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.
Original language | English |
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Pages (from-to) | 8567-8571 |
Number of pages | 4 |
Journal | Tetrahedron |
Volume | 56 |
Issue number | 43 |
DOIs | |
Publication status | Published - 20 Oct 2000 |
Keywords
- 2-arylaminobenzoxazoles
- 2-chlorobenzoxazole
- 2-chlorobenzothiazole
- dealkylation
- [1
- 3]diazepino[2
- 1-b][1
- 3]benzazoles