A new synthesis of 2,3-di- or 2,3,3-trisubstituted 2,3-dihydro-4-pyridones by reaction of 3-ethoxycyclobutanones and N-p-toluenesulfonyl imines using titanium(IV) chloride: synthesis of (+/-)-bremazocine

Jun-ichi Matsuo; Ryohei Okado; Hiroyuki Ishibashi

doi:10.1021/ol1012313

A new synthesis of 2,3-di- or 2,3,3-trisubstituted 2,3-dihydro-4-pyridones by reaction of 3-ethoxycyclobutanones and N-p-toluenesulfonyl imines using titanium(IV) chloride: synthesis of (+/-)-bremazocine

Org Lett. 2010 Jul 16;12(14):3266-8. doi: 10.1021/ol1012313.

Authors

Jun-ichi Matsuo¹, Ryohei Okado, Hiroyuki Ishibashi

Affiliation

¹ School of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan. jimatsuo@p.kanazawa-u.ac.jp

PMID: 20568828
DOI: 10.1021/ol1012313

Abstract

N-p-Toluenesulfonyl (Ts) aldimines reacted with 3-ethoxycyclobutanones by catalysis of titanium(IV) chloride to afford 2,3-di- or 2,3,3-trisubstituted N-Ts-2,3-dihydro-4-pyridones. Synthesis of (+/-)-bremazocine was efficiently accomplished by using this method.

Publication types

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

MeSH terms

Benzomorphans / chemical synthesis*
Benzomorphans / chemistry*
Catalysis
Cyclobutanes / chemistry*
Imines / chemistry*
Pyridones / chemical synthesis*
Pyridones / chemistry*
Stereoisomerism
Titanium / chemistry*

Substances

Benzomorphans
Cyclobutanes
Imines
Pyridones
Titanium
titanium trichloride
bremazocine