A novel synthetic approach to hydroimidazo[1,5-b]pyridazines by the recyclization of itaconimides and HPLC-HRMS monitoring of the reaction pathway

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Abstract

The novel cascade two-stage reaction between itaconimides and 1,2-diamino-4-phenylimidazole proceeds regio- and chemoselectively to form tetrahydroimidazo[1,5-b]pyridazines and includes nucleophilic C-addition by the activated C=C double bond and subsequent intramolecular recyclization of the intermediate with the amino group involved.

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Vandyshev, D. Y., Shikhaliev, K. S., Potapov, A. Y., Krysin, M. Y., Zubkov, F. I., & Sapronova, L. V. (2017). A novel synthetic approach to hydroimidazo[1,5-b]pyridazines by the recyclization of itaconimides and HPLC-HRMS monitoring of the reaction pathway. Beilstein Journal of Organic Chemistry, 13, 2561–2568. https://doi.org/10.3762/bjoc.13.252

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