Crystal structure and Hirshfeld surface analysis of two imidazo[1,2-a]pyridine derivatives: N-tert-butyl-2-(4-methoxyphenyl)-5-methylimidazo[1,2-a]pyridin-3-amine and N-tert-butyl-2-[4-(dimethylamino)phenyl]imidazo[1,2-a]pyridin-3-amine

Abstract

In the title imidazo[1,2-a]pyridine derivatives, N-tert-butyl-2-(4-meth­oxy­phen­yl)-5-methyl­imidazo[1,2-a]pyridin-3-amine, (I), and N-tert-butyl-2-[4-(di­methyl­amino)­phen­yl]imidazo[1,2-a]pyridin-3-amine, (II), the 4-meth­oxy­phenyl ring in (I) and the 4-(di­methyl­amino)­phenyl ring in (II) are inclined to the mean planes of the respective imidazole rings by 26.69 (9) and 31.35 (10)°.

Crystal structure, DFT calculation, Hirshfeld surface analysis and energy framework study of 6-bromo-2-(4-bromophenyl)imidazo[1,2-a]pyridine

“…The N1 C9 bond is slightly longer than similar bonds of reported imidazo[1,2-a] pyridine structures (see x7 for a listing of these structures), which may be attributed to the presence of the intramolecular bond (H5Á Á ÁN1). Overall, the bond lengths and angles of the phenyl ring and the imidazo[1,2-a]pyridine ring system are in normal ranges and compare well with those of other imidazo[1,2-a]pyridine derivatives (Zhang et al, 2005;Dhanalakshmi et al, 2018).…”

N-(tert-Butyl)-2-(2-nitrophenyl)imidazo[1,2-a]pyridin-3-amine

“…N-(tert-Butyl)-2-(2-nitrophenyl)imidazo[1,2-a]pyridin-3amine was prepared by our reported method (reagent quantities: 1 eq. of tert-butyl isocyanide and 0.5 mmol of iodine; Dhanalakshmi et al, 2018) and confirmed by NMR, ESI-MS and IR spectroscopy. 1 H NMR (400 MHz, CDCl 3 ) = 8.19 (d, J = 6.9, 1H), 7.91 (dd, J = 8.1, 0.9, 1H), 7.80 (d, J = 1.2, 1H), 7.65 (d, J = 1.1, 1H), 7.51 (dd, J = 16.4, 4.9, 2H), 7.16 (ddd, J = 9.0, 6.7, 1.2, 1H), 6.81 (d, J = 0.9, 1H), 0.95 (s, 9H).…”

“…These compounds are highly active against human cytomegalovirus and varicella-zoster virus (Gueiffier et al,1998). In a continuation of our studies on imdiazole derivatives (Dhanalakshmi et al, 2018;Mala et al, 2019), we herein report the synthesis and crystal structure analysis of the title compound.…”