Beilstein J. Org. Chem.2017,13, 2561–2568, doi:10.3762/bjoc.13.252
-addition by the activated C=C double bond and subsequent intramolecular recyclization of the intermediate with the amino group involved.
Keywords: cascade reaction; diaminoimidazoles; HPLC–HRESIMS; imidazo[1,5-b]pyridazines; itaconimides; Introduction
Among the numerous bicyclic fused imidazole
the HPLC–HRESIMS monitoring of the reaction confirm its selectivity.
Conclusion
In summary, a new regioselective and chemoselective cascade reaction of N-arylitaconimides with 1,2-diamino-4-phenylimidazole as 1,3-C,N-dinucleophile was developed to synthesize tetrahydroimidazo[1,5-b]pyridazines. The
of the interaction of itaconimides 1 with diaminoimidazole 4.
1H,13C-HMBC correlations: the most significant correlations for imidazopyridazine 9d and possible for imidazodiazepine 10d.
Yields of the interaction products 9 of N-arylitaconimides 1a–g and diaminoimidazole 4.
Results of HPLC–HRESIMS
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Graphical Abstract
Scheme 1:
Intramolecular cyclization of 3-(aminomethyl)pyridazines and related compounds (route A). Condition...