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

Autor: Vandyshev DY; Faculty of Chemistry, Voronezh State University, Universitetskaya sq., 1, Voronezh 394018, Russian Federation., Shikhaliev KS; Faculty of Chemistry, Voronezh State University, Universitetskaya sq., 1, Voronezh 394018, Russian Federation., Potapov AY; Faculty of Chemistry, Voronezh State University, Universitetskaya sq., 1, Voronezh 394018, Russian Federation., Krysin MY; Faculty of Chemistry, Voronezh State University, Universitetskaya sq., 1, Voronezh 394018, Russian Federation., Zubkov FI; Faculty of Physics and Mathematics and Natural Sciences, RUDN University, Miklukho-Maklaya St., 6, Moscow 117198, Russian Federation., Sapronova LV; Faculty of Physics and Mathematics and Natural Sciences, RUDN University, Miklukho-Maklaya St., 6, Moscow 117198, Russian Federation.
Jazyk: angličtina
Zdroj: Beilstein journal of organic chemistry [Beilstein J Org Chem] 2017 Nov 30; Vol. 13, pp. 2561-2568. Date of Electronic Publication: 2017 Nov 30 (Print Publication: 2017).
DOI: 10.3762/bjoc.13.252
Abstrakt: 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.
Databáze: MEDLINE