5-(2-Methylfuran-3-yl)-N-phenyl-1,3,4-oxadiazol-2-amine

Abstract

In the title compound, C13H11N3O2, the furan ring is disordered over two orientations, with occupancies of 0.902 (2) and 0.098 (2). The dihedral angles between the central oxadiazole ring and the pendant phenyl ring and the furan ring (major disorder component) are 10.12 (11) and 1.76 (15)°, respectively. A short intramolecular C—H...O contact generates anS(6) ring. In the crystal, inversion dimers linked by pairs of N—H...N hydrogen bonds generateR22(8) loops. The dimers are linked by C—H...π and π–π interactions [range of centroid–centroid distances = 3.301 (7)–3.689 (1) Å], generating a three-dimensional network.

CoII-catalysed synthesis of N-(4-methoxyphenyl)-5-(pyridin-4-yl)-1,3,4-oxadiazol-2-amine hemihydrochloride monohydrate

“…The C3-C7/N4 pyridyl, C1/C2/N2/N3/O1 oxadiazole and C8-C13 phenyl rings are close to co-planar with the dihedral angles between pyridyl and oxadiazole rings being 4.88 (9) � , oxadiazole and phenyl rings 4.27 (10) � and pyridyl and phenyl rings 2.27 (9) � . The bond distances and angles of the 1,3,4-oxadiazole ring [C1-N2 = 1.298 (2); C2-N3 = 1.277 (2) A ˚] are in good agreement with values reported previously (Jasinski et al, 2011;Paswan et al, 2015Paswan et al, , 2016Singh et al, 2007). The C-N bond distance in the pyridine ring, C5-N4 = 1.336 (2) A ˚, is slightly longer than the corresponding bond in a similar compound (1.326 (2) A ˚; Singh et al, 2006), probably due to the N� � �H interaction (Fig.…”

“…We have previously reported the cyclo-desulfurization of several N-acylhydrazine carbodithioates into the corresponding 1,3,4-oxadiazole in the presence of manganese(II) acetate via the loss of H 2 S where the Mn II ion presumably behaves as a weak Lewis acid (Paswan et al, 2015(Paswan et al, , 2016Gond et al, 2022). In the present work, a similar reaction is reported in presence of Co II chloride.…”