-
2
-
-
43849096211
-
-
Y. Nakaike, N. Taba, S. Itoh, Y. Tobe, N. Nishiwaki, M. Ariga, Bull. Chem. Soc. Jpn. 2007, 80, 2413.
-
(2007)
Bull. Chem. Soc. Jpn
, vol.80
, pp. 2413
-
-
Nakaike, Y.1
Taba, N.2
Itoh, S.3
Tobe, Y.4
Nishiwaki, N.5
Ariga, M.6
-
3
-
-
0242383937
-
-
N. Nishiwaki, D. Nishida, T. Ohnishi, F. Hidaka, S. Shimizu, M. Tamura, K. Hori, Y. Tohda, M. Ariga, J. Org. Chem. 2003, 68, 8650.
-
(2003)
J. Org. Chem
, vol.68
, pp. 8650
-
-
Nishiwaki, N.1
Nishida, D.2
Ohnishi, T.3
Hidaka, F.4
Shimizu, S.5
Tamura, M.6
Hori, K.7
Tohda, Y.8
Ariga, M.9
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4
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43849090178
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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.
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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.
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5
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0033583005
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N. Nishiwaki, T. Nogami, C. Tanaka, F. Nakashima, Y. Inoue, N. Asaka, Y. Tohda, M. Ariga, J. Org. Chem. 1999, 64, 2160.
-
(1999)
J. Org. Chem
, vol.64
, pp. 2160
-
-
Nishiwaki, N.1
Nogami, T.2
Tanaka, C.3
Nakashima, F.4
Inoue, Y.5
Asaka, N.6
Tohda, Y.7
Ariga, M.8
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6
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84869367559
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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
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2), 103.6 (C). 116.1 (C), 206.0 (C).
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7
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84993844919
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N. Nishiwaki, Y. Takada, Y. Inoue, Y. Tohda, M. Ariga, J. Heterocycl. Chem. 1995, 32, 473.
-
(1995)
J. Heterocycl. Chem
, vol.32
, pp. 473
-
-
Nishiwaki, N.1
Takada, Y.2
Inoue, Y.3
Tohda, Y.4
Ariga, M.5
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8
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-
84869360789
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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
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2: C. 58.64; H. 8.50; N. 18.65%. Found: C. 58.49; H. 8.51; N. 18.59%.
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9
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84869340729
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1H NMR.
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1H NMR.
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12
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0030219592
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M. S. Wong, C. Bosshard, F. Pan, P. Günter, Adv. Mater. 1996, 8, 677.
-
(1996)
Adv. Mater
, vol.8
, pp. 677
-
-
Wong, M.S.1
Bosshard, C.2
Pan, F.3
Günter, P.4
-
13
-
-
0001787360
-
-
W. Schuddeboom, B. Krijnen, J. W. Verhoeven, E. G. J. Staring, G. L. J. A. Rikken, H. Oevering, Chem. Phys. Lett. 1991, 179, 73.
-
(1991)
Chem. Phys. Lett
, vol.179
, pp. 73
-
-
Schuddeboom, W.1
Krijnen, B.2
Verhoeven, J.W.3
Staring, E.G.J.4
Rikken, G.L.J.A.5
Oevering, H.6
-
14
-
-
67650484012
-
-
Eur. Pat. Appl. EP 296, 453, 1988;
-
K. Shiokawa, S. Tsuboi, S. Sasaki, K. Moriya, Y. Hattori, K. Shibuya, Eur. Pat. Appl. EP 296, 453, 1988;
-
-
-
Shiokawa, K.1
Tsuboi, S.2
Sasaki, S.3
Moriya, K.4
Hattori, Y.5
Shibuya, K.6
-
15
-
-
67650486914
-
-
Chem. Abstr. 1988, 111, 407424.
-
(1988)
Chem. Abstr
, vol.111
, pp. 407424
-
-
-
16
-
-
67650496319
-
-
K. Urbahns, S. Goldmann, H.-G. Heine, B. Junge, R. Schohe-Loop, H. Sommemeyer, T. Glaser, R. Wittka, J. de Vry, Ger. Offen. DE 4, 430, 095, 1996;
-
(1996)
Ger. Offen
, vol.DE 4
, Issue.430
, pp. 095
-
-
Urbahns, K.1
Goldmann, S.2
Heine, H.-G.3
Junge, B.4
Schohe-Loop, R.5
Sommemeyer, H.6
Glaser, T.7
Wittka, R.8
de Vry, J.9
-
17
-
-
67650486913
-
-
Chem. Abstr. 1998, 129, 69590.
-
(1998)
Chem. Abstr
, vol.129
, pp. 69590
-
-
-
18
-
-
0037033239
-
-
a) V. J. Ram, N. Agarwal, A. Sharon, P. R. Maulik, Tetrahedron Lett. 2002, 43, 307.
-
(2002)
Tetrahedron Lett
, vol.43
, pp. 307
-
-
Ram, V.J.1
Agarwal, N.2
Sharon, A.3
Maulik, P.R.4
-
19
-
-
0027280660
-
-
R. Troschütz, A. Lückel, H. Mertens, Arch. Pharm. 1993, 326, 335.
-
(1993)
Arch. Pharm
, vol.326
, pp. 335
-
-
Troschütz, R.1
Lückel, A.2
Mertens, H.3
-
21
-
-
67650475655
-
-
Supporting Information is available electronically on the CSJ-Journal Web site, http://www.csj.jp/joumals/chem-lett/index.html.
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Supporting Information is available electronically on the CSJ-Journal Web site, http://www.csj.jp/joumals/chem-lett/index.html.
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