Oxidation of Lactams to Cyclic Imides

Solvent-free synthesis and in-silico molecular docking study of (E)-3-(β-C-glycosylmethylidene)-N-aryl/alkyl succinimides

“…24 The debenzylation of (E)-3-(2,3,4,6-tetra-O-benzyl-C-glucosylmethylidene)-Nphenyl succinimide (3a) with 10% Pd/C under H 2 (g) atmosphere in methanol at 25 °C accompanied by the reduction of the methylidene double bond to the methylene group at the C-3 position of the succinimide ring afforded an inseparable diastereomeric mixture of compound 5a. 25 The structures of the known compounds C-glycopyranosyl aldehydes 1a-c were confirmed based on 1 H and 13 C NMR spectra, and the obtained data are consistent with the literature. 23 The structures of all synthesized novel compounds, i.e., 3a-m, 4a-m and 5a, were unambiguously established on the basis of their IR, 1 H, and 13 C NMR spectra, and HRMS data analysis.…”

“…25 The structures of the known compounds C-glycopyranosyl aldehydes 1a-c were confirmed based on 1 H and 13 C NMR spectra, and the obtained data are consistent with the literature. 23 The structures of all synthesized novel compounds, i.e., 3a-m, 4a-m and 5a, were unambiguously established on the basis of their IR, 1 H, and 13 C NMR spectra, and HRMS data analysis. Furthermore, compound 4k was confirmed by analyzing its single crystal structure data (Fig.…”

“…The IR spectra were recorded on a PerkinElmer model 2000 FTIR spectrometer by making a KBr disk for solid samples. 1 H and 13 C NMR spectra were recorded on Jeol Delta 400 and 100.6 MHz spectrometers, respectively, using tetramethylsilane (TMS) as an internal standard. The chemical shift values are on a δ scale and the coupling constant values ( J) are in Hz.…”

“…(E)-3-(2,3,4,6-Tetra-O-benzyl-C-glucosylmethylidene)-N-phenyl succinimide (3a). It was obtained as a pale yellow gel (580 mg) in 90% yield; IR (KBr, cm −1 ): 3030, 2922, 1770, 1705, 1665, 1626, 1607, 1297, 1098, 734, 697; [α] 27 D = −67.0 (c 0.3, chloroform); 1 H NMR (400 MHz, CDCl 3 ): δ 3.42-3.51 (m, 4H), 3.62-3.69 (m, 3H), 3.76 (t, 1H, J = 8.9 Hz), 4.04 (dd, 1H, J = 6.3 and 9.7 Hz), 4.52-4.59 (m, 4H), 4.86 (t, 2H, J = 11.0 Hz), 4.95 (s, 2H), 6.94 (d, 1H, J = 6.2 Hz), 7.18 (dd, 2H, J = 2.3 and 6.8 Hz), 7.22-7.24 (m, 2H), 7.28-7.35 (m, 18H), 7.41 (d, 1H, J = 7.3 Hz), 7.50 (t, 2H, J = 7.6 Hz); 13 C NMR (100.6 MHz, CDCl 3 ): δ 33. 4, 68.9, 73.7, 75.2, 75.8, 75.9, 77.4, 78.0, 79.0, 82.1, 87.0, 126.4, 127.9, 128.0, 128.3, 128.6, 128.7, 128.8, 129.2, 132.0, 134.0, 137.5, 137.9, 138.0, 138.4, 168.8, 173.3 (E)-3-(2,3,4,6-Tetra-O-benzyl-C-glucosylmethylidene)-N-(4-bromophenyl) succinimide (3b).…”

“…1. 13 Andrimid isolated from Nilaparvata lugens is active against pathogens of rice plants 14 and cladosporitin B isolated from the mangrove-derived fungus Cladosporium sp. HNWSW-1 showed cytotoxicity against many cancerous cell lines.…”