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Volumn 36, Issue 8, 2007, Pages 1074-1075

A facile and convenient synthesis of N-acetyl-2-aryl-1,2-dihydro-(4H)-3,1- benzoxazin-4-ones from the reaction of anthranilic acid derivatives with aryl aldehydes

(3) Nikpour, Farzad a Sheikh, Davood a Saraji, Mohammad b

a UNIVERSITY OF KURDISTAN (Iran)

b ISFAHAN UNIVERSITY OF TECHNOLOGY (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34548299421 PISSN: 03667022 EISSN: None Source Type: Journal
DOI: 10.1246/cl.2007.1074 Document Type: Article

Times cited : (8)

References (20)

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12
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- The compounds of this type can be ring opened by nucleophiles such as cyanide ion and the resulting N-cyanomethylanthranilic acids are potential starting material for synthesis of important heterocycles as 1,4-benzodiazepine-2,5-diones and 2-cyanoindoxyls: a N. J. Hrib, J. G. Jurcut, D. E. Bregna, K. L. Burgher, H. B. Hartman, S. Kafca, L. L. Kerman, S. Kongsamut, J. E. Roehr, M. R. Szewczak, A. T. Woods-Kettelgerger, R. Corbett, J. Med. Chem. 1996, 39, 40444
- The compounds of this type can be ring opened by nucleophiles such as cyanide ion and the resulting N-cyanomethylanthranilic acids are potential starting material for synthesis of important heterocycles as 1,4-benzodiazepine-2,5-diones and 2-cyanoindoxyls: a) N. J. Hrib, J. G. Jurcut, D. E. Bregna, K. L. Burgher, H. B. Hartman, S. Kafca, L. L. Kerman, S. Kongsamut, J. E. Roehr, M. R. Szewczak, A. T. Woods-Kettelgerger, R. Corbett, J. Med. Chem. 1996, 39, 40444.

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15
- 34548366778
- Substances were purchased commercially and used without more purification. General reaction procedure: A mixture of 0.001 mol of an anthranilic acid derivative 1 and 0.0012 mol of an aryl aldehyde 2 was stirred in methanol for about 1 h at room temperature. The solvent was removed and then, the mixture was refluxed in 3 mL of acetic anhydride for the times as indicated in Table 1. After removal of the residue of acetic anhydride, the precipitate was washed with 3 mL of cold-water (three times) and filtered. The obtained products were dried in air and crystallized from methanol or ethanol. All new compounds afforded spectroscopic data. Selected spectral data: Entry 6: Pale yellow crystals from ethanol, mp 137-139 °C IR (KBr, ν (cm-1) 1739, 1691. 1HNMR (250.1 MHz) in CDCl3: δ 7.95 (s, 1H, arom. H, 7.61-7.50 (m, 2H, arom. H, 7.41(s, 1H, CH, 7.25-7.23 (m, 4H, arom. H, 2.51 (s, 3H, CH3, 13CNMR (62.9 MHz) in CDC
- +, 25).

16
- 34548345053
- Entry 9: White crystals from methanol, mp 165-168°C IR (KBr, ν (cm-1) 1764, 1739, 1709, 1583, 1349. 1HNMR (250.1 MHz) in CDCl3: δ 8.12 (s, 1H, arom. H, 7.74-7.71 (m, 2H, arom. H, 7.55-7.38 (m, 4H, arom. H, 7.52 (s, 1H, CH, 2.79 (s, 1H, CH3COO, 2.27 (s, 3H, CH3CON, 13C NMR (62.9MHz) in CDCl 3: δ 170.0, 168.6, 161.0, 148.6, 148.3, 138.2, 136.1, 132.2, 130.2, 128.7, 125.2, 124.2, 123.3, 121.0, 120.9, 82.6, 22.5, 20.9. MS (EI, m/z, ) 370 (M, 10, 328 (M, H2C=C=O, 45, 286 (C14H10N2O5, 100, 241 (C13H9N2O3, 44, 195 (C13H9NO, 32, 177 (C 13H7N, 35, 135 C7H 3O3, 86
- +, 86).

17
- 34548366779
- Entry 11: Pale crystals from n-hexane/ethanol, mp 200-202°C. IR (KBr, ν (cm-1) 1717, 1687, 1524, 1340. 1H NMR (250.1 MHz) in CDCl3: δ 8.13 (s, 1H, arom. H, 7.74-7.66 (m, 3H, arom. H, 7.51 (s, 1H, CH, 7.30 (s, 1H, arom. H, 6.90 (s, 1H, arom. H, 3.94 and 3.83 (2s, 6H, 2CH3O, 2.49 (s, 3H, CH3, 13CNMR (62.9MHz) in CDCl3: δ 170.1, 161.0, 154.6, 148.5, 147.9, 138.7, 133.1, 132.2, 130.1, 123.9, 120.9, 111.8, 110.6, 106.8, 82.5, 56.6, 56.2, 22.7. MS (EI, m/z, ) 372 (M, 55, 330 (M, H2C=C=O, 100, 285 (M, H2C=C=O, COOH, 51, 221 (C11H11NO4, 56, 206 (C 10H8NO4, 33, 179 C 9H9NO3, 55
- +, 55).

18
- 34548353225
- Entry 12: Pale crystals from methanol, mp 215-218°C IR (KBr, ν (cm-1) 3450-2250, 1735, 1700, 1685. 1H NMR (250.1 MHz) in CDCl3: δ 11.23 (bs, 1H, COOH, 8.11-7.83 (m, 3H, arom. H, 7.31 (s, 1H, CH, 7.28-7.21 (m, 4H, arom. H, 2.50 (s, 3H, CH3, 13CNMR (62.9MHz) in CDCl3: δ 171.1, 168.4, 162.4, 138.2, 136.2, 135.6, 132.1, 132.0, 130.6, 128.5, 127.3, 126.9, 126.0, 124.6, 123.4, 82.6, 22.6. MS (EI, m/z, ) 347, M, 2, 2, 345 (M, 5, 305, M, 2, H2C=C=O, 22, 304, M, 2, H2C=C=O, H, 30, 303, M, 2, H2C=C=O, 80, 302 (M+ H2C=C=O, H, 71, 261 (C14H1037Cl NO2, 8, 259 (C14H1035ClN02, 23, 163 C 8H5NO3, 100
- +, 100).

19
- 34548341038
- Entry 17: Pale yellow crystals from n-hexane/ethanol, mp 172-175°C IR (KBr, ν (cm-1) 1720, 1684. 1H NMR (250.1 MHz) in CDCl3: δ 7.47 (s, 1H, arom. H, 7.45-7.30 (m, 3H, arom. H and CH, 6.94 (s, 1H, arom. H, 6.90-6.82 (m, 2H, arom. H, 3.98, 3.95, and 3.87 (3s, 9H, 3CH3O, 2.43 (s, 3H, CH3, 13C NMR (62.9 MHz) in CDCl3: δ 159.6, 159.5, 159.4, 156.4, 156.3, 149.5, 149.0, 142.8, 125.3, 125.2, 120.1, 111.2, 109.0, 107.3, 82.3, 56.4, 56.3, 56.2, 21.2. MS (EI, m/z, ) 357 (M, 42, 315 (M, H2C=C=O, 100, 270 (M, H2C=C=O, COOH, 57, 206 (C10H8NO4, 39, 179 (C9H9NO3, 48, 107 C 7H7O, 64
- +, 64).

20
- 34548328619
- Entry 19: White crystals from n-hexane/ethanol, mp 80-82°C IR (KBr, ν(cm-1) 1763, 1742, 1689. 1H NMR (250.1 MHz) in CDCl3: δ 8.12 (d, 47HH, 2.5 Hz, 1H, arom. H, 7.63 (dd, 3JHH, 8.7 Hz, 4J HH, 2.5 Hz, 1H, arom. H, 7.33-7.08 (m, 5H, arom. H and CH, 6.99 (d, 3JHH, 8.7 Hz, 1H, arom. H, 2.33 (s, 1H, CH 3COO, 2.30 (s, 3H, CH3CON, 13C NMR (62.9 MHz) in CDCl3: δ 169.5, 168.8, 160.7, 148.4, 148.3, 137.6, 137.3, 132.5, 130.6, 127.4, 126.3, 126.0, 123.9, 121.8, 120.2, 82.3, 22.3, 21.0. MS (EI, m/z, ) 405, M, 2, 3, 403 (M, 4, 361, M, 2, H2C=C=O, 45, 359 (M, H 2C=C=O, 45, 319, M, 2, 2H2C=C=O, 99, 315 (M, 2H2C=C=O, 100, 199 C7H 481
- +, 65).

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