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53. Regioselective Azidation of 2,4-Dichloroquinolines (Organic azides in heterocyclic synthesis, 18)
Steinschifter W., Stadlbauer W., J. Prakt. Chem. 336 (1994) 311-318

Abstract: Reactions of 2,4-dichloroquinolines with sodium azide in DMF lead either regioselectively to 4-azido-2-chloroquinolines or with excess of sodium azide and catalysts to 5-azido-tetrazolo[1,5-a]quinolines. 2,4-Dichloroquinolines having electron donating substituents in 3-position react with sodium azide in DMF to a mixture of 4-azido-2-chloroquinolines and 5-chloro-tetrazolo[1,5-a]quinolines. When the reaction of the 2,4-dichloroquinolines with sodium azide is carried out in ethanol with addition of methanesulfonic acid, regioselectively 5-chloro-tetrazolo[1,5-a]quinolines are obtained. Structural assignments have been carried out by 13C-NMR spectra, IR spectra and degra- dation reactions of the azido- and tetrazolo group to aminoquinolines) via iminophos- phoranes. It could be shown that in 2-azido/tetrazolo-quinolines the tetra- zole ring structure is the dominant species.


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