Synthesis, spectroscopic and crystal structure analysis of 2-(4-fluorobenzyl)-6-(4-methoxyphenyl)imidazo[2,1-b][1,3,4]thiadiazole and its morpholinomethyl derivative

Banu, Afshan; Vasundhara, D. E.; Lamani, Ravi S.; Khazi, Imtiyaz Ahmed M.; Begum, Noor Shahina

doi:10.1016/j.jscs.2011.03.010

Cited by 4 publications

(1 citation statement)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…9, namely, 2-cyclohexyl-6-(4-bromophenyl)imidazo [2,1-b][1,3,4]thiadiazole-5-carbaldehyde (Shahina Begum et al, 2008) and 2-(4-fluorobenzyl)-6phenylimidazo [2,1-b][1,3,4]thiadiazole-5-cabaldehyde (Banu et al, 2010a). The reported structures for analogues of the products (I)-(III) carrying heterocyclic substituents at position 5 are few, but they include 5-(morpholin-4-ylmethyl)-2-(phenoxymethyl)-6-phenylimidazo [2,1-b][1,3,4]thiadiazole (Da et al, 2012) and 2-(4-fluorobenzyl)-6-(4-methoxyphenyl)-5-(morpholin-4-ylmethyl)imidazo [2,1-b][1,3,4]thiadiazole (Banu et al, 2013). Finally, we note an isostructural pair of compounds carrying 1,2-benzoxazole substituents at position 2 (Banu, Ziaulla et al, 2011b) and its 6-(4-bromophenyl) analogue (Banu, Ziaulla et al, 2011a).…”

Section: Database Surveymentioning

confidence: 99%

Crystal structures of three 6-aryl-2-(4-chlorobenzyl)-5-[(1H-indol-3-yl)methyl]imidazo[2,1-b][1,3,4]thiadiazoles

et al. 2020

View full text Add to dashboard Cite

Three title compounds, namely, 2-(4-chlorobenzyl)-5-[(1H-indol-3-yl)methyl]-6-phenylimidazo[2,1-b][1,3,4]thiadiazole, C26H19ClN4S, (I), 2-(4-chlorobenzyl)-6-(4-fluorophenyl)-5-[(1H-indol-3-yl)methyl]imidazo[2,1-b][1,3,4]thiadiazole, C26H18ClFN4S, (II), and 6-(4-bromophenyl)-2-(4-chlorobenzyl)-5-[(1H-indol-3-yl)methyl]imidazo[2,1-b][1,3,4]thiadiazole, C26H18BrClN4S, (III), have been prepared using a reductive condensation of indole with the corresponding 6-aryl-2-(4-chlorobenzyl)imidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehydes (aryl = phenyl, 4-fluorophenyl or 4-bromophenyl), and their crystal structures have been determined. The asymmetric unit of compound (I) consists of two independent molecules and one of the molecules exhibits disorder of the 4-chlorobenzyl substituent with occupancies 0.6289 (17) and 0.3711 (17). Each type of molecule forms a C(8) chain motif built from N—H...N hydrogen bonds, which for the fully ordered molecule is reinforced by C—H...π interactions. In compound (II), the chlorobenzyl unit is again disordered, with occupancies 0.822 (6) and 0.178 (6), and the molecules form C(8) chains similar to those in (I), reinforced by C—H...π interactions involving only the major disorder component. The chlorobenzyl unit in compound (III) is also disordered with occupancies of 0.839 (5) and 0.161 (5). The molecules are linked by a combination of one N—H...N hydrogen bond and four C—H...π interactions, forming a three-dimensional framework.

show abstract