An efficient synthesis of N-sbstituted-3-aryl-3-(2-hydroxy-4,4-dimethyl-6- oxocyclohex-1-enyl)propanamides by four-component reaction in aqueous medium

Article abstract of DOI:10.1002/cjoc.201180404

A mild and efficient synthesis of N-substituted-3-aryl-3-(2-hydroxy-4,4- dimethyl-6-oxocyclohex-1-enyl)propanamides via four-component reaction of an aldehyde, amine, Meldrum's acid and 5,5-dimethylcyclo-hexane-1,3-dione in the presence of benzyltriethyla

Full text of DOI:10.1002/cjoc.201180404

FULL PAPER
An Efficient Synthesis of N-Substituted-3-aryl-3-(2-hydroxy-4,4-
dimethyl-6-oxocyclohex-1-enyl)propanamides by
Four-component Reaction in Aqueous Medium
Dou, Guolana(窦国兰)
Zhong, Xiaoxinga(仲晓星)
Shi, Daqingb(史达清)
Wang, Deming*,a(王德明)
a School of Safety Engineering, China University of Mining & Technology, Xuzhou, Jiangsu 221116, China
b Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and
Materials Science, Soochow University, Suzhou, Jiangsu 215123, China
A
mild and efficient synthesis of N-substituted-3-aryl-3-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-
enyl)propanamides via four-component reaction of an aldehyde, amine, Meldrum’s acid and 5,5-dimethylcyclo-
hexane-1,3-dione in the presence of benzyltriethylammonium chloride (TEBAC) in aqueous medium is described.
This method has the advantages of accessible starting materials, good yields, mild reaction conditions and eco-
friendliness.
Keywords amide, four-component reaction, aqueous medium, synthetic method
Introduction
for the advantages concerning the avoidance of expen-
sive drying reactions, catalysts and solvents, but also for
some unique reactivity and selectivity.18 On the other
hand, organic reactions in water without using harmful
organic solvents is one of the current focuses especially
in the environmentally conscious society, because water
is abundant, nontoxic and environment-friendly when
compared with organic solvents used accordingly.
Multi-component reactions (MCRs), in which multi-
ple reactions are combined into the synthetic operation
have been used extensively to form carbon-carbon
bonds in the synthetic chemistry.19 Such reactions offer
a wide range of possibilities for the efficient construc-
tion of highly complex molecules in a single procedural
step, thus avoiding the complicated purification opera-
tions and allowing savings of both solvents and reagents.
In the past decade, there has been tremendous develop-
ment in three- and four-component reactions, and great
efforts continue to be made to develop new MCRs.20
As a continuation of our interest in green synthesis
and our previous work21 on multi-component reaction in
aqueous medium, herein we report a green, one-pot,
efficient synthesis of novel propanamide derivatives in
aqueous medium.
The amide bond plays an important role in the
elaboration and composition of biological and chemical
systems.1 Amides are traditionally synthesized by the
reaction of amines with activated carboxyl acid deriva-
tives.2 Recently there has been considerable interest in
the synthesis of amides. The Staudinger reaction,3 the
Beckmann rearrangement,4 Schmidt reaction,5 amino-
carbonylation of alkenes,6 haloarenes7 and alkynes,8
oxidative amidation of alhydes,9 hydrative amide syn-
thesis with alkynes,10 and the amidation of thio acids
with azides11 were used to synthesize amides. Jia et al.12
recently reported Samarium-mediated facile method for
the formation of amide bonds by the reaction of acyl
chlorides and amines. However, although these methods
have successfully led to a large library synthesis of am-
ides, many of them still suffer from drawbacks such as
using harmful organic synthesis, unsatisfactory yields
and occurrence of side reactions. Therefore, a method
with higher yield and environment-friendly manipula-
tion needs to be developed.
Science Breslow demonstrated hydrophobic efforts
could strongly enhance the rate of some organic reac-
tions and rediscovered the use of water as solvent in
organic synthesis in 1980s,13 there has been a growing
recognition that water has become an attractive medium
for many organic reactions, such as Diels-Alder reac-
tions,14 Claisen rearrangement reactions,15 Reformatsky
reactions16 and Pinacol-coupling reactions,17 not only
Results and discussion
When the four-component of aromatic aldehyde (1),
Meldrum’s acid (2), 5,5-dimethylcyclohexane-1,3-dione
(3) and amines (4) were treated in water in the presence
*
E-mail: wdmcumt@163.com
Received March 21, 2011; revised May 26, 2011; accepted June 15, 2011.
Project supported by the Fundamental Research Funds for the Central Universities (No. 2010QNB03) and the Priority Academic Program Develop-
ment of Jiangsu Higher Education Institutions.
2368
© 2011 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2011, 29, 2368— 2372

Synthesis of N-Substituted-3-aryl-3-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)propanamides
of TEBAC at 90 ℃ for 8—20 h, the desired product,
N-substituted-3-aryl-3-(2-hydroxy-4,4-dimethyl-6-oxo-
cyclohex-1-enyl)propanamides (5) were obtained
(Scheme 1).
Meldrum’s acid 2 afforded intermediate A. The Michael
addition of A with 5,5-dimethylcyclohexane-1,3-dione
(3) would then furnish the intermediate product B,
which subsequently underwent intramolecular cycliza-
tion and then released acetone and carbon dioxide to
give intermediate product C. The intermediate product
C was then attacked by amine 4 to give the product 5.
Scheme 1
Scheme 2 Possible mechanism for the formation of product 5
A range of novel valuable structures of 5 were
synthesized in good to excellent yields by simply
four-component reaction in aqueous media. The results
are summarized in Table 1.
Table 1 Synthesis of compounds 5 in aqueous media
Entry Product
Ar
R
Time/h Yield/%
1
5a 4-ClC6H4
4-CH3C6H4
4-CH3C6H4
4-CH3C6H4
8
95
97
97
93
92
98
97
96
95
95
94
2
5b 4-CH3C6H4
5c 4-CH3OC6H4
5d 4-CH3C6H4
5e 4-BrC6H4
5f 4-ClC6H4
12
20
In summary, a series of N-substituted-3-aryl-3-(2-
hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)propan-
amides were synthesized via four-component reaction of
aldehyde, amine, Meldrum’s acid and 5,5-dimethyl-
cyclohexane-1,3-dione in the presence of TEBAC in
aqueous medium. This protocol has the advantages of
accessible starting materials, high yield, mild reaction
condensations and eco-friendliness.
3
4
4-CH3OC6H4 15
4-CH3OC6H4 17
5
6
C6H5
C6H5
20
12
12
10
20
20
7
5g 4-CH3C6H4
8
5h 3,4-(CH3)2C6H3 C6H5
5i 3,4-(CH3O)2C6H3 C6H5
9
Experimental
10
11
5j 4-ClC6H4
3-ClC6H4
3-ClC6H4
Commercial solvents and reagents were used as re-
ceived. IR spectra were obtained on a Tensor 27 spec-
5k 4-CH3OC6H4
1
trophotometer. H NMR spectra were recorded using
As shown in Table 1, we were pleased to find that
Bruker DPX-400 MHz instrument, at 293 K unless oth-
erwise noted, with residue peaks of the solvents
DMSO-d6 (δ＝2.50) used for reference. HRMS were
obtained on a microma GCT-TOF instrument.
the method was applicable to a broad substrate scope on
both substituted aldehydes and amines. It can be seen
that this protocol can be applied to weak electron-
withdrawing groups (such as halide groups) or elec-
tron-donating groups (such as alkyl groups), which
highlighted the wide scope of this reaction. So we con-
cluded that no obvious effects from the electronic or
nature of the aromatic ring substrates were observed in
the above reactions.
Typical procedure for the synthesis of propanamides
5 in aqueous media
A mixture of the aldehyde 1 (2 mmol), Meldrum’s
acid 2 (2 mmol), 5,5-dimethylcyclohexane-1,3-dione 3
(2 mmol), amine 4 (2 mmol) and TEBAC (0.1 g) in wa-
ter (10 mL) was stirred for 8—20 h at 90 ℃, then
cooled to room temperature. The crystalline powder
formed was collected by filtration, washed with water
and recrystallized from ethanol to give pure 5.
1
All the products were characterized by H NMR, IR
and HRMS spectra.
Although the mechanism of the reaction has not yet
been established, a possible explanation is proposed in
Scheme 2.
3-(4-Chlorophenyl)-3-(2-hydroxy-4,4-dimethyl-6-
The reaction might proceed via sequential conden-
sation, addition, cyclization, and elimination. First, a
Knoevenagel condensation between aldehydes 1 and
oxocyclohex-1-enyl)-N-p-tolylpropanamide
(5a)
1
m.p. 239—240 ℃; H NMR (DMSO-d6, 400 MHz) δ:
0.93 (s, 6H, 2×CH3), 2.35—2.20 (m, 7H, CH3＋2×
2369
Chin. J. Chem. 2011, 29, 2368— 2372
© 2011 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
www.cjc.wiley-vch.de

Dou et al.
FULL PAPER
－
1
CH2), 2.80 (dd, J＝6.8, 14.8 Hz, 1H, CH), 3.24 (dd, J＝
8.4, 14.8 Hz, 1H, CH), 4.73 (t, J＝7.6 Hz, 1H, CH),
7.04 (d, J＝8.0 Hz, 2H, ArH), 7.29—7.24 (m, 4H, ArH),
7.41 (d, J＝8.4 Hz, 2H, ArH), 9.80 (s, 1H, NH), 10.64
(s, 1H, OH); IR (KBr) ν: 3293, 3125, 3068, 1668, 1602,
1559, 1514, 1491, 1449, 1377, 1309, 1281, 1249, 1092,
921, 816, 780, 757, 723 cm － 1. HRMS calcd for
C24H2635ClNO3 434.1499 (M＋Na), found 434.1505.
3-(2-Hydroxy-4,4-dimethyl-6-oxocyclohex-1-
enyl)-N,3-di(p-tolyl)propanamide (5b) m.p. 221—
921, 83, 756, 718 cm
.
HRMS calcd for
C24H2679BrNO4 472.1123 (M＋H), found 472.1118.
3-(4-Chlorophenyl)-3-(2-hydroxy-4,4-dimethyl-6-
oxocyclohex-1-enyl)-N-phenylpropanamide
(5f)
m.p. 215—217 ℃ (Lit.22 208—210 ℃); H NMR
(DMSO-d6, 400 MHz) δ: 0.93 (s, 6H, 2×CH3), 2.30—
2.05 (m, 4H, 2×CH2), 2.82 (dd, J＝6.8, 14.8 Hz, 1H,
CH), 3.27 (dd, J＝8.8, 14.8 Hz, 1H, CH), 4.74 (t, J＝7.6
Hz, 1H, CH), 6.99 (t, J＝7.2 Hz, 1H, ArH), 7.30—7.22
(m, 6H, ArH), 7.53 (d, J＝8.4 Hz, 2H, ArH), 9.91 (s, 1H,
NH), 10.67 (s, 1H, OH); IR (KBr) ν: 3289, 3080, 1654,
1
223 ℃ (Lit.22 218—220 ℃); H NMR (DMSO-d6,
1
400 MHz) δ: 0.92 (s, 6H, 2×CH3), 2.35—2.00 (m, 10H,
2×CH3＋2×CH2), 2.81 (dd, J＝7.2, 14.8 Hz, 1H, CH),
3.21 (dd, J＝8.4, 14.8 Hz, 1H, CH), 4.70 (t, J＝7.6 Hz,
1H, CH), 6.98 (d, J＝8.0 Hz, 2H, ArH), 7.04 (d, J＝8.0
Hz, 2H, ArH), 7.15 (d, J＝8.0 Hz, 2H, ArH), 7.42 (d,
J＝8.0 Hz, 2H, ArH), 9.77 (s, 1H, NH), 10.48 (s, 1H,
OH); IR (KBr) ν: 3297, 3195, 3029, 1670, 1618, 1601,
1550, 1513, 1446, 1379, 1262, 1249, 1046, 983, 936,
816, 752, 718 cm－ 1. HRMS calcd for C25H29NO3
392.2226 (M＋H), found 392.2230.
1602, 1550, 1491, 1444, 1377, 1309, 1254, 1148, 1051,
－
821, 755, 727, 691 cm 1. HRMS calcd for
C23H2435ClNO3 420.1343 (M＋Na), found 420.1372.
3-(2-Hydroxy-4,4-dimethyl-6-oxocyclohex-1-
enyl)-N-phenyl-3-p-tolylpropanamide (5g) m.p. 237
—239 ℃ (Lit.22 233—235 ℃); H NMR (DMSO-d6,
1
400 MHz) δ: 0.92 (s, 6H, 2×CH3), 2.05 (s, 2H, CH2),
2.20 (s, 3H, CH3), 2.28 (s, 2H, CH2), 2.82 (dd, J＝6.8,
14.8 Hz, 1H, CH), 3.24 (dd, J＝8.8, 14.8 Hz, 1H, CH),
4.71 (t, J＝7.6 Hz, 1H, CH), 7.00—6.97 (m, 3H, ArH),
7.16 (d, J＝8.0 Hz, 2H, ArH), 7.24 (t, J＝7.6 Hz, 2H,
ArH), 7.54 (d, J＝8.0 Hz, 2H, ArH), 9.87 (s, 1H, NH),
10.50 (s, 1H, OH); IR (KBr) ν: 3297, 3197, 3049, 1654,
1602, 1551, 1514, 1498, 1488, 1442, 1376, 1254, 1176,
3-(2-Hydroxy-4,4-dimethyl-6-oxocyclohex-1-
enyl)-3–(4-methoxyphenyl)-N-p-tolylpropanamide
1
(5c) m.p. 204—206 ℃; H NMR (DMSO-d6, 400
MHz) δ: 0.92 (s, 6H, 2×CH3), 2.04 (s, 2H, CH2), 2.22
(s, 3H, CH3), 2.33 (s, 2H, CH2), 2.81 (dd, J＝6.8, 14.8
Hz, 1H, CH), 3.19 (dd, J＝8.4, 14.8 Hz, 1H, CH), 3.69
(s, 3H, CH3O), 4.68 (t, J＝7.6 Hz, 1H, CH), 6.75 (d, J＝
8.4 Hz, 2H, ArH), 7.04 (d, J＝8.4 Hz, 2H, ArH), 7.19 (d,
J＝8.4 Hz, 2H, ArH), 7.42 (d, J＝8.4 Hz, 2H, ArH),
9.76 (s, 1H, NH), 10.48 (s, 1H, OH); IR (KBr) ν: 3297,
3196, 3058, 1668, 1615, 1560, 1513, 1448, 1379, 1247,
1150, 829, 815 cm－ 1. HRMS calcd for C25H29NO4
430.1995 (M＋Na), found 430.2008.
－
1
1116, 1095, 972, 795, 758, 723, 691 cm . HRMS calcd
for C24H27NO3 400.1889 (M＋Na), found 400.1946.
3-(2-Hydroxy-4,4-dimethyl-6-oxocyclohex-1-
enyl)-3-(3,4-dimethylphenyl)-N–phenylpropanamide
1
(5h) m.p. 218—220 ℃; H NMR (DMSO-d6, 400
MHz) δ: 0.93 (s, 6H, 2×CH3), 2.35—2.05 (m, 10H, 2
×CH3＋2×CH2), 2.83 (dd, J＝6.8, 14.8 Hz, 1H, CH),
3.22 (dd, J＝8.4, 14.8 Hz, 1H, CH), 4.89 (t, J＝7.6 Hz,
1H, CH), 6.92—6.99 (m, 3H, ArH), 7.04 (s, 1H, ArH),
7.24 (t, J＝7.6 Hz, 2H, ArH), 7.56 (d, J＝8.0 Hz, 2H,
ArH), 9.86 (s, 1H, NH), 10.47 (s, 1H, OH); IR (KBr) ν:
3279, 3139, 3053, 1641, 1597, 1558, 1499, 1485, 1456,
3-(2-Hydroxy-4,4-dimethyl-6-oxocyclohex-1-
enyl)-N–(4-methoxyphenyl)-3-p-tolylpropanamide
1
(5d) m.p. 227—229 ℃; H NMR (DMSO-d6, 400
－
1
MHz) δ: 0.93 (s, 6H, 2×CH3), 2.05 (s, 2H, CH2), 2.21
(s, 3H, CH3), 2.35 (s, 2H, CH2), 2.79 (dd, J＝7.2, 14.8
Hz, 1H, CH), 3.19 (dd, J＝8.4, 14.8 Hz, 1H, CH), 3.69
(s, 3H, CH3O), 4.70 (t, J＝7.6 Hz, 1H, CH), 6.82 (d, J＝
8.8 Hz, 2H, ArH), 6.98 (d, J＝8.0 Hz, 2H, ArH), 7.15 (d,
J＝8.0 Hz, 2H, ArH), 7.44 (d, J＝8.8 Hz, 2H, ArH),
9.71 (s, 1H, NH), 10.48 (s, 1H, OH); IR (KBr) ν: 3202,
3139, 3082, 1664, 1615, 1558, 1512, 1465, 1379, 1246,
1376, 1249, 1096, 971, 927, 891, 814, 749, 718 cm .
HRMS calcd for C25H29NO3 414.2045 (M＋Na), found
414.2107.
3-(2-Hydroxy-4,4-dimethyl-6-oxocyclohex-1-
enyl)-3-(3,4-dimethoxyphenyl)-N–phenylpropan-
1
amide (5i) m.p. 223—224 ℃; H NMR (DMSO-d6,
400 MHz) δ: 0.94 (s, 6H, 2×CH3), 2.07 (s, 2H, CH2),
2.34 (s, 2H, CH2), 2.83 (dd, J＝6.8, 14.8 Hz, 1H, CH),
3.23 (dd, J＝8.8, 14.8 Hz, 1H, CH), 3.66 (s, 3H, CH3O),
3.67 (s, 3H, CH3O), 4.70 (t, J＝8.0 Hz, 1H, CH), 6.77 (s,
2H, ArH), 6.91 (s, 1H, ArH), 6.98 (t, J＝7.6 Hz, 1H,
ArH), 7.24 (t, J＝8.0 Hz, 2H, ArH), 7.55 (d, J＝8.0 Hz,
2H, ArH), 9.88 (s, 1H, NH), 10.52 (s, 1H, OH); IR (KBr)
ν: 3275, 3136, 3089, 1640, 1612, 1555, 1517, 1501,
1489, 1465, 1455, 1381, 1269, 1229, 1048, 1025, 970,
850, 766, 701 cm－ 1. HRMS calcd for C25H29NO5
446.1944 (M＋Na), found 446.1972.
－
1
1108, 923, 824, 792, 750, 717 cm . HRMS calcd for
C25H29NO4 430.1995 (M＋Na), found 430.2037.
3-(4-Bromophenyl)-3-(2-hydroxy-4,4-dimethyl-6-
oxocyclohex-1-enyl)-N–(4-methoxyphenyl)propan-
1
amide (5e) m.p. 217—219 ℃; H NMR (DMSO-d6,
400 MHz) δ: 1.07 (s, 6H, 2×CH3), 2.15 (s, 2H, CH2),
2.35 (s, 2H, CH2), 2.92 (dd, J＝6.8, 14.8 Hz, 1H, CH),
3.37 (dd, J＝8.8, 14.8 Hz, 1H, CH), 3.84 (s, 3H, CH3O),
4.86 (t, J＝7.6 Hz, 1H, CH), 6.97 (d, J＝8.8 Hz, 2H,
ArH), 7.37 (d, J＝8.4 Hz, 2H, ArH), 7.53 (d, J＝8.0 Hz,
2H, ArH), 7.58 (d, J＝8.8 Hz, 2H, ArH), 9.91 (s, 1H,
NH), 10.80 (s, 1H, OH); IR (KBr) ν: 3298, 3140, 3078,
1664, 1638, 1615, 1557, 1511, 1463, 1376, 1249, 1108,
N-(3-Chlorophenyl)-3-(4-chlorophenyl)-3-(2-
hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl) propan-
1
amide (5j) m.p. 237—238 ℃; H NMR (DMSO-d6,
400 MHz) δ: 0.92 (s, 6H, 2×CH3), 2.04 (s, 2H, CH2),
2370
www.cjc.wiley-vch.de
© 2011 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2011, 29, 2368— 2372

Synthesis of N-Substituted-3-aryl-3-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)propanamides
(b) Uenoyama, Y.; Fukuyama, T.; Nobuta, O.; Matsubara,
2.31 (s, 2H, CH2), 2.88 (dd, J＝6.8, 14.8 Hz, 1H, CH),
3.26 (dd, J＝8.4, 14.8 Hz, 1H, CH), 4.73 (t, J＝7.6 Hz,
1H, CH), 7.05 (d, J＝8.0 Hz, 1H, ArH), 7.29—7.25 (m,
5H, ArH), 7.38 (d, J＝8.0 Hz, 1H, ArH), 7.77 (s, 1H,
ArH), 10.11 (s, 1H, NH), 10.69 (s, 1H, OH); IR (KBr) ν:
3279, 3241, 3071, 1656, 1608, 1536, 1492, 1477, 1374,
H.; Ryu, I. Angew. Chem., Int. Ed. 2005, 44, 1075.
(c) Knapton, D. J.; Meyer, T. Y. Org. Lett. 2004, 6, 687.
(a) Naota, T.; Murahashi, S. I. Synlett 1991, 693.
(b) Tillack, A.; Rudloff, I.; Beller, M. Eur. J. Org. Chem.
2001, 523.
9
－
1
(c) Chang, J. W. W.; Chan, P. W. H. Angew. Chem., Int. Ed.
2008, 47, 1138.
1276, 1251, 1095, 960, 876, 849, 780, 729, 691 cm .
HRMS calcd for C23H2335Cl2NO3 454.0953 (M＋Na),
found 454.0972.
(d) Yoo, W. J.; Li, C. J. J. Am. Chem. Soc. 2006, 128,
13064.
N-(3-Chlorophenyl)-3-(2-hydroxy-4,4-dimethyl-
6-oxocyclohex-1-enyl)-3-(4-methoxyphenyl)propan-
10 Cho, S.; Yoo, E.; Bae, I.; Chang, S. J. Am. Chem. Soc. 2005,
127, 16046.
1
amide (5k) m.p. 227—229 ℃; H NMR (DMSO-d6,
11 (a) Zhang, X.; Li, F.; Lu, X. W.; Liu, C. F. Bioconjugate
Chem. 2009, 20, 197.
400 MHz) δ: 0.92 (s, 6H, 2×CH3), 2.30—2.02 (m, 4H,
2×CH2), 2.89 (dd, J＝7.6, 14.8 Hz, 1H, CH), 3.21 (dd,
J＝8.8, 14.8 Hz, 1H, CH), 3.68 (s, 3H, CH3O), 4.69 (t,
J＝8.0 Hz, 1H, CH), 6.76 (d, J＝8.4 Hz, 2H, ArH), 7.04
(d, J＝8.0 Hz, 1H, ArH), 7.19 (d, J＝8.4 Hz, 2H, ArH),
7.28 (t, J＝8.0 Hz, 1H, ArH), 7.40 (d, J＝8.4 Hz, 1H,
ArH), 7.79 (s, 1H, ArH), 10.08 (s, 1H, NH), 10.52 (s,
1H, OH); IR (KBr) ν: 3242, 3183, 3066, 1656, 1583,
1544, 1511, 1477, 1453, 1425, 1370, 1265, 1185, 1027,
970, 881, 787, 733, 706 cm － 1. HRMS calcd for
C24H2635ClNO4 450.1448 (M＋Na), 450.1445.
(b) Kolakowski, R. V.; Shangguan, N.; Sauers, R. R.;
Williams, L. J. J. Am. Chem. Soc. 2006, 128, 5695.
12 Shi, F.; Li, J.; Li, C.; Jia, X. S. Tetrahedron Lett. 2010, 51,
6049.
13 (a) Breslow, R.; Rideout, D. C. J. Am. Chem. Soc. 1980, 102,
7816.
(b) Breslow, R. Acc. Chem. Res. 1991, 24, 159.
14 Breslow, R.; Maitra, U. Tetrahedron Lett. 1984, 25, 1239.
15 (a) Ponaras, A. A. J. Org. Chem. 1983, 48, 3866.
(b) Coates, R. M.; Rogers, B. D.; Hobbs, S. J.; Peck, D. R.;
Curran, D. P. J. Am. Chem. Soc. 1987, 109, 1160.
16 (a) Mattes, H.; Benezra, C. Tetrahedron Lett. 1985, 26,
5697.
References
1
2
3
(a) Bode, J. W. Curr. Opin. Drug Discov. Devel. 2006, 9,
765.
(b) Humphrey, J. M.; Chamberlin, A. R. Chem. Rev. 1997,
97, 2243.
(c) Cupido, T.; Tulla-Puche, J.; Spengler, J.; Albericio, F.
Curr. Opin. Drug Discov. Devel. 2007, 10, 768.
(a) Larock, R. C. In Comprehensive Organic
Transformations, VCH, New York, 1999.
(b) Valeur, E.; Bradley, M. Chem. Soc. Rev. 2009, 38, 606.
(c) Han, S. Y.; Kim, Y. A. Tetrahedron 2004, 60, 2447.
(d) Montalbetti, C. A. G. N.; Falque, V. Tetrahedron 2005,
61, 10827.
(b) Zhou, J. Y.; Lu, G. D.; Wu, S. H. Synth. Commun. 1992,
22, 481.
17 Delair, P.; Luche, J. L. J. Chem. Soc., Chem. Commun. 1989,
398.
18 (a) Brelow, R.; Maitra, U.; Rideout, D. C. Tetrahedron Lett.
1983, 24, 1901.
(b) Tan, X. H.; Hou, Y. Q.; Huang, C.; Liu, L.; Guo, Q. X.
Tetrahedron 2004, 60, 6129.
(c) Copley, S. D.; Khowles, J. R. J. Am. Chem. Soc. 1987,
109, 5008.
(d) Khosropour, A. R.; Khodaei, M. M.; Kookhazadeh, M.
Tetrahedron Lett. 2004, 45, 1725.
(a) Pianowski, Z.; Gorska, K.; Oswald, L.; Merten, C. A.;
Winssinger, N. J. Am. Chem. Soc. 2009, 131, 6492.
(b) Damkaci, F.; Deshong, P. J. Am. Chem. Soc. 2003, 125,
4408.
19 (a) Bigenayme, H.; Hulme, C.; Oddon, G.; Schmitt, P.
Chem. Eur. J. 2000, 6, 3321.
(b) Tietze, L. F.; Modi, A. Med. Res. Rev. 2000, 20, 304.
(c) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39,
3168.
(c) Saxon, E.; Bertozzi, C. R. Science 2000, 287, 2007.
(a) Hashimoto, M.; Obora, Y.; Sakaguchi, S.; Ishii, Y. J.
Org. Chem. 2008, 73, 2894.
(b) Owston, N. A.; Parker, A. J.; Williams, J. M. J. Org. Lett.
2007, 9, 3599.
(a) Lang, S.; Murphy, J. A. Chem. Soc. Rev. 2006, 35, 146
(b) Ribelin, T.; Katz, C. E.; English, D. G.; Smith, S.;
Manukyan, A. K.; Day, V. W.; Neuenswander, B.; Poutsma,
J. L.; Aube, J. Angew. Chem., Int. Ed. 2008, 47, 6233.
Beller, M.; Cornils, B.; Frohning, C. D.; Kohlpaintner, C. W.
J. Mol. Catal. A: Chem. 1995, 104, 17.
(a) Nanayakkara, P.; Alper, H. Chem. Commun. 2003, 2384.
(b) Martinelli, J. R.; Clark, T. P.; Watson, D. A.; Munday, R.
H.; Buchwald, S. L. Angew. Chem., Int. Ed. 2007, 46, 8460.
(a) Park, J. H.; Kim, S. Y.; Kim, S. M.; Chung, Y. K. Org.
Lett. 2007, 9, 2465.
4
5
(d) Zhu, J. Eur. J. Org. Chem. 2003, 1133.
(e) Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471.
(f) Nair, V.; Rajsh, C.; Vinod, A. V.; Bindu, S.; Sreekanth,
A. R.; Mathen, J. S.; Balagopal, L. Acc. Chem. Res. 2003,
36, 899.
(g) Simon, C.; Constantieux, T.; Rodriguez, J. Eur. J. Org.
Chem. 2004, 4957.
6
7
(h) Ramon, D. J.; Yus, M. Angew. Chem., Int. Ed. 2005, 44,
1602.
20 (a) Nair, V.; Vinod, A. U.; Rajesh, C. J. Org. Chem. 2001,
66, 4427.
(b) List, B.; Castello, C. Synlett 2001, 1687.
(c) Shestopalov, A. M.; Emeliyanova, Y. M.; Shestiopolov,
8
Chin. J. Chem. 2011, 29, 2368— 2372
© 2011 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
www.cjc.wiley-vch.de
2371

Dou et al.
FULL PAPER
A. A.; Rodinovskaya, L. A.; Niazimbetova, Z. I.; Evans, D.
H. Org. Lett. 2002, 4, 423.
(d) Bertozzi, F.; Gustafsson, M.; Olsson, R. Org. Lett. 2002,
4, 3147.
(e) Yuan, Y.; Li, X.; Ding, K. Org. Lett. 2002, 4, 3309.
(f) Cheng, J. F.; Chen, M.; Arthenius, T.; Nadzen, A. Tet-
rahedron Lett. 2002, 43, 6293.
2003, 5, 1205.
21 (a) Shi, D. Q.; Niu, L. H.; Shi, J. W.; Wang, X. S.; Ji, S. J. J.
Heterocycl. Chem. 2007, 44, 1083.
(b) Shi, D. Q.; Yao, H.; Shi, J. W. Synth. Commun. 2008, 38,
1662.
(c) Shi, D. Q.; Niu, L. H.; Yao, H.; Jiang, H. J. Heterocycl.
Chem. 2009, 46, 237.
(g) Huma, H. Z. S.; Halder, R.; Kalra, S. S.; Das, J.; Iqbal, J.
Tetrahedron Lett. 2002, 43, 6485.
(d) Shi, D. Q.; Shi, J. W.; Yao, H. Synth. Commun. 2009, 39,
664.
(h) Bora, U.; Saikia, A.; Boruah, R. C. Org. Lett. 2003, 5,
435.
(i) Dallinger, D.; Gorobets, N. Y.; Kappe, C. O. Org. Lett.
(e) Shi, D. Q.; Yao, H. Synth. Commun. 2009, 39, 2481.
22 Wang, X. S.; Shi, D. Q.; Tu, S. J. Chin. J. Org. Chem. 2002,
22, 909.
(E1103211 Cheng, F.)
2372
www.cjc.wiley-vch.de
© 2011 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2011, 29, 2368— 2372