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Volumn , Issue 19, 2008, Pages 3036-3040

4-(Isoxazol-3-yl)pyrimidines from pyrimidinyl nitrile oxides

Author keywords

2 aminopyrimidine; Cycloaddition; ipso substitution; Isoxazoles; Isoxazolines; Nitrile oxide

Indexed keywords

4 (ISOXAZOL 3 YL)PYRIMIDINE DERIVATIVE; NITRILE OXIDE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 57649131062     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0028-1087346     Document Type: Article
Times cited : (11)

References (36)
  • 29
    • 1442359812 scopus 로고    scopus 로고
    • Note that bleach did not result in oxidation of the 2-(methylthio) pyrimidine moiety. For a related report, see: Tene Ghomsi, J. N.; Ahabchane, H. H.; Essassi, E. M. Phosphorus, Sulfur Silicon Relat. Elem. 2004, 179, 353.
    • Note that bleach did not result in oxidation of the 2-(methylthio) pyrimidine moiety. For a related report, see: Tene Ghomsi, J. N.; Ahabchane, H. H.; Essassi, E. M. Phosphorus, Sulfur Silicon Relat. Elem. 2004, 179, 353.
  • 30
    • 57649126972 scopus 로고    scopus 로고
    • log Kow model developed at Dow AgroSciences
    • unpublished work
    • Demeter, D., log Kow model developed at Dow AgroSciences, unpublished work
    • Demeter, D.1
  • 32
    • 57649124829 scopus 로고    scopus 로고
    • Representative Examples of 5 4-Methyl-6-(5-phenylisoxazol-3-yl)-N-propylpyrimidin-2-amine 1H NMR (300 MHz, CDCl3, δ, 7.80 (m, 2 H, 7.42 (m, 3 H, 7.10 (s, 1 H, 7.00 (s, 1 H, 3.42 (m, 2 H, 2.31 (s, 3 H, 2.18 (s, 1 H, 1.62 (m, 2 H, 0.93 (m, 3 H, 13C NMR (75 MHz, CDCl3, δ, 170.9, 162.9, 162.7, 156.3, 130.6, 129.3, 127.5, 126.1, 106.8, 105.8, 98.7, 43.5, 23.3, 23.1, 11.8. N-(Cyclopropylmethyl)-4-isopropyl-6-(5-phenylisoxazol-3-yl) pyrimidin-2-amine 1H NMR (300 MHz, CDCl3, δ, 7.60 (m, 2 H, 7.24 (m, 3 H, 6.91 (s, 1 H, 6.84 (s, 1 H, 5.22 (br s, 1 H, 3.11 (m, 2 H, 2.64 (m, 1 H, 1.27 (d, J, 7.0 Hz, 6 H, 0.82 (m, 1 H, 0.30 (m, 2 H, 0.05 (m, 2 H, 13C NMR (75 MHz, CDCl3, δ, 178.2, 170.9, 163.6, 162.8, 156.2, 130.6, 129.3, 127.5, 126.1, 104.4, 98.7, 46.8, 36.3, 21.9, 11.9, 3.7. 4-Isopropyl-6-5-phenylisoxazol-3-y
    • 3): δ = 178.2, 170.9, 163.6, 162.8, 156.2, 130.6, 129.3, 127.5, 126.1, 104.4, 98.7, 46.8, 36.3, 21.9, 11.9, 3.7.
  • 33
    • 57649139889 scopus 로고    scopus 로고
    • Representative Examples of 8 N-Cyclopentyl-3-[2-(2- methoxyethylamino)-6-methylpyrimidin-4-yl)isoxazole-5-carboxamide 1H NMR (300 MHz, CDCl3, d, 7.42 (s, 1 H, 7.10 (s, 1 H, 6.55 (br s, 1 H, 5.53 (brs, 1 H, 4.41 (m, 1 H, 3.69-3.55 (m, 4 H, 3.38 (s, 3 H, 2.39 (s, 3 H, 2.13-2.04 (m, 2 H, 1.85-1.52 (m, 6 H, 13C NMR (75 MHz, CDCl3, d, 169.7, 164.3, 163.9, 162.8, 155.5, 154.9, 107.1, 106.2, 71.5, 59.0, 51.9, 41.4, 33.3, 24.4, 24.0. N-Benzyl-3-[2, cyclopentylamino)-6-methylpyrimidin-4-yl]isoxazole-5-carboxamide 1H NMR (300 MHz, CDCl3, δ, 7.49 (s, 1 H, 7.35 (m, 5 H, 7.06 (br s, 2 H, 5.22 (d, J, 6.9 Hz, 1 H, 4.64 (d, J, 6.9 Hz, 2 H, 4.33 (m, 1 H, 2.37 (s, 3 H, 2.04 (m, 2 H, 1.72-1.24 (m, 6 H, 13C NMR 75 MHz, CDCl3, δ, 169.5, 163.9, 162.6, 162.4, 155.9, 154.8, 137.2, 129.1, 129.0, 128.2, 106.7, 106.5, 53.2, 43.8, 3
    • 3): δ = 178.2, 164.1, 163.9, 162.5, 159.6, 155.8, 155.0, 129.7, 129.3, 114.5, 106.6, 104.2, 55.6, 53.3, 43.4, 36.3, 33.5, 24.0, 21.8.
  • 34
    • 57649113323 scopus 로고    scopus 로고
    • General Procedure for Bioassays (a) The primary screen involved two high-throughput insect assays, both incorporating 96-well microtiter plates. The first assay was a 96-well high-throughput bioassay for beet armyworm (Spodoptera exigua: Lepidoptera) larvae, based on modifications of Lewer et al.(2006, Eggs of S. exigua were placed on top of artificial diet (100 mL) in each well of 96-well microtiter plate. The diet had been pretreated with test compounds (12 mg dissolved in 30 mL of DMSO-acetone-H2O mixture) layered on top of the diet using a Sagian (Bechman-Coulter, Fullerton, CA) liquid handling system and then allowed to dry for several hours. Infested plates were then covered with a layer sterile cotton batting and the plate lid, and then held in the dark at 29°C (Lewer et al. 2006, Mortality was recoded at 6 d post-treatment. Each plate had six replicates. The second assay used the yellow fever mosquito Aedes aegypti: Diptera, One-day oid l
    • 2O mixture (90:10)] had been applied (to each of eight wells) and then allowed to dry. Trays were covered with a clear self-adhesive cover, and held at 25°C, 14:10 light/dark for 6 d. Percent mortality was recorded for the larvae in each well; activity in the eight wells was then averaged,


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