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2008, The Journal of Organic Chemistry
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34 pages
1 file
All the reagents were obtained from commercial sources (Sigma-Aldrich) and were used without further purification. 1 H and 13 C-NMR spectra were acquired on a Varian Mercury Plus 400 MHz and on a Varian Unit Inova 700 MHz in CD 3 OD or CDCl 3 . Chemical shifts are reported in parts per million (δ) relative to the residual solvent signals: CD 2 HOD 3.31 and CHCl 3 7.27 for 1 H-NMR; CD 2 HOD 49.0 and CHCl 3 77.0 for 13 C-NMR. 1 H-NMR chemical shifts were assigned by 2D NMR experiments. The abbreviations s, bs, d, dd and m stand for singlet, broad singlet, doublet, doublet of doublets and multiplet, respectively. HPLC analyses and purifications were carried out on a Jasco UP-2075 Plus pump equipped with a Jasco UV-2075 Plus UV detector using a 4.60 x 150 mm LUNA (Phenomenex) silica column (particle size 5 µm) eluted with a linear gradient of MeOH in AcOEt (from 0 to 5% in 15 min, flow 1.0 mL min -1 , system A), with a linear gradient of AcOEt in n-hexane (from 0 to 100% in 30 min, flow 1.0 mL min -1 , system B) or using a 4.8 x 150 mm C-18 reverse-phase column (particle size 5 µm) eluted with a linear gradient of MeOH in H 2 O (from 0 to 100% in 30 min, flow 1.3 mL min -1 , system C). UV spectra were recorded on a Jasco V-530 UV spectrophotometer. High Resolution MS spectra were recorded on a Bruker APEX II FT-ICR mass spectrometer using electrospray ionization (ESI) technique in positive mode. Elemental analyses were performed on a Thermo Finnigan Flash EA 1112 CHN analyser. IR spectra were recorded on a Jasco FT-IR 430 spectrophotometer. Optical rotations were determined on a Jasco polarimeter using a 1 dm cell at 25 °C; concentrations are in g/100 mL. Preparative PLC chromatography was performed using F254 silica gel plates (0.5 mm thick, Merck). Analytical TLC analyses were performed using F254 silica gel plates (0.2 mm thick, Merck). TLC spots were detected under UV light (254 nm). For MTS assays the UV absorbance at 490 nm was read using a Beckman Anthos 96 well Microplate Reader.
Journal of the Serbian Chemical Society , 2017
A series of novel bis(1,2,3-triazoles) derivatives 7a–m were synthesized by the 1,3-dipolar cycloaddition (click-reaction) of 1-methyl-3,5-bis(2-(prop-2-yn-1-yloxy)phenyl)-4,5-dihydro-1H-pyrazole (5) with various aralkyl azides 6a–m in the presence of sodium ascorbate and copper sulphate with good yields. The required precursor 5 was synthesized by reacting (E)-1,3-bis(2-hydroxyphenyl)prop-2-en-1-one (3) with methylhydrazine hydrate via 2,2′-(1-methyl-4,5-dihydro-1H-pyrazole-3,5-diyl)diphenol 4, followed by reaction with propargyl bromide. The homogeneity of all the newly synthesized compounds was checked by TLC. The IR, NMR, mass spectral data and elemental analysis were in accord with the assigned structure. The title compounds were evaluated for their antibacterial activity against various bacterial strains, i.e., Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Bacillus subtilis; compounds 7f–7h and 7j were found to be moderately active against the bacteria, when compared with that of the standard drug. Furthermore, the same library of compounds was evaluated for their antioxidant activity using the nitric oxide radical scavenging activity. The results of the study showed that compounds 7e–7h and 7k–7m showed good radical scavenging activity.
Partly hydrogenated 2-[5-methyl(bromo, nitro)furan-2-yl]-substituted furo [3,2-c]quinolines, pyrano-[3,2-c]quinolines, and 4-ethoxyquinolines were synthesized by the imino Diels-Alder (Povarov) reaction. Cycloadditions of these compounds with maleic, citraconic, and dibromomaleic anhydrides, as well as with acryloyl, methacryloyl, and cinnamoyl chlorides led to the formation of substituted epoxyisoindolo[2,1-a]quinolines and -quinolinecarboxylic acids. Oxidation of the double C=C bond in the adducts, esterification of the carboxy group, and aromatization of the 7-oxabicycloheptene fragment were accomplished. s (3H, COMe), 2.97 d.d.q (1H, 3a-H, J 3a, 4 = 3.2, J 3a, 9b = 7.6, J 3a, 3 = 8.2 Hz), 3.74 d.t -H, 2 J = 3 J = 8.6 Hz), 3.82 q (1H, 2-H, 2 J = 8.4, 3 J = 4.4 Hz), 4.44 br.s (NH), 4.81 d (1H, 4-H, J 3a, 4 = 3.2 Hz), 5.22 d (1H, 9b-H, J 3a, 9b = 7.6 Hz), 6.30 d.d (1H, 3′-H, 4 J = 0.8, 3 J = 3.2 Hz), 6.38 d.d (1H, 4′-H, J 5′, 4′ = 1.8, J 4′, 3′ = 3.2 Hz), 6.59 d (1H, 6-H, J 6, 7 = 8.5 Hz), 7.40 d.d (1H, 5′-H, J 5′, 4′ = 1.8, J 5′, 3′ = 0.8 Hz), 7.74 d.d (1H, 7-H, J 7, 9 = 2.0, J 6, 7 = 8.5 Hz), 7.97 d (1H, 9-H, J 7, 9 = 2.0 Hz). Mass spectrum, m/z (I rel , %): 283 (100) [M] + , 268 (22), 254 (13), 238 (90), 210 (9), 198 (6), 172 (15), 167 (5), 103 (5), 81 (6), 43 (7). Found, %: C 72.31; H 6.21; N 4.78. C 17 H 17 NO 3 . Calculated, %: C 72.07; H 6.05; N 4.94. M 283.12. 1-H), 2.05 m (1H, 1-H), 2.34 d.d.d (1H, exo-10-H, J 9a, exo-10 = 3.9, J exo-10, 11 = 4.8, 2 J = 12.1 Hz), 2.76 d.d (1H, 9a-H, J 9a, exo-10 = 3.9, J 9a, endo-10 = 9.2 Hz), 3.21 m (1H, 13c-H), 3.89-4.03 m (2H, 2-H), 4.47 d (1H, 13b-H, J 13b, 13c = 3.4 Hz), 5.17 d.d (1H, 11-H, J exo-10, 11 = 4.8, J 11, 12 = 1.5 Hz), 5.37 d (1H, 3a-H, J 3a, 13c = 8.2 Hz), 6.47 d.d (1H, 12-H, J 11, 12 = 1.5, J 12, 13 = 5.8 Hz), 6.57 d (1H, 13-H, J 12, 13 = 5.8 Hz), 6.98 d.d (1H, 6-H, J 5, 6 = 7.7, J 4, 6 = 1.5 Hz), 7.21 t (1H, 5-H, J 4, 5 = J 5, 6 = 7.7 Hz), 7.22 d.d (1H, 4-H, J 4, 5 = 7.7, J 4, 6 = 1.5 Hz), 9.45 s (OH); cis isomer: 1.77 d.d (1H, endo-10-H, J 9a, endo-10 = 9.2, 2 J = 11.6 Hz), 1.90 m (1H, 1-H), 2.13 m (1H, 1-H), 2.17 d.d.d (1H, exo-10-H, J 9a, exo-10 = 3.9, J exo-10, 11 = 4.4, 2 J = 11.6 Hz), 2.55 d.d (1H, 9a-H, J 9a, exo-10 = 3.9, J 9a, endo-10 = 9.2 Hz), 3.15 m (1H, 13c-H), 3.89-4.03 m (2H, 2-H), 4.52 d (1H, 13b-H, J 13b, 13c = 2.9 Hz), 5.14 d.d (1H, 11-H, J exo-10, 11 = 4.4, J 11, 12 = 1.5 Hz), 5.35 d (1H, 3a-H, J 3a,13c = 8.2 Hz), 6.53 d.d (1H, 12-H, J 11, 12 = 1.5, J 12, 13 = 5.8 Hz), 6.58 d (1H, 13-H, J 12, 13 = 5.8 Hz), 7.00 d.d (1H, 6-H, J 5, 6 = 7.7, J 4, 6 = 1.5 Hz), 7.29 t (1H, 5-H, J 4, 5 = J 5, 6 = 7.7 Hz), 7.36 d.d (1H, 4-H, J 4, 5 = 7.7, J 4, 6 = 1.5 Hz), 9.45 s (OH). Mass spectrum, m/z (I rel , %): 311 (31) [M] + , ,13b,13c-hexahydro-3aH-furo[3,2-c]isoindolo[2,1-a]quinolin-9(9aH)-one (VIIId) (mixture of trans and cis isomers at a ratio of 1 : 1. Yield 87%, mp 157-158°C (from hexane-ethyl acetate), R f 0.62, 0.91 (hexane-ethyl acetate, 1 : 1). IR spectrum: ν 1691 cm -1 (C=O). 1 H NMR spectrum (CDCl 3 ), δ, ppm: trans isomer: 1.69 s (3H, Me), 1.80 d.d (1H, endo-10-H, J 9a, endo-10 = 9.0, 2 J = 11.8 Hz), 1.86 m (1H, 1-H), 2.07 d.d (1H, exo-10-H, J 9a, exo-10 = 3.5, 2 J = 11.8 Hz), 2.65 m (1H, 1-H), 2.89 m (1H, 13c-H), 3.72 d.d (1H, 9a-H, J 9a, exo-10 = 3.5, J 9a, endo-10 = 9.0 Hz), 3.86-3.95 m (2H, 2-H), 4.42 d (1H, 13b-H, J 13b, 13c = 2.7 Hz), 5.36 d (1H, 3a-H, J 3a,13c = 8.2 Hz), 6.33 d ( 1H, J 12, 13 = 5.7 Hz), 6.54 d (1H, J 12, 13 = 5.7 Hz), 7.17 d.t (1H, J 4, 5 = J 5, 6 = 7.7, J 5, 7 = 1.1 Hz), 7.32 d.d (1H, J 5, 6 = 7.7, J 6, 7 = 8.1 Hz), 7.42 br.d (1H, J 4, 5 = 7.7 Hz), 8.03 d.d (1H, J 5, = 1.1, J 6, 7 = 8.1 Hz); cis isomer: 1.64 s (3H, Me), 1.71 d.d (1H, endo-10-H, J 9a, endo-10 = 8.7, 2 J = 11.8 Hz), 1.86 m (1H, 1-H), 1.99 d.d (1H, exo-10-H, J 9a, exo-10 = 3.6, 2 J = 11.8 Hz), 2.70 m (1H, 1-H), 3.11 m (1H, 13c-H), 3.66 d.d (1H, 9a-H, J 9a, exo-10 = 3.6, J 9a, endo-10 = 8.7 Hz), 3.84 m (2H, 2-H), 4.70 d (1H, 13b-H, J 13b, 13c = 2.5 Hz), 5.24 d (1H, 3a-H, J 3a, 13c = 7.2 Hz), 6.30 d (1H, 13-H, J 12, 13 = 5.7 Hz), 6.44 d (1H, 12-H, J 12, 13 = 5.7 Hz), 7.11 d.t (1H, 5-H, J 4, 5 = J 5, 6 = 7.7, J 5, 7 = 1.1 Hz), 7.24 d.d (1H, 6-H, J 5, 6 = 7.7, J 6, 7 = 8.4 Hz), 7.48 br.d (1H, 4-H, J 4, 5 = 7.7 Hz), 8.66 d.d (1H, 7-H, J 5, 7 = 1.1, J 6, 7 = 8.4 Hz). Mass spectrum, m/z (I rel , %): 309 (18) [M] + ,
Advanced Synthesis & Catalysis, 2006
General comments: Infrared spectra were recorded on a Perkin-Elmer 1720-XFT spectrometer. NMR spectra were recorded on a Bruker DPX-300 instrument at 300
Chemical Communications, 2010
Journal of Chemical Research, 2003
Homophthalic acid (1) and arylcarboxyaldehydes were condensed to form 4-arylideneisochroman-1,3-dione (3) in acetic anhydride in the presence of ammonium acetate under focused microwave irradiation. The stereochemistry of the products was determined by NMR and by X-ray diffraction of one isomer. Table 2 1 H NMR and MS spectra of 4-arylideneisochroman-1,3-dione (3) 3a NMR 1 H (CDCl3, 400 MHz) : E isomer : 3.87, s, 3H, 3H h '; 6.92, d, J = 8.9 Hz, 2H, 2H g '; m, 4H, 2Hf', H a ', H c '; m, 1H, H b '; 8.12, s, 1H, H e '; m, 1H, H d '. 3a NMR 1 H (CDCl 3 , 400 MHz) : Z isomer : 3.89, s, 3H, 3H h ; 6.98, d, J = 8.9 Hz, 2H, 2H g ; 7.46-7.56, m, 1H, Hb; 7.75, ddd, J = 7.8 and J = 1.4 Hz, 1H, H c ; 7.81-7.86, m, 2H, H e and H a ; 7.96, d, J = 9.1 Hz, 2H, 2H f ; 8.18-8.23, m, 1H, Hd. 3a MS : 280 M+. (100); 252 M+. -CO (11); 237 M+ -CO-CH 3 . (10); 193 M+. -CO 2 -CO (19); 165 (28). 3b NMR 1 H (CDCl 3 , 400 MHz) : Z isomer : 6.09, s, 2H, CH 2 ; 6.90, d J = 8.2 Hz, 1H, H g ; 7.35, dd J = 8.0 Hz and J = 2.0 Hz, 1H, H f ; 7.55, ddd J = 8.1 Hz and J = 1.2 Hz, 1H, H c ; 7.65, d, J = 1.7 Hz, 1H, H h ; 7.77, ddd J = 8.2 Hz and J = 1.3 Hz, 1H, H b ; 7.80, d J =7.5 Hz, 1H, H a , 7.78, s, 1H, H e '; 8.23, dd J = 8.6 Hz and J = 1.1 Hz, 1H, H d . 3b MS : 294 M+. (100); 266 M+. -CO (8); 250 M+. -CO 2 (7); 221 M+ -CO 2 -CO -H. (10); 192 M+. -CO -H 2 CO -CO 2 (15); 165 (8). 3c NMR 1 H (CDCl 3 , 250 MHz) : Z isomer : 3.9, s, 3H, 3H i ; 7.11, d J = 8.2 Hz, 1H, H g ; 7.32, dd J = 8.2 Hz and J = 2.2 Hz, 1H, H f ; 7.57, ddd J = 6.8 Hz and J = 1.5 Hz, 1H, H c ; 7.70, d J = 1.9 Hz, 1H, H h ; 7.74-7.84, m, 3H, H b , H a and H e ; 8.23, dd, 1H, J = 7.8 Hz, H d . 3c MS 296 M+. (12). 3d NMR 1 H (CDCl 3 , 400 MHz) : E isomer : 7.08, d, J = 7.9 Hz, 1H, H a '; 7.37-7.47, m, 4H, 2 H f ', H g ' and H c '; 7.53, ddd, J = 1.19 Hz and J = 7.84 Hz, 1H, Hb'; 8.11, s, 1H, H e '; 8.28, dd, 1H, J = 7.9 Hz and J = 1.4Hz, H d '. 3d NMR 1 H (CDCl3, 400 MHz) : Z isomer : 7.29, ddd J = 8.0 Hz and J = 0.67 Hz, 1H, H g ; 7.37-7.47, m, 2H, 2 Hf; 7.66, ddd J = 7.5 Hz and J = 0.9 Hz, 1H, Hc; 7.84, ddd J = 7.6 Hz and J = 1.4 Hz, 1H, Hb; 7.85, s, 1H, He; 8.01, d J = 8.0 Hz, 1H, H a ; 8.31, dd, 1H, J = 7.9 Hz and J = 1.3 Hz, H d . 3d MS : (chemical ionisation with acetonitrile) 319 MH+. (100); 283 M+-Cl. (13). 3e NMR 1 H (DMSO, 400 MHz) : E isomer : 7.65-7.75, m, 3H, H g ', H f ' and H c '; 7.88, ddd J = 8.2 Hz and J = 1.3 Hz, 1H, H b '; 8,01, d J = 1.7 Hz, 1H, H h '; 8.12, dd J = 7.9 Hz and J = 1.2 Hz, 1H, H a '; 8.20, d J = 8.0 Hz, 1H, H d '; 8.32, s, 1H, He'. 3e Z isomer : 7.42, m, 1H, Hb; 7.49, dd J = 8.6 Hz and J = 1.8 Hz, 1H, Hf; 7.54-7.58, m, H c and H a ; 7.65-7.75, m, 1H, H g ; 7.83, d J = 1.5 Hz, 1H, H h ; 8.03, s, 1H, H e ; 8.09, m, 1H, H d .
Contents 1. Ultraviolet Spectroscopy 1 2. Infrared Spectroscopy 26 3. Proton Magnetic Resonance Spectroscopy 64 4. Be NMR Spectroscopy 99 5. Mass Spectrometry 128 6. Structural Data Obtainable from Different Spectra 237 Index
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