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Volumn 38, Issue 7, 2009, Pages 680-681

Pseudo-intramolecular cyclization of α-nitro-δ-keto nitrile leading to 2-amino-3-nitro-1,4-dihydropyridines

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EID: 67650476208     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2009.680     Document Type: Article
Times cited : (9)

References (21)
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    • 43849090178 scopus 로고    scopus 로고
    • Keto nitrile 7 is easily prepared from nitroisoxazolone in one pot, in which intermediate cyano-aci-nitroacetate reacts with only acetone leading to β, β-dimethyl-δ-keto nitrile. Experimental details are shown in the following literature. a N. Nishiwaki, T. Nogami, M. Ariga, Heterocycles 2008, 75, 675.
    • Keto nitrile 7 is easily prepared from nitroisoxazolone in one pot, in which intermediate cyano-aci-nitroacetate reacts with only acetone leading to β, β-dimethyl-δ-keto nitrile. Experimental details are shown in the following literature. a) N. Nishiwaki, T. Nogami, M. Ariga, Heterocycles 2008, 75, 675.
  • 6
    • 84869367559 scopus 로고    scopus 로고
    • To a solution of keto nitrile 7 (92 mg, 0.5 mmol) in acetonitrile (10mL, propylamine (3a, 41 μL, 0.5 mmol) was added. After stirring at room temperature for 10 min, the solvent was evaporated to afford propylammonium salt 8a (122 mg, 0.5 mmol, quant, Pale brown oil. IR (neat/cm -1, 3200-2900 (br, 2198 (strong, 1711, 1341, 1228, 733; 1H NMR (400 MHz, CDCl3, δ 0.99 (t, J=7.4 Hz, 3H, 1.26 (s, 6H, 1.71 (dt, J=7.5, 7.4 Hz, 2H, 2.10 (s, 3H, 2.97 (s, 2H, 3.00 (t, J=7.5 Hz, 2H, 7.2-8.2 (br, 4H, 13C NMR (100 MHz, CDCl3, δ 9.0 (CH3, 19.3 (CH 2, 24.2 (CH3, 29.0 (CH3, 32.3 (CH 2, 39.6 (CH2, 48.6 (CH2, 103.6 (C, 116.1 (C, 206.0 C
    • 2), 103.6 (C). 116.1 (C), 206.0 (C).
  • 8
    • 84869360789 scopus 로고    scopus 로고
    • To a solution of keto nitrile 7 (92 mg, 0.5 mmol) in acetonitrile (10 mL, propylamine (3a, 41 μL, 0.5 mmol) was added, and heated under reflux for 40 h. After removal of the solvent, the residue was treated with column chromatography on silica gel to afford dihydropyridine 9a (eluted with ethyl acetate, 80 mg, 0.35 mmol, 71, Pale yellow needles (from ethyl acetate, Mp 202-204°C. IR (Nujol/cm-1, 1720, 1626, 1535, 1333; 1H NMR (400 MHz, CDCl3, δ 1.01 (t, J=7.2 Hz, 3H, 1.48 (s, 6H, 1.72 (tq, J=7.2, 7.2 Hz, 2H, 1.83 (s, 3H, 3.36 (dt, J=7.2, 5.2Hz, 2H, 4.47 (s, 1H, 7.51 (s, 1H, 12.14 (t, J=5.2 Hz, 1H, 13C NMR (100 MHz, CDCl3, δ 11.4 (CH3, 18.4 (CH3, 22.0 (CH2, 27.0 (CH3, 36.0 (C, 43.5 (CH2, 113.7 (C, 114.4 (CH, 124.7 (C, 152.5 (C, MS (FAB) m/z; 226, M+ 1]+100, Anal. Calcd
    • 2: C. 58.64; H. 8.50; N. 18.65%. Found: C. 58.49; H. 8.51; N. 18.59%.
  • 9
    • 84869340729 scopus 로고    scopus 로고
    • 1H NMR.
    • 1H NMR.
  • 15
    • 67650486914 scopus 로고
    • Chem. Abstr. 1988, 111, 407424.
    • (1988) Chem. Abstr , vol.111 , pp. 407424
  • 17
    • 67650486913 scopus 로고    scopus 로고
    • Chem. Abstr. 1998, 129, 69590.
    • (1998) Chem. Abstr , vol.129 , pp. 69590
  • 21
    • 67650475655 scopus 로고    scopus 로고
    • Supporting Information is available electronically on the CSJ-Journal Web site, http://www.csj.jp/joumals/chem-lett/index.html.
    • Supporting Information is available electronically on the CSJ-Journal Web site, http://www.csj.jp/joumals/chem-lett/index.html.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.