed direct and regioselective acylation of N-tosylhydrazide

Org Lett. 2009 Nov 5;11(21):4970-3. doi: 10.1021/ol9021194.

Authors

Kosuke Namba¹, Isamu Shoji, Mugio Nishizawa, Keiji Tanino

Affiliation

¹ Division of Chemistry, Graduate School of Science, Hokkaido University, Kita-ku, Sapporo 060-0810, Japan. namba@mail.sci.hokudai.ac.jp

PMID: 19795873
DOI: 10.1021/ol9021194

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

4-Aminopyridine / chemistry*
Acylation
Catalysis
Hydrazines / chemistry*
Molecular Structure
Stereoisomerism
Tosyl Compounds / chemistry*

Substances

Hydrazines
Tosyl Compounds
4-Aminopyridine