Maud Hervet, C. Galtier, C. Enguehard
Jul 1, 2002
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0
Influential Citations
2
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Journal
Journal of Heterocyclic Chemistry
Abstract
The synthesis of 2-substitutedimidazo[1,2-b]pyridazines and their reactivity towards electrophilic substitutions are reported. The nitration was shown to be very dependent on the nature of the 2 substituent. Nitrosation using sodium nitrite in acetic acid media as a general method failed in all cases whereas chlorination was observed in warm hydrochloric acid. In order to ascertain the structure of some chloro derivatives, chlorination using N-chlorosuccinimide was also reported. Depending of the nature of the substituent, the reaction occurred at the C-3 imidazolic position and/or at the substituent on position 2. The 3-nitroso-2-phenyl derivative was finally obtained using an alternative synthetic pathway by direct condensation of 3-amino-6-chloropyridazine to ω-chloro-ω-nitrosoacetophenone. The structural determinations were ascertained using high field lH and 13C-NMR.