References and Notes
For recent examples, see:
<A NAME="RD35308ST-1A">1a</A>
Taylor RJK.
Reid M.
Foot JS.
Raw SA.
Acc.
Chem. Res.
2005,
38:
851 ;
and references cited therein
<A NAME="RD35308ST-1B">1b</A>
Robinson RS.
Taylor RJK.
Synlett
2005,
1003
<A NAME="RD35308ST-1C">1c</A>
Cayley AN.
Cox RJ.
Ménard-Moyon C.
Schmidt JP.
Taylor RJK.
Tetrahedron Lett.
2007,
48:
6556
<A NAME="RD35308ST-1D">1d</A>
Donald JR.
Edwards MG.
Taylor RJK.
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48:
5201
<A NAME="RD35308ST-2A">2a</A>
Meinwald J.
Labana SS.
Chadha MS.
J. Am. Chem. Soc.
1963,
85:
582
<A NAME="RD35308ST-2B">2b</A> For a review, see:
Rickborn B.
In Comprehensive Organic
Synthesis
Vol. 3:
Trost BM.
Fleming I.
Pattenden G.
Pergamon;
Oxford:
1991.
p.733
For recent examples, see:
<A NAME="RD35308ST-3A">3a</A>
Maruoka K.
Murase N.
Bureau R.
Ooi T.
Yamamoto H.
Tetrahedron
1994,
50:
3663
<A NAME="RD35308ST-3B">3b</A>
Suda K.
Kikkawa T.
Nakajima S.
Takanami T.
J. Am. Chem. Soc.
2004,
126:
9554
<A NAME="RD35308ST-3C">3c</A>
Procopio A.
Dalpozzo R.
De Nino A.
Nardi M.
Sindona G.
Tagarelli A.
Synlett
2004,
2633
For recent examples, see:
<A NAME="RD35308ST-4A">4a</A>
Takanami T.
Hirabe R.
Ueno M.
Hino F.
Suda K.
Chem. Lett.
1996,
1031
<A NAME="RD35308ST-4B">4b</A>
Kulasegaram S.
Kulawiec RJ.
J. Org. Chem.
1997,
62:
6547
For recent examples, see:
<A NAME="RD35308ST-5A">5a</A>
Srikrishna A.
Satyanarayana G.
Prasad KR.
Synth.
Commun.
2007,
37:
1511
<A NAME="RD35308ST-5B">5b</A>
Wilson MS.
Woo JCS.
Dake GR.
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71:
4237
<A NAME="RD35308ST-5C">5c</A>
Vital P.
Tanner D.
Org. Biomol. Chem.
2006,
4:
4292
<A NAME="RD35308ST-5D">5d</A> For a review, see:
Silva LF.
Tetrahedron
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58:
9137 ; and references cited therein
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<A NAME="RD35308ST-6A">6a</A>
Wang L.
Maddess ML.
Lautens M.
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1822
<A NAME="RD35308ST-6B">6b</A>
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Maruoka K.
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2007,
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<A NAME="RD35308ST-6C">6c</A>
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73:
1093
<A NAME="RD35308ST-7">7</A>
D’Ischia M.
Napolitano A.
Pezzella A. In
Comprehensive Heterocyclic Chemistry III
Katritzky
AR.
Ramsden CA.
Scriven EFV.
Taylor RJK.
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p.Chap. 3.04 ; and references therein
For recent reviews, see:
<A NAME="RD35308ST-8A">8a</A>
Hughes DL.
Org. Prep. Proced. Int.
1993,
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607
<A NAME="RD35308ST-8B">8b</A>
Robinson B.
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<A NAME="RD35308ST-9">9</A> See, for example:
Robinson MWC.
Pillinger KS.
Graham AE.
Tetrahedron Lett.
2006,
47:
5919; and references therein
<A NAME="RD35308ST-10">10</A>
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<A NAME="RD35308ST-14">14</A>
All novel compounds were fully characterized.
3-(2′-Benzofuranyl) indole (6a)
Pale orange microcrystals;
mp 162-163 ˚C (heptane); R
f
= 0.27
(PE-Et2O, 4:1). ¹H NMR (400
MHz, CDCl3): δ = 8.33
(br s, 1 H), 8.05-8.00 (m, 1 H), 7.71 (d, J = 2.5
Hz, 1 H), 7.57-7.52 (m, 1 H), 7.49-7.45 (m, 1
H), 7.44-7.39 (m, 1 H), 7.29-7.24 (m, 2 H), 7.23-7.16
(m, 2 H), 6.91 (s, 1 H). ¹³C NMR (100
MHz, CDCl3): δ = 154.0,
152.9, 136.6, 129.9, 124.6, 123.3, 123.12, 123.08, 122.8, 121.1,
120.4, 120.3, 111.7, 110.8, 108.8, 99.7. IR (neat): νmax = 3399, 2918,
2850, 1623, 1453, 1427, 1358, 1249, 1100 cm-¹.
MS (EI+): m/z (%) = 233
(97) [M+
], 135
(38), 97 (37), 95 (50), 93 (37), 91 (52), 83 (37), 81 (63), 79 (50),
71 (51), 69 (71), 67 (100), 57 (73), 55 (91), 43 (48), 41 (52).
HRMS (EI+): m/z calcd
for C16H11NO: 233.0841; Found: 233.0842 [M+
] (0.4 ppm
error).
1-Methyl-3-(2′-benzofuranyl)
indole (6b)
Colourless microcrystals;
mp 109-110 ˚C (i-PrOH); R
f
= 0.44
(PE-Et2O, 7:3). ¹H NMR (400
MHz, CDCl3): δ = 8.06
(dd, J = 8.0,
1.0 Hz, 1 H), 7.62 (s, 1 H), 7.60-7.57 (m, 1 H), 7.54-7.49
(m, 1 H), 7.40 (dd, J = 7.5,
1.5 Hz, 1 H), 7.35 (app. td, J = 7.5,
1.5 Hz, 1 H), 7.31 (app. td, J = 7.5,
1.5 Hz, 1 H), 7.27-7.22 (m, 2 H), 6.91 (d, J = 0.5 Hz,
1 H) 3.85 (s, 3 H). ¹³C NMR (100 MHz,
CDCl3): δ = 154.0,
153.1, 137.5, 130.0, 127.7, 125.1, 123.1, 122.8, 122.6, 120.7, 120.5,
120.1, 110.7, 109.9, 107.0, 99.1, 33.2. IR (neat): νmax = 3053,
2924, 2853, 1624, 1609, 1468, 1452, 1371, 1254, 1203, 1156, 1088,
1014 cm-¹. MS (EI+): m/z (%) = 247 (100) [M+
],
232 (26). HRMS (EI+): m/z calcd
for C17H13NO: 247.0997; found: 247.0987 [M+
] (4.0
ppm error). Anal. Calcd for C17H13NO: C, 82.57;
H, 5.30; N, 5.66. Found: C, 82.39; H, 5.36; N, 5.57.
4,6-Dichloro-3-phenylindole (11)
Orange
oil; R
f
= 0.16
(PE-Et2O, 4:1). ¹H NMR (400
MHz, CDCl3): δ = 8.30
(br s, 1 H), 7.50 (dd, J = 8.0,
1.5 Hz, 2 H), 7.42-7.36 (m, 3 H), 7.34 (d, J = 2.0 Hz,
1 H), 7.19 (d, J = 2.5 Hz,
1 H), 7.15 (d, J = 2.0
Hz, 1 H). ¹³C NMR (100 MHz, CDCl3): δ = 137.5,
134.5, 131.0, 128.1, 127.6, 127.2, 126.9, 124.9, 122.3, 121.9, 119.5,
110.1. IR (neat): νmax = 3417, 3079,
2921, 2851, 1601, 1546, 1474, 1423, 1393, 1188, 1129, 1105, 1076
cm-¹. MS (EI+): m/z (%) = 263
(64) [³7Cl³5ClM+
],
261 (100) [³5Cl³5ClM+
],
199 (25). HRMS (EI+): m/z calcd
for C14H9NCl2: 261.0112; found:
261.0108 [M+
] (1.5
ppm error)].
<A NAME="RD35308ST-15A">15a</A>
Brown DW.
Graupner PR.
Sainsbury M.
Shertzer HG.
Tetrahedron
1991,
47:
4383
<A NAME="RD35308ST-15B">15b</A>
Armit JW.
Robinson R.
J. Chem.
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1922,
121:
827
<A NAME="RD35308ST-16">16</A>
Sanz R.
Castroviejo MP.
Guilarte V.
Pérez A.
Fañanás FJ.
J. Org. Chem.
2007,
72:
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<A NAME="RD35308ST-17">17</A>
Herrmann WA.
Fischer RW.
Marz DW.
Angew. Chem., Int. Ed. Engl.
1991,
30:
1638
