Ultrasound-assisted synthesis and preliminary bioactivity of novel 2H-1,2,4-thiadiazolo[2,3-a]pyrimidine derivatives containing fluorine

Janeba, 2010, Can. J. Chem., 88, 628, 10.1139/V10-054 Song, 2011, Chin. Chem. Lett., 22, 1036, 10.1016/j.cclet.2011.05.012 P. Raddatz, R. Bergmann, Ger. Patent 3601731, C.A. 109 (1988) 54786. Liu, 2011, Chin. J. Org. Chem. (in Chinese), 31, 1208 Bell, 2006, Org. Process Res. Dev., 10, 1167, 10.1021/op0601518 Okajima, 1991, Pestic. Sci., 32, 91, 10.1002/ps.2780320110 Xue, 2004, Chin. J. Org. Chem. (in Chinese), 24, 1610 Liu, 2008, Pest Manag. Sci., 64, 556, 10.1002/ps.1509 Upadhyay, 2010, J. Pestic. Sci., 35, 464, 10.1584/jpestics.G10-40 Zhou, 2003, Chin. Chem. Lett., 14, 897 Colbert, 1987, Proc. Western Soc. Weed Sci., 40, 155 Pallett, 2001, Pest Manag. Sci., 57, 133, 10.1002/1526-4998(200102)57:2<133::AID-PS276>3.0.CO;2-0 Dabholkar, 2009, J. Heterocycl. Chem., 46, 303, 10.1002/jhet.53 Xu, 1997 J.J. Fuchs, W. Del, U.S. Patent 4,299,960, C.A. 95 (1981) 97120. Analytic data for target compounds. 5a: mp 220–221°C. 1H NMR (400MHz, DMSO-d6): δ 2.32 (s, 3H), 2.53 (s, 3H), 2.72 (s, 3H), 7.03 (s, 1H), 6.80–7.45 (m, 4H). 13C NMR (100MHz, DMSO-d6): δ 169.6, 166.5, 162.7, 161.0, 158.6, 158.1, 152.9, 135.2, 133.9, 132.4, 129.7, 128.0, 125.5, 112.8, 21.4, 20.7, 12.0. Anal. Calcd. for C19H14F3N5O2S: C 52.65, H 3.26, N 16.16; found: C 52.45, H 3.16, N 16.20. 5b: mp 233–234°C. 1H NMR (400MHz, DMSO-d6): δ 2.75 (s, 3H), 3.82 (s, 3H), 3.95 (s, 3H), 5.25 (s, 1H), 6.85–7.45 (m, 4H). 13C NMR (100MHz, DMSO-d6): δ 169.8, 166.4, 162.9, 160.5, 159.1, 158.3, 153.4, 135.5, 133.2, 132.1, 130.5, 128.6, 125.0, 112.7, 55.3, 54.7, 11.8. Anal. Calcd. for C19H14F3N5O4S: C 49.03, H 3.03, N 15.05; found: C 49.43, H 3.01, N 15.36. 5c: mp 240–241°C. 1H NMR (400MHz, DMSO-d6): δ 2.62 (s, 3H), 2.79 (s, 3H), 3.93 (s, 3H), 5.75 (s, 1H), 6.96–7.38 (m, 4H). 13C NMR (100MHz, DMSO-d6): δ 169.9, 166.0, 163.0, 160.6, 159.1, 158.6, 153.1, 134.9, 133.2, 132.1, 130.8, 128.6, 125.0, 112.7, 54.6, 21.4, 11.8. Anal. Calcd. for C19H14F3N5O3S: C 50.78, H 3.14, N 15.58; found: C 50.63, H 3.28, N 15.28. 5d: mp>300°C. 1H NMR (400MHz, DMSO-d6): δ 2.50 (s, 3H), 2.82 (s, 3H), 6.10 (s, 1H), 6.95–7.35 (m, 4H). 13C NMR (100MHz, DMSO-d6): δ 169.7, 165.4, 162.4, 160.5, 158.6, 158.4, 153.6, 135.7, 133.2, 132.3, 130.2, 128.3, 125.3, 113.5, 21.9, 11.8. Anal. Calcd. for C18H12F3N5O3S: C 49.66, H 2.78, N 16.09; found: C 49.48, H 2.52, N 16.18. 5e: mp 252–254°C. 1H NMR (400MHz, DMSO-d6): δ 2.50 (s, 3H), 2.72 (s, 3H), 5.90 (s, 1H), 7.16–7.42 (m, 4H). 13C NMR (100MHz, DMSO-d6): δ 169.7, 165.4, 162.4, 160.5, 158.6, 158.4, 153.6, 135.7, 133.2, 132.4, 130.2, 128.3, 125.3, 113.5, 21.4, 12.2. Anal. Calcd. for C18H11ClF3N5 O2S: C 47.64, H 2.44, N 15.43; found: C 47.54, H 2.45, N 15.32. 5f: mp 242–244°C. 1H NMR (400MHz, DMSO-d6): δ 2.43 (s, 3H), 2.63 (s, 3H), 2.72 (s, 3H), 5.91 (s, 1H), 7.34–7.48 (m, 4H). 13C NMR (100MHz, DMSO-d6): δ 169.8, 165.9, 163.0, 160.4, 159.2, 158.5, 153.6, 135.2, 133.2, 132.1, 130.1, 128.6, 125.1, 112.7, 21.6, 20.4, 11.9. Anal. Calcd. for C19H14F3N5O2S2: C 49.03, H 3.03, N 15.05; found: C 49.23, H 3.19, N 15.33. 5g: mp 255–256°C. 1H NMR (400MHz, DMSO-d6): δ 2.72 (s, 3H), 3.92 (s, 3H), 5.70 (s, 1H), 7.02–7.35 (m, 4H). 13C NMR (100MHz, DMSO-d6): δ 169.9, 166.0, 163.0, 160.6, 159.1, 158.5, 153.4, 135.1, 133.4, 132.1, 130.5, 128.7, 125.0, 112.6, 54.5, 11.9. Anal. Calcd. for C18H11ClF3N5 O3S: C 46.02, H 2.36, N 14.91; found: C 46.11, H 2.36, N 14.87. 5h: mp 228–230°C. 1H NMR (400MHz, DMSO-d6): δ 2.65 (s, 3H), 2.79 (s, 3H), 3.90 (s, 3H), 5.91 (s, 1H), 6.96–7.38 (m, 4H). 13C NMR (100MHz, DMSO-d6): δ 169.8, 165.2, 162.9, 159.6, 159.1, 158.3, 153.0, 135.5, 132.8, 132.1, 130.4, 128.8, 125.1, 112.3, 54.7, 20.6, 12.0. Anal. Calcd. for C19H14F3N5O3S2: C 47.40, H 2.93, N 14.55; found: C 47.50, H 2.85, N 14.42.