Picture map of Europe with pins indicating European capital cities

Open Access research with a European policy impact...

The Strathprints institutional repository is a digital archive of University of Strathclyde's Open Access research outputs. Strathprints provides access to thousands of Open Access research papers by Strathclyde researchers, including by researchers from the European Policies Research Centre (EPRC).

EPRC is a leading institute in Europe for comparative research on public policy, with a particular focus on regional development policies. Spanning 30 European countries, EPRC research programmes have a strong emphasis on applied research and knowledge exchange, including the provision of policy advice to EU institutions and national and sub-national government authorities throughout Europe.

Explore research outputs by the European Policies Research Centre...

Unexpected Dealkylation During Nucleophilic Substitution: Synthesis of 2-N,N-Dialkylamino Benzoxazoles and Benzothiazoles

Khalaf, A.I. and Alvarez, R.G. and Suckling, C.J. and Waigh, R.D. (2000) Unexpected Dealkylation During Nucleophilic Substitution: Synthesis of 2-N,N-Dialkylamino Benzoxazoles and Benzothiazoles. Tetrahedron, 56 (43). pp. 8567-8571. ISSN 0040-4020

Full text not available in this repository. Request a copy from the Strathclyde author

Abstract

Mild reaction conditions are described for the preparation of a number of 2-alkyl- and 2-arylaminobenzoxazoles and benzothiazoles from 2-chlorobenzoxazole and 2-chlorobenzothiazole and N-methyl or other simple N-alkyl tertiary amines. The reaction proceeds neat or in THF solution and involves dealkylation of the amine reactant by nucleophilic substitution by chloride. In the case of N-methylpyrrolidine and N-methylpiperidine demethylation was not observed and the major product was formed by ring opening to give chlorobutyl- and chloropentyl-methylamino substituted benzoxazoles and benzothiazoles. Treatment of the chlorobutyl derivative with iodide in acetone afforded the new 1H,2H,3H,4H,5H-[1,3]diazepino[2,1-b][1,3]benzoxazol-6-ium ring system.