Journal fur Praktische Chemie - Chemiker-Zeitung p. 311 - 318 (1994)
Update date:2022-08-03
Topics:
Steinschifter, Waltraud
Stadlbauer, Wolfgang
Reactions of 2,4-dichloroquinolines (2a-f) with sodium azide in DMF lead either regioselectively to 4-azido-2-chloroquinolines (3a-f) or with excess of sodium azide and catalysts to 5-azido-tetrazolo<1,5-a>quinolines (4a-f). 2,4-Dichloroquinolines (2g-i) having electron donating substituents in 3-position react with sodium azide in DMF to a mixture of 4-azido-2-chloroquinolines (3g-i) and 5-chlorotetrazolo<1,5-a>quinolines (5g-i).When the reaction of the 2,4-dichloroquinolines (2a-i) with sodium azide is carried out in ethanol with addition of methanesulfonic acid, regioselectively 5-chloro-tetrazolo<1,5-a>quinolines (5a-i) are obtained.Structural assignments of 3 and 5 have been carried out by 13C-NMR spectra, IR spectra and degradation reactions of the azido- and tetrazolo group to aminoquinolines (7 and 10) via iminophosphoranes (8 and 9).It could be shown that in 2-azido/tetrazolo-quinolines (4 and 5) the tetrazole ring structure is the dominant species.
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