References
<A NAME="RD17202ST-1A">1a</A>
Curtius T.
Berichte
1883,
16:
2230
<A NAME="RD17202ST-1B">1b</A>
Curtius T.
J. Prakt.
Chem.
1888,
38:
396
<A NAME="RD17202ST-2">2</A>
Doyle MP.
McKervey MA.
Ye T.
Modern
Catalytic Methods for Organic Synthesis with Diazo Compounds. From
Cyclopropanes to Ylides
Wiley-Interscience;
New York:
1998.
<A NAME="RD17202ST-3A">3a</A>
Padwa A.
J. Organomet. Chem.
2001,
617-618:
3
<A NAME="RD17202ST-3B">3b</A>
Doyle MP.
Forbes DC.
Chem.
Rev.
1998,
98: 911
<A NAME="RD17202ST-3C">3c</A>
Doyle MP.
McKervey MA.
Chem.
Commun.
1997,
983
<A NAME="RD17202ST-3D">3d</A>
Padwa A.
Weingarten MD.
Chem. Rev.
1996,
96:
223
<A NAME="RD17202ST-3E">3e</A>
Miller DJ.
Moody CJ.
Tetrahedron
1995,
51:
10811
<A NAME="RD17202ST-3F">3f</A>
Padwa A.
Austin DJ.
Angew. Chem., Int.
Ed. Engl.
1994,
33:
1797
<A NAME="RD17202ST-3G">3g</A>
Doyle MP.
Chem. Rev.
1986,
86:
919
<A NAME="RD17202ST-4">4</A>
Ye T.
McKervey MA.
Chem. Rev.
1994,
94:
1091
<A NAME="RD17202ST-5A">5a</A>
Doyle MP.
Kalinin AV.
Tetrahedron Lett.
1996,
37:
1371
<A NAME="RD17202ST-5B">5b</A>
Bode JW.
Doyle MP.
Protopopova MN.
Zhou QL.
J.
Org. Chem.
1996,
61:
9146
<A NAME="RD17202ST-5C">5c</A>
Taber DF.
Song Y.
J. Org. Chem.
1996,
61:
6706
<A NAME="RD17202ST-5D">5d</A>
Wee AGH.
Liu B.
Tetrahedron
Lett.
1996,
37:
145
<A NAME="RD17202ST-6">6</A>
Muthusamy S.
Gunanathan C.
Babu SA.
Suresh E.
Dastidar P.
Chem.
Commun.
2002,
824
<A NAME="RD17202ST-7A">7a</A>
Maryanoff BE.
J. Org. Chem.
1982,
47:
3000
<A NAME="RD17202ST-7B">7b</A>
Demonceau A.
Noels AF.
Hubert AJ.
Teyssie P.
J. Chem.
Soc., Chem. Commun.
1981,
688
<A NAME="RD17202ST-7C">7c</A>
Maryanoff BE.
J. Org. Chem.
1979,
44:
4410
<A NAME="RD17202ST-7D">7d</A>
Maryanoff BE.
J. Heterocycl. Chem.
1977,
14:
177
<A NAME="RD17202ST-8A">8a</A>
Pirrung MC.
Florian B.
J.
Org. Chem.
1999,
64:
3642
<A NAME="RD17202ST-8B">8b</A>
Pirrung MC.
Zhang J.
McPhail AT.
J. Org. Chem.
1991,
56:
6269
<A NAME="RD17202ST-9A">9a</A>
Muthusamy S.
Gunanathan C.
Babu SA.
Synthesis
2002,
471
<A NAME="RD17202ST-9B">9b</A>
Muthusamy S.
Babu SA.
Gunanathan C.
Jasra RV.
Synlett
2002,
407
<A NAME="RD17202ST-9C">9c</A>
Muthusamy S.
Babu SA.
Gunanathan C.
Suresh E.
Dastidar P.
Bull.
Chem. Soc. Jpn.
2002,
75:
801
<A NAME="RD17202ST-9D">9d</A>
Muthusamy S.
Babu SA.
Gunanathan C.
Tetrahedron
Lett.
2002,
43:
3931
<A NAME="RD17202ST-9E">9e</A>
Muthusamy S.
Babu SA.
Gunanathan C.
Tetrahedron
Lett.
2002,
43:
5981
<A NAME="RD17202ST-9F">9f</A>
Muthusamy S.
Gunanathan C.
Babu SA.
Tetrahedron
Lett.
2001,
42:
523
<A NAME="RD17202ST-10">10</A>
Cava MP.
Little RL.
Naipier DR.
J. Am. Chem. Soc.
1958,
80:
2257
<A NAME="RD17202ST-11">11</A>
Heaney H.
Ley SV.
J. Chem. Soc., Perkin
Trans 1
1973,
499
<A NAME="RD17202ST-12">12</A>
General Procedure
for the Synthesis of 2-Pyrrol-3′-yloxindoles: In an
oven-dried flask, a solution containing 1.2 equiv of pyrrole and
1 mol% of rhodium(II) acetate dimer in 10 mL of dry dichloromethane
(dried over phosphorous pentoxide) was degasified under an argon atmosphere.
To this reaction mixture, a solution of 1 equiv of appropriate cyclic
diazoamide in dry dichloromethane was added dropwise slowly for
1 h period under an argon atmosphere at r.t. The reaction mixture
was allowed to stir and followed by TLC till the disappearance of
the starting material. The solvent was removed under reduced pressure and
the residue purified by flash silica gel column chromatography to
afford the respective C-H insertion products.
<A NAME="RD17202ST-13">13</A>
All new compounds exhibited spectral
data consistent with their structures. Selected spectral data: 3-(1-Benzyl-1
H
-pyrrol-2-yl)-1-methyl-1,3-dihydro-indol-2-one
(3a): Colorless solid. Mp 115-117 °C
(hexane/EtOAc). IR (KBr): 2932, 1716, 1609, 1490, 1464,
1368, 1345, 1302, 1253, 1180, 1085, 714 cm-1. 1H
NMR (200 MHz, CDCl3): δ = 3.09 (s,
3 H, N-CH3), 4.55 (s, 1 H), 5.14 (d, 1 H, J = 16.3 Hz), 5.51
(d, 1 H, J = 16.3
Hz), 5.78-5.80 (m, 1 H), 6.09 (t, 1 H, J = 2.5
Hz), 6.69 (t, 1 H, J = 2.5
Hz), 6.79 (d, 1 H, J = 7.7 Hz),
6.97-7.04 (m, 3 H), 7.12-7.33 (m, 5 H). 13C
NMR (50.3 MHz, CDCl3): δ = 26.9
(N-CH3) 45.1 (CH), 51.7 (N-CH2), 108.0 (CH),
108.7 (CH), 109.3 (CH), 123.2 (CH), 124.0 (CH), 125.7 (CH), 126.1
(quat-C), 127.2 (CH), 127.7 (CH), 128.0
(quat-C), 128.1 (CH), 128.9 (CH), 129.3
(CH), 138.9 (quat-C), 144.9 (quat-C), 175.4 (quat-C).
MS: m/z = 302 (38.5) [M+],
212 (23.7), 211(100), 168 (14.3), 157 (17.6), 156 (94.5), 154(13),
91(84). Anal. Calcd for C20H18N2O:
C, 79.44; H, 6.00; N, 9.26. Found: C, 79.26; H, 5.98; N, 9.23.
3-(1-Benzyl-1
H
-pyrrol-3-yl)-1-methyl-1,3-dihydro-indol-2-
one (4a): Colorless solid. Mp 96-98 °C
(hexane/EtOAc). IR (KBr): 2928, 1718, 1627, 1469, 1463,
1368, 1355, 1309, 1263, 1187, 1066, 720 cm-1. 1H
NMR (200 MHz, CDCl3): δ = 3.18
(s, 3 H, N-CH3), 4.56 (s, 1 H), 4.99 (s, 2 H, N-CH2),
6.11 (t, 1 H, J = 2.2
Hz), 6.61-6.73 (m, 2 H), 6.93 (d, 1 H, J = 7.1
Hz), 7.05-7.36 (m, 8 H). MS:
m/z = 212 [M+].
Anal. Calcd for C20H18N2O: C, 79.44;
H, 6.00; N, 9.26. Found: C, 79.19; H, 6.02; N, 9.29.
1-Methyl-3-[1-(4-methyl-benzyl)-1
H
-pyrrol-2-yl]-1,3-dihydro-indol-2-one
(3f): Colorless oil. IR (neat): 2983, 1713, 1613, 1493, 1470,
1421, 1372, 1349, 1305, 1265, 1125, 1086, 740 cm-1. 1H
NMR (200 MHz, CDCl3): δ = 2.29 (s,
3 H, ArCH3), 3.09 (s, 3 H, N-CH3), 4.55 (s,
1 H), 5.10 (d, 1 H, J = 16.1
Hz), 5.46 (d, 1 H, J = 16.1
Hz), 5.77 (t, 1 H, J = 1.7
Hz), 6.07 (t, 1 H, J = 2.9
Hz), 6.67 (t, 1 H, J = 1.7 Hz),
6.77 (d, 1 H, J = 7.8
Hz), 6.99-7.29 (m, 7 H). 13C
NMR (50.3 MHz, CDCl3): δ = 21.8
(CH3), 27.0 (CH3,) 45.2 (CH), 51.6 (N-CH2),
107.9 (CH), 108.7 (CH), 109.3 (CH), 123.2 (CH), 124.0 (CH), 125.7
(CH), 127.3 (CH), 128.3 (quat-C), 129.0
(CH), 130.0 (CH), 135.8 (quat-C), 137.7
(quat-C), 145.0 (quat-C),
175.4 (quat-C). MS: m/z = 316 [M+].
Anal. Calcd for C21H20N2O: C, 79.72;
H, 6.37; N, 8.85. Found: C, 79.92; H, 6.35; N, 8.82.
1-Methyl-3-[1-(4-methyl-benzyl)-1
H
-pyrrol-3-yl]-1,3-dihydro-indol-2-one
(4f): Colorless oil. IR (neat): 2965, 1715, 1612, 1486, 1467,
1451, 1363, 1347, 1320, 1280, 1116, 1085, 735 cm-1. 1H
NMR (200 MHz, CDCl3): δ = 2.26 (s,
3 H, ArCH3), 3.19 (s, 3 H, N-CH3), 4.55 (s,
1 H), 4.94 (s, 2 H, N-CH2), 6.10 (t, 1 H, J = 2.4 Hz),
6.59-6.64 (m, 2 H), 6.83 (d, 1 H, J = 7.4Hz),
7.01-7.17 (m, 5 H), 7.26-7.32 (m, 2 H). MS: m/z = 316 [M+].
Anal. Calcd for C21H20N2O: C, 79.72;
H, 6.37; N, 8.85. Found: C, 79.89; H, 6.39; N, 8.87.
3-[1-(3,5-Dimethyl-benzyl)-1
H
-pyrrol-2-yl]-1-methyl-1,3-dihydro-indol-2-one
(3k): Gray color solid. Mp 156-158 °C
(hexane/EtOAc). IR (KBr): 2920, 1717, 1609, 1492, 1467,
1372, 1343, 1304, 1127, 1086, 843, 750 cm-1. 1H NMR
(200 MHz, CDCl3): δ = 2.25
(s, 6 H, ArCH3), 3.13 (s, 3 H, N-CH3), 4.59
(s, 1 H), 5.07 (d, 1 H, J = 16.2
Hz), 5.45 (d, 1 H, J = 16.2
Hz), 5.79 (t, 1 H, J = 1.8
Hz), 6.09 (t, 1 H, J = 2.9
Hz), 6.64 (s, 2 H), 6.69 (t, 1 H, J = 1.8
Hz), 6.75-6.86 (m, 2 H), 7.01 (t, 1 H, J = 7.45
Hz), 7.14 (d, 1 H, J = 7.18 Hz),
7.28 (t, 1 H, J = 7.59
Hz). 13C NMR (50.3 MHz, CDCl3): δ = 21.9
(CH3), 26.9 (CH3,) 45.2 (CH), 51.7 (N-CH2),
107.8 (CH), 108.6 (CH), 109.2 (CH), 123.1 (CH), 124.0 (CH), 125.1
(CH), 125.6 (CH), 127.2 (quat-C), 127.3 (quat-C), 128.3 (quat-C),
129.0 (CH), 129.7 (CH), 138.7 (quat-C),
138.9 (quat-C), 144.9 (quat-C),
175.5 (quat-C). MS: m/z = 330 [M+].
Anal. Calcd for C22H22N2O: C, 79.97; H,
6.71; N, 8.48. Found: C, 79.74; H, 6.69; N, 8.51.
<A NAME="RD17202ST-14A">14a</A>
Bashford KE.
Cooper AL.
Kane PD.
Moody CJ.
Muthusamy S.
Swann E.
J. Chem. Soc., Perkin Trans. 1
2002,
1672
<A NAME="RD17202ST-14B">14b</A>
Bagley MC.
Buck RT.
Hind SL.
Moody CJ.
J.
Chem. Soc., Perkin Trans. 1
1998,
591
<A NAME="RD17202ST-14C">14c</A>
Bagley MC.
Moody CJ.
J.
Chem. Soc., Perkin Trans. 1
1998,
601
<A NAME="RD17202ST-15A">15a</A>
Hu W.
Timmons DJ.
Doyle MP.
Org. Lett.
2002,
4:
901
<A NAME="RD17202ST-15B">15b</A>
Davies HML.
Townsend RJ.
J.
Org. Chem.
2001,
66:
6595 ;
and references cited therein