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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 31, 2001 - Issue 22
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Original Articles

CYCLIC HYDROXAMIC ACIDS AS OXYGENATING AGENTS – CONVERSION OF IMINES TO ANILIDES

D. Sahadeva Reddy Department of Chemistry, Osmania University, Hyderabad, 500 007, India
,
P. Pratap Reddy Department of Chemistry, Osmania University, Hyderabad, 500 007, India
&
P. S. N. Reddy Department of Chemistry, Osmania University, Hyderabad, 500007, IndiaCorrespondence[email protected]
Pages 3447-3451 | Received 24 Feb 2000, Published online: 22 Aug 2006

REFERENCES

  • a)The mass spectrum did not record M+. at 70 eV. The highest ion was recorded at m/z 222
  • b) Infrared spectrum showed carbonyl (1684 cm− 1)and NH (3381 cm− 1)
  • c) 1H NMR spectrum is characteristic by the appearance of a singlet at δ 8.4 (the methine hydrogen)
  • a) Infrared spectrum showed absorptions at 3100–2910 cm− 1(br, OH), 1689 (C=O) 1608 (C=N)
  • b) 1H NMR (CDCl3) revealed a methoxyl group (δ 3.9, s, 3H), para disubstituted benzene (δ 6.9, d, J = 11 Hz and δ 7.65, d, J = 11 Hz), quinazolinone peri-proton (δ 8.35, d, 1H, J = 10 Hz) and azomethine proton (δ 8.95, s, 1H); Mass spectrum showed the molecular ion peak at m/z 371
  • 7a: IR (KBr): 3283, 3177, 3130, 3060, 1671 (br), 1605, 1575, 1536, 1468, 1279, 946 cm− 1; 1H NMR (DMSO-d6): δ 3.9 (s, 3H, OCH3), 7.0–8.2 (m, 11H, Ar-H), 8.65 (d, 1H, J = 10 Hz, Peri Ar-H), D2O exchangeable signals at 12.5 (s, NH) and 12.7 (s, NH). MS m/z 371 (M+), 369, 353, 135, 107, 92, 77, 64
  • 7b: IR (KBr): 3261, 3180, 3130, 3064, 1683 (br), 1603, 1560, 1525, 1445, 1276, 949 cm− 1; 1H NMR (DMSO-d6): δ 7.3–8.3 (m, 12H, Ar-H), 8.6 (d, 1H, J = 10 Hz, peri Ar-H), 12.0 (s, NH), 12.4 (s, NH); MS m/z 341 (M+), 323, 294, 264, 162, 105, 77
  • 7c: IR (KBr): 3271, 3128, 3060, 1685 (br), 1605, 1540, 1496, 1405, 1276, 949 cm−1; 1H NMR (DMSO-d6): δ 7.2–8.2 (m, 11H, Ar-H), 8.5 (d, 1H, J = 10 Hz, peri Ar-H), 12.2 (s, NH) 12.5 (s, NH); MS m/z 375 (M+), 357, 325, 135, 111, 77
  • 7d: IR (KBr): 3254, 3189, 3058, 1686 (br), 1602, 1576, 1519, 1445, 1279, 947 cm−1; 1H NMR (DMSO-d6): δ 7.25–8.25 (m, 11H, Ar-H), 8.6 (d, 1H, J = 10 Hz, peri Ar-H), 12.24 (s, NH), 12.45 (s, NH); MS m/z 386 (M+), 368, 264, 150, 123, 119, 77
  • Butler , K. , Partridge , M. W. and Waite , J. A. 1960 . J. Chem. Soc. , : 4970
  • Katrizky , A. R. and Brown , S. B. 1978 . Synthesis , : 619
  • Cook , M. J. , Katrizky , A. R. and Millet , G. H. 1977 . Heterocycles , 7 : 227
  • Katrizky , A. R. , Cook , M. J. , Brown , S. B. , Cruz , R. and Millet , G. H. 1979 . J. Chem. Soc. Perkin Trans 1 , : 2493
  • Emmons , W. D. 1957 . J. Am. Chem. Soc. , 79 : 5739

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