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

Dmitry Yu Vandyshev; Khidmet S Shikhaliev; Andrey Yu Potapov; Michael Yu Krysin; Fedor I Zubkov; Lyudmila V Sapronova

doi:10.3762/bjoc.13.252

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

Beilstein J Org Chem. 2017 Nov 30:13:2561-2568. doi: 10.3762/bjoc.13.252. eCollection 2017.

Authors

Dmitry Yu Vandyshev¹, Khidmet S Shikhaliev¹, Andrey Yu Potapov¹, Michael Yu Krysin¹, Fedor I Zubkov², Lyudmila V Sapronova²

Affiliations

¹ Faculty of Chemistry, Voronezh State University, Universitetskaya sq., 1, Voronezh 394018, Russian Federation.
² Faculty of Physics and Mathematics and Natural Sciences, RUDN University, Miklukho-Maklaya St., 6, Moscow 117198, Russian Federation.

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.

Keywords: HPLC–HRESIMS; cascade reaction; diaminoimidazoles; imidazo[1,5-b]pyridazines; itaconimides.