ACS Combinatorial Science
Research Article
Alvarez-Builla, J.; Vaquero, J. J. Reaction of bromomethylazoles and
tosylmethyl isocyanide. A novel heterocyclization method for the
synthesis of the core of marine alkaloids variolins and related
azolopyrimidines. J. Org. Chem. 2004, 69, 4974−4983.
(C-3′, C-4′, C-5′, C-6′), 129.8 (C-6), 131.3 (C-2″, C-6″), 131.5,
136.4, 137.9, 140.0 (C-4a, C-1′, C-2′, C-1″), 140.3 (C-1), 152.4
(C-3), 163.1 (COO), 164.0 (C-4″), 184.2 (COAr); Anal. Calcd
C24H20N2O4 C 71.99, H 5.03, N 7.0; Found C 72.35, H 5.22, N
6.89.
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Ethyl 3-(2-Methylphenyl)-7-(4-fluorobenzoyl)pyrrolo[1,2-
c]pyrimidine-5-carboxylate 4{1,5,1}: Pale yellow crystals; IR
1
(cm−1) 1696, 1622, 1600, 1523, 1476, 1327, 1222, 1203; H
NMR (300 MHz, CDCl3) δ 1.40 (t, 3H, J = 7.1 Hz, Me), 2.52
(s, 3H, 2′-Me), 4.40 (q, 2H, J = 7.1 Hz, CH2), 7.24 (t, 2H, J =
8.6 Hz, H-3″, H-5″), 7.33−7.36 (m, 3H, H-3′, H-4′, H-5′),
7.58−7.61 (m, 1H, H-6′), 7.86 (s, 1H, H-6), 7.90 (dd, 2H, J =
5.4, 8.6 Hz, H-2″, H-6″), 8.34 (d, 1H, J = 1.5 Hz, H-4), 10.60
(d, 1H, J = 1.5 Hz, H-1); 13C NMR (75 MHz, CDCl3) δ 14.5
(Me), 20.7 (2′-Me), 60.5 (CH2), 107.0 (C-4), 113.0 (C-5),
115.7 (d, J = 22.0 Hz, C-3″, C-5″), 122.0 (C-7), 126.2, 129.2,
129.6, 131.2 (C-3′, C-4′, C-5′, C-6′), 129.8 (C-6), 131.4 (d, J =
8.9 Hz, C-2″, C-6″), 135.1 136.3, 137.7, 140.2 (C-4a, C-1′, C-2′,
C-1″), 140.3 (C-1), 152.6 (C-3), 163.5 (COO), 165.1 (d, J =
250 Hz, C-4″), 183.8 (COAr); Anal. Calcd C24H19FN2O3 C
71.63, H 4.76, N 6.96; Found C 71.42, H 4.92, N 7.12.
ASSOCIATED CONTENT
* Supporting Information
■
S
Experimental details and spectroscopic characterization are
presented for compounds 1{1}, 1{2}, 1{4}, 1{9}, 1{10}, com-
pounds 4 and 5 and tabulated improved Lipinski’s rule parameters
and property distributions. This material is available free of charge
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AUTHOR INFORMATION
Corresponding Author
Author Contributions
EG., F.G., and F.D. conceived and designed experiments, E.G.,
F.G., M.M.P., and F.D. performed the experiments, analysis,
and cowrote the manuscript and Supporting Information,
C.D. performed all NMR spectra and cowrote the Supporting
Information, and L.T. calculated and evaluated the Lipinski’s
rule parameters.
■
Notes
The authors declare no competing financial interest.
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