References and Notes
<A NAME="RW12107ST-1A">1a</A>
Bistochi GA.
De Meo G.
Pedini M.
Ricci A.
Brouilhet H.
Bucherie S.
Rabaud M.
Jacquignon P.
Farmaco Ed. Sci.
1981,
36:
315
<A NAME="RW12107ST-1B">1b</A>
Picciola G.
Ravenna F.
Carenimi G.
Gentili P.
Riva M.
Farmaco Ed. Sci.
1981,
36:
1037
<A NAME="RW12107ST-2">2</A>
Keppler BK.
Hartmann M.
Met.-Based Drugs
1994,
1:
145
<A NAME="RW12107ST-3A">3a</A>
Sun J.-H.
Teleha CA.
Yan J.-S.
Rodgers JD.
Nugiel DA.
J. Org. Chem.
1997,
62:
5627
<A NAME="RW12107ST-3B">3b</A>
Rodgers JD.
Johnson BL.
Wang H.
Greenberg RA.
Erickson-Viitanen S.
Klabe RM.
Cordova BC.
Rayner MM.
Lam GN.
Chang C.-H.
Bio. Med. Chem. Lett.
1996,
6:
2919
<A NAME="RW12107ST-4">4</A>
Ykeda Y.
Takano N.
Matsushita H.
Shiraki Y.
Koide T.
Nagashima R.
Fujimura Y.
Shindo M.
Suzuki S.
Iwasaki T.
Arzneim. Forsch.
1979,
29:
511
<A NAME="RW12107ST-5">5</A>
Corsi G.
Palazzo G.
Germani C.
Barcellona PS.
Silvestrini B.
J. Med. Chem.
1976,
19:
778
<A NAME="RW12107ST-6">6</A>
Cerecetto H.
Gerpe A.
Gonzalez M.
Aran VJ.
de Ocarizi CO.
Mini-Rev. Med. Chem.
2005,
5:
869
<A NAME="RW12107ST-7">7</A>
Aran VJ.
Ochoa C.
Boiani L.
Buccino P.
Cerecetto H.
Gerpe A.
Gonzalez M.
Montero D.
Nogal JJ.
Gomez-Barrio A.
Azqueta A.
de Cerain AL.
Piro OE.
Castellano EE.
Bioorg. Med. Chem.
2005,
13:
3197
<A NAME="RW12107ST-8">8</A>
Stadlbauer W.
Science of Synthesis
Vol. 12:
Neier RR.
Thieme;
Stuttgart:
2002.
p.227
<A NAME="RW12107ST-9A">9a</A>
Paal C.
Krecke F.
Chem. Ber.
1890,
23:
2640
<A NAME="RW12107ST-9B">9b</A>
Paal C.
Chem. Ber.
1891,
24:
959
<A NAME="RW12107ST-9C">9c</A>
Busch V.
Hartman P.
J. Prakt. Chem.
1895,
2:
404
<A NAME="RW12107ST-9D">9d</A>
Campi EM.
Habsuda J.
Jackson WR.
.
Cartrin AM.
McCubbin QJ.
Aust. J. Chem.
1995,
48:
2023
<A NAME="RW12107ST-10A">10a</A>
Auwers KV.
Schaich W.
Chem. Ber.
1921,
54:
1738
<A NAME="RW12107ST-10B">10b</A>
Albini A.
Bettinetti G.
Minoli G.
Heterocycles
1988,
27:
1207
<A NAME="RW12107ST-10C">10c</A>
Seela F.
Bourgeois W.
Helv. Chim. Acta.
1991,
74:
315
<A NAME="RW12107ST-11A">11a</A>
Cerrada ML.
Elguero J.
de la Fuente J.
Pardo C.
Ramos M.
Synth. Commun.
1993,
23:
1947
<A NAME="RW12107ST-11B">11b</A>
Rosevear J.
Wilshire JFK.
Aust. J. Chem.
1991,
44:
1097
<A NAME="RW12107ST-12A">12a</A>
Cadogan JIG.
Cameron-Wood M.
Mackie RK.
Searle RJG.
J. Chem. Soc.
1965,
4831
<A NAME="RW12107ST-12B">12b</A>
Armour MA.
Cadogan JIG.
Grace DSB.
J. Chem. Soc., Perkin Trans. 1
1975,
1185
<A NAME="RW12107ST-12C">12c</A>
Cadogan JIG.
Mackie RK.
Org. Synth.
1968,
48:
113
<A NAME="RW12107ST-12D">12d</A>
Varughese DJ.
Manhas MS.
Bose AK.
Tetrahedron Lett.
2006,
47:
6795
<A NAME="RW12107ST-13">13</A>
Frontana-Oribe BA.
Moinet C.
Tetrahedron
1998,
54:
3197
<A NAME="RW12107ST-14">14</A>
Akazome M.
Kondo T.
Watanabe Y.
J. Org. Chem.
1994,
59:
3375
<A NAME="RW12107ST-15">15</A>
Song JJ.
Yee NK.
Org. Lett.
2000,
2:
519
<A NAME="RW12107ST-16">16</A>
Mills AD.
Nazer MZ.
Haddadin MJ.
Kurth MJ.
J. Org. Chem.
2006,
71:
2687
<A NAME="RW12107ST-17">17</A>
Kuo CY.
Wu MJ.
J. Chin. Chem. Soc.
2005,
52:
965
<A NAME="RW12107ST-18">18</A>
General Procedure for the Synthesis of 2-Aryl-2
H
-indazoles
A solution of 2-nitrobenzylamine (3 mmol) and SnCl2·2H2O (6 mmol) in 95% EtOH (20 mL) was allowed to stir at 40 °C for 2 h. The reaction
mixture was quenched with 3% HCl (100 mL), filtrated, the crude product was purified
by crystallization from 95% EtOH to give the pure products 2.
<A NAME="RW12107ST-19">19</A>
Representative Spectral Data for 2b
1H NMR (400 MHz, DMSO-d
6): δ = 9.12 (s, 1 H, H-3), 8.10 (d, 2 H, J = 8.0 Hz, ArH), 7.78 (d, 2 H, J = 8.4 Hz, ArH), 7.72 (d, 2 H, J = 8.4 Hz, ArH), 7.46 (t, 1 H, J = 7.2 Hz, ArH), 7.32 (t, 1 H, J = 8.0 Hz, ArH), 7.11 (t, 1 H, J = 7.6 Hz, ArH) ppm. 13C NMR (100 MHz, DMSO-d
6): δ = 149.12, 140.12, 129.86, 128.02, 126.96, 122.64, 122.28, 121.74, 121.11, 120.42,
117.65 ppm. IR (KBr): ν = 3131, 3066, 1626, 1593, 1518, 1494, 1464, 1407, 1378, 1349,
1314, 1250, 1231, 1201, 1143, 1129, 1073, 1044, 950, 907, 820, 780, 754, 685 cm-1. MS: m/z (%) = 194 (100) [M+]. Anal. Calcd for C13H10N2: C, 80.39; H, 5.19; N, 14.42. Found: C, 80.55; H, 5.29; N, 14.26.
<A NAME="RW12107ST-20">20</A>
Crystallographic data for the structure of 2i has been deposited at the Cambridge Crystallographic Data Centre under the deposit
number CCDC-655981. Copies of available material can be obtained free of charge on
application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (1223)336033;
e-mail: deposit@ccdc.cam.ac.uk]. Crystal data for 2i: C14H10Cl2N2; M = 277.14, colorless block crystals, 0.43 × 0.40 × 0.32 mm, monoclinic, space group
P21/c, a = 14.234(3) Å, b = 14.438(3) Å, c = 6.0511(15) Å, α = 90°, β = 92.338(7)°, γ = 90°, V = 1242.5(5) Å3, Z = 4, D
c = 1.481 g cm-1, F(000) = 568, µ (Mo Kα) = 0.503 mm-1. Intensity data were collected on a diffractometer with graphite monochromated Mo
Kα radiation (λ = 0.71073 Å) using ω scan mode with 1.43° < θ < 25.00°; 2183 unique reflections were measured and 1532
reflections with I > 2σ(I) were used in the refinement. The structures were solved by direct methods and expanded
using Fourier techniques. The final cycle of full-matrix least squares technique to
R = 0.0460 and wR = 0.1283.