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

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.

CRYSTAL STRUCTURE OF (E)-N′-((1H-PYRROL-2-YL)METHYLENE)-4-HYDROXYBENZOHYDRAZIDE

“…Weak interactions, such as hydrogen, halogen, chalcogen, pnicogen, tetrel and picosagen bonds were extensively used in the synthesis, catalysis, crystal engineering, drug delivery, etc. [1][2][3][4][5][6][7][8][9][10][11] . Among those, hydrogen bonding has turned out to be particularly suitable for design of organic and coordination compounds [12][13][14][15][16][17][18][19] .…”

Crystal structure and Hirshfeld surface analysis of dimethyl (3aS,6R,6aS,7S)-2-(2,2,2-trifluoroacetyl)-2,3-dihydro-1H,6H,7H-3a,6:7,9a-diepoxybenzo[de]isoquinoline-3a1,6a-dicarboxylate

“…These weak forces can also control or organize the aggregation, conformation, tertiary and quaternary structure of a molecule, and its stabilization or other particular properties (Legon, 2017;Mahmudov et al, 2017a,b). In comparison with well-established hydrogen and halogen bonds (Cavallo et al, 2016;Mahmoudi et al, 2018;Vandyshev et al, 2017), chalcogen, pnicogen, tetrel and icosagen bonds are much less explored (Mahmudov et al, 2017a;Scheiner, 2013;Mikherdov et al, 2016).…”

Crystal structure and Hirshfeld surface analysis of 3,3′,3′′-[(1,3,5-triazine-2,4,6-triyl)tris(oxy)]tris(5,5-dimethylcyclohex-2-en-1-one)

“…Usually, the active methylene group of -diketones is a reaction centre in the organic transformations of this class of compounds (Ma et al, 2017a,b;Gurbanov et al, 2017aGurbanov et al, ,b, 2018Borisova et al, 2018;Jlassi et al, 2018). In contrast, there are few reports on the reactivity of -diketones as O-nucleophiles (Yusifov et al, 2013;Ledenyova et al, 2018;Vandyshev et al, 2017;Nasirova et al, 2017). Herein we found a C-O coupling reaction between cyanuric chloride and dimedone leading to the title compound 3,3 0 ,3 00 -[(1,3,5-triazine-2,4,6-triyl)tris(oxy)]tris(5,5-dimethylcyclohex-2-en-1-one) ( Fig.…”