4-(1-Allyl-4,5-diphenyl-1H-imidazol-2-yl)-N,N-dimethylaniline

Abstract

The title compound, C26H25N3, crystallizes with four independent mol­ecules, 1–4, in the asymmetric unit of the triclinic unit cell. The allyl substituents on the imidazole rings adopt similar conformations in all four mol­ecules. The imadazole and the 4-and 5-substituted phenyl rings of two pairs of molecules in the asymmetric unit stack parallel to (110). In contrast, the dimethyl­aniline systems in these pairs of mol­ecules are almost normal to one another, with dihedral angles of 85.84 (10) and 85.65 (10)° between the benzene rings of the two dimethyl­aniline fragments of mol­ecules 1 and 2, and 3 and 4, respectively. The crystal structure features an extensive series of C—H⋯π inter­actions that link the mol­ecules into undulating rows along the c axis. The crystal studied was a pseudo-merohedral twin with twin law [-100, 0-10, 111] and the BASF parameter refined to 0.513 (3).

New Method for Synthesis of Multi‐substituted Imidazoles

“…13 C NMR of 8l–s showed five characteristic significant signals around 13.000, 21.000, 28.000, 29.000, and 44.000, which belong to the carbon atoms of pentyl moiety, and the peak of methylene disappeared in DEPT confirming that, in the other hand, the structure of the compounds 8a , 8b , 8d , 8e , 8i , 8l , 8n , 8r , and 8s were confirmed by X‐ray single crystal analysis (Fig. ) .…”

“…Also, compounds 8a–s were prepared by second method via alkylation of 2,4,5‐trisubstituted imidazoles with allyl bromide or pentyl bromide in DMSO/KOH system at 30–60°C. However, alkylation of imidazole method afforded better yields of the product under mild conditions in a shorter reaction time (Scheme ) .…”

“…The molecular structures of 8a , 8b , 8d , 8e , 8i , 8l , 8n , 8r , and 8s showing the atom numbering with ellipsoids drawn at the 50% probability level . [Color figure can be viewed at wileyonlinelibrary.com]…”

2,4,5-Triphenyl-1-(prop-2-en-1-yl)-1H-imidazole

“…For the biological significance of imidazole derivatives, see, for example: Kumar (2010); Castañ o et al (2008); Banfi et al (2006); Bogle et al (1994). For the synthesis and the structures of similar imidazoles, see: Mohamed et al (2013a,b); Akkurt et al (2013). For puckering parameters, see: Cremer & Pople (1975).…”

4-(4,5-Diphenyl-1H-imidazol-2-yl)-N,N-dimethylaniline

“…For background on imidazoles, see: Ucucu et al (2001). For similar structures, see : Yanover & Kaftory (2009); Akkurt et al (2013); Prabhuswamy et al (2013). Table 1 Hydrogen-bond geometry (Å , ).…”