References
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- These compounds are being tested for agricultural biological activity: plant growth stimulators, insecticides, herbicides, and fungicides (Dow-Elanco). Other biological screens are expected.
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- Recrystallization of these materials with hydroxylic solvents in a beaker completed the cyclization, and the yellow color usually faded within 5 minutes.
- A small amount of insoluble material sometimes remained, which was removed by filtering (suction) the hot solution.
- Combustion analyses for C, H, and N were obtained from Robertson Laboratory, Inc., 29 Samson Avenue, Madison, NJ 07940, or Quantitative Technologies, Inc., Box 470, Whitehouse, NJ 08888. For Table I: 1, Calcd.: C, 58.04; H, 4.17; N, 14.50. Found: C, 57.98; H, 4.10; N,14.35. 2, Calcd.: C, 51.87; H, 3.42; N, 12.96. Found: C, 51.84; H, 3.39; N, 12.90. 3, Calcd.: C, 50.44; H, 5.64; N, 14.71. Found: C, 50.38; H, 5.54; N, 14.63. 4, Calcd.: C, 44.37; H, 4.14; N, 17.25. Found: C, 44.39; H, 3.93; N, 17.03. For Table II: 5, Calcd.: C, 51.43; H, 5.18; N, 15.99. Found: C, 51.21; H, 5.30; N, 15.83. 6, Calcd.: C, 52.74; H, 5.53; N, 15.38. Found: C, 52.84; H, 5.76; N, 15.27. 7, Calcd.: C, 54.37; H, 4.78; N, 9.06. Found: C, 54.32; H, 4.90; N, 9.09. 8, Calcd.: C, 62.86; H, 5.74; N, 9.56. Found: C, 62.64; H, 5.60; N, 9.41. 9, Calcd.: C, 55.63; H, 4.20; N, 9.73. Found: C, 55.91; H, 4.45; N, 9.62. 10, Calcd.: C, 51.52; H, 3.67; N, 9.01. Found: C, 51.26; H, 3.84; N, 8.76. 11, Calcd.: C, 56.57; H, 4.52; N, 9.42. Found: C, 56.64; H, 4.69; N, 9.25. 12, Calcd.: C, 62.11; H, 5.45; N, 9.88. Found: C, 61.88; H, 5.68; N, 9.61. 13, Calcd.: C, 54.30; H, 4.10; N, 12.66. Found: C, 54.25; H, 4.24; N, 12.56. 14, Calcd.: C, 52.69; H, 5.75; N, 9.22. Found: C, 52.55; H, 5.65; N, 9.27. 15, Calcd.: C, 46.70; H, 4.18; N, 10.89. Found: C, 46.67; H, 4.36; N, 10.69. 16, Calcd.: C, 48.07; H, 4.54; N, 10.51. Found: C, 47.87; H, 4.44; N, 10.37.
- Nuclear magnetic resonance spectra were obtained from a Varian Associates EM 360L NMR Spectrometer, and absorptions are reported in δ ppm downfield from an internal tetramethylsilane (TMS) stadard. Infrared spectra were obtained from a Perkin-Elmer 710-B spectrometer. [Compd No., NMR (δ ppm)/IR (cm−1)] 5, (DMSO-d6): 2.93 (s, N-CH3), 3.30–3.36 (m, CH2C═O), 3.50 and 3.66 (s, OCH3), 6.20 (s, NH2), 6.67–8.00 (m, ArH)/(Nujol): 1670 and 1740 sh (C═O) and 3300 sh and 3500 (NH and NH2). 6, (CDCl3): 1.07 (t, CH3), 2.97–3.10 (m, CH3C═O), 4.00 (q, OCH2), 5.75 (s-broad, NH and/or NH2), and 6.43–7.80 (m, ArH)/(Nujol): 1670, 1720 sh, 1740 (C═O), 3300, 3400, and 3500 (NH and NH2). 7, (DMSO-d6)/CDCl3): 3.20–3.30 (m, CH2C═O), 3.53, 3.70, 3.80 (s, OCH3), 6.87–8.13 (m, ArH), and 10.6 (s, NH)/(Nujol): 1665, 1695, and 1720 (C═O), 3350 and 3500 (NH and OH). 8, (DMSO-d6): 0.97 and 1.07 (t, CH3), 2.40 (s, ArCH3), 3.32 and 3.43 (m, CH2C═O), 3.77–4.37 (m, OCH2), 6.73–8.13 (m, ArH), and 10.38 (s, NH)/(Nujol): 1670, 1710, and 1740 sh (C═O), 3300 and 3350 (NH). 9, (DMSO-d6): 3.40 (s, CH2C═O), 3.50 and 3.70 (s, OCH3), 6.63–8.56 (m, ArH and NH), and 10.53 (s, NH)/(Nujol): 1700, 1720, and 1750 (C═O), 3250 and 3400 (NH). 10, (DMSO-d6): 3.22 and 3.28 (m, CH2C═O), 3.55 and 3.73 (s, OCH3), 6.97–8.13 (m, ArH), and 10.77 (s, NH)/(Nujol): 1670, 1730 sh (C═O), 3350 and 3525 (NH). 11, (DMSO-d6): 3.20 (s, CH2C═O), 3.43 (s, CH2Ar), 3.63 and 3.65 (s, OCH3), 6.87–7.95 (m, ArH and NH), and 10.27 (s, NH)/(Nujol): 1670, 1710, 1740 (C═O), 3320 and 3380 (NH). 12, (DMSO-d6): 2.92 (s, N-CH3), 3.25 and 3.33 (m, CH2C═O), 3.45 (s, CH2Ar), 3.53 (s-sh, OCH3), 6.78–7.95 (s, ArH), and 10.15 (s, NH)/(Nujol): 1680, 1710, 1750 (C═O) and 3310 (NH). 13, (CDCl3/CF3COOH): 3.43–3.48 (m, CH2C═O), 3.68 and 3.80 (s, OCH3), 6.80–8.58 (m, ArH), and 9.88 (s-broad, NH)/(Nujol): 1670 sh and 1720 (C═O), and 3275 and 3350 (NH). 14, (DMSO-D6): 1.12 and 1.20 (t, CH3), 1.43 (s, OC(CH3)3), 3.20 (s, CH2C═O), 3.80 (q, OCH2), 6.90–7.90 (m, ArH and NH), and 8.97 (s, NH)/(Nujol): 1660, 1740, 1760 (C═O), 3280 and 3380 (NH). 15, (DMSO-d6): 3.21 (s, CH2C═O), 3.63 and 3.67 (s, OCH3), 6.83–8.07 (m, ArH and NH), and 9.40 (s, NH)/(Nujol): 1670, 1720, and 1750 sh (C═O), 3250 and 3440 (NH). 16, (DMSO-d6): 1.20 (t, CH3), 3.22 and 3.38 (m, CH2C═O), 3.50 and 3.53 (s, OCH3), 4.14 (q, OCH2), 6.90–8.03 (m, ArH and NH), and 9.93 (s, NH)/(Nujol): 1670, 1720, and 1740 (C═O), 3240 and 3340 (NH).