Abstract
Language | English |
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Pages | 8567-8571 |
Number of pages | 4 |
Journal | Tetrahedron |
Volume | 56 |
Issue number | 43 |
DOIs | |
Publication status | Published - 20 Oct 2000 |
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Keywords
- 2-arylaminobenzoxazoles
- 2-chlorobenzoxazole
- 2-chlorobenzothiazole
- dealkylation
- [1
- 3]diazepino[2
- 1-b][1
- 3]benzazoles
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Unexpected Dealkylation During Nucleophilic Substitution: Synthesis of 2-N,N-Dialkylamino Benzoxazoles and Benzothiazoles. / Khalaf, A.I.; Alvarez, R.G.; Suckling, C.J.; Waigh, R.D.
In: Tetrahedron, Vol. 56, No. 43, 20.10.2000, p. 8567-8571.Research output: Contribution to journal › Article
TY - JOUR
T1 - Unexpected Dealkylation During Nucleophilic Substitution: Synthesis of 2-N,N-Dialkylamino Benzoxazoles and Benzothiazoles
AU - Khalaf, A.I.
AU - Alvarez, R.G.
AU - Suckling, C.J.
AU - Waigh, R.D.
PY - 2000/10/20
Y1 - 2000/10/20
N2 - 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.
AB - 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.
KW - 2-arylaminobenzoxazoles
KW - 2-chlorobenzoxazole
KW - 2-chlorobenzothiazole
KW - dealkylation
KW - [1
KW - 3]diazepino[2
KW - 1-b][1
KW - 3]benzazoles
UR - http://dx.doi.org/10.1016/S0040-4020(00)00802-4
U2 - 10.1016/S0040-4020(00)00802-4
DO - 10.1016/S0040-4020(00)00802-4
M3 - Article
VL - 56
SP - 8567
EP - 8571
JO - Tetrahedron
T2 - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 43
ER -