Isoindolone synthesis via palladium-catalysed intramolecular amination of benzylic C-H bonds

Article abstract of DOI:10.3184/174751913X13801883437178

A new method for the construction of isoindolones is presented in this paper. Four 7-methyl-2-(8-quinolinyl)-2,3-dihydro-1Hisoindol-1-ones were synthesised from 2,6-dimethyl -N-(8-quinolinyl)benzamides via intramolecular direct amination of benzylic C-H bonds. This approach provides a convenient method affording structurally new isoindolones for medicinal chemistry research.

Full text of DOI:10.3184/174751913X13801883437178

606 RESEARCH PAPER
OCTOBER, 606–610
JOURNAL OF CHEMICAL RESEARCH 2013
Isoindolone synthesis via palladium-catalysed intramolecular amination of
benzylic C–H bonds
Ming Zhanga*
aCollege of Chemistry and Key Laboratory of Functional Small Organic Molecules, Ministry of Education, Jiangxi Normal University
(Yaohu campus), 99 Ziyangdadao, Nanchang, Jiangxi 330022, P.R. China.
A new method for the construction of isoindolones is presented in this paper. Four 7-methyl-2-(8-quinolinyl)-2,3-dihydro-1H-
isoindol-1-ones were synthesised from 2,6-dimethyl -N-(8-quinolinyl)benzamides via intramolecular direct amination of benzylic
C–H bonds. This approach provides a convenient method affording structurally new isoindolones for medicinal chemistry
research.
Keywords: amination, coupling, lactam, palladium, cyclisation
Construction of heterocyclic scaffolds via sp3 C–H
functionalisation has witnessed great progress in recent
years,1–4 this strategy provides straightforward and efficient
methods for synthesis of various heterocyclic compounds.
The direct coupling of a sp3 C–H bond with a heteroatom is
a challenge in this research area. In 2006, pioneering work in
this field was reported by Chang’s group.5 Formation of aryl
lactones was achieved by coupling of a sp3 C–H bond and a
pendant oxygen function.5,6 4H-3,1-Benzoxazines and oxazoles
were also synthesised via coupling of a sp3 C–H bond with the
oxygen atom of an amide group.7,8 In 2009, Glorius’s group
reported coupling of a sp3 C–H bond with a nitrogen atom
leading to indolines from anilines.9 In 2011, a picolinamide
directed coupling of a sp3 C–H bond with a N–H bond was
used to form four-, five- and six-membered heterocycles.10,11
An N-substituted isoindolone is the intermediate of a mGluR2
positive allosteric modulator of an indicator of schizophrenia.
In the literature,12 three steps were needed to construct the
isoindolone scaffold from 4-bromo-2,6-dimethylbenzoic
acid in 33% overall yield. We now report that the isoindolone
scaffold can be constructed in a two-step procedure from the
same starting material in 75% overall yield (Scheme 1). This
approach will provide structurally diverse compounds for
medicinal chemistry research. Here we describe the synthesis
of isoindolones via intramolecular coupling of a benzylic C–H
bond with an amide N–H bond.
Results and discussion
It was found that N-(8-quinolinyl)-2,4,6-trimethylbenzamide
1a could be cyclised to afford 5,7-dimethyl-2-(8-quinolinyl)-
2,3-dihydro-1H-isoindol-1-one 2a in 73% yield via benzylic
C–H-amide N–H coupling (Table 1), using Pd(OAc)2 (5 mol%)
as a catalyst and PhI(OAc)2 (2.5 equiv.) as an oxidant. An acidic
additive is essential in this cyclisation, and of those tested, HOAc
gave the best result.
With the optimised reaction conditions in hand, the scope
of substrate variation was explored (Table 2). It was observed
that N-(8-quinolinyl)- and 2,6-dimethylbenzoyl were essential
moieties in the substrates for cyclisation and gave the products in
Table 1 Optimisation of the reaction conditions for the couplinga
Pd(OAc)
oxidant
additive
2
O
O
N
N
H
solvent, N
2
N
N
2a
1a
Pd(OAc) /
mol% 2
Additive
Reaction
time/h
Entry
Oxidant (equiv.)
Solvent
T/°C
Yield/%b
/5 equiv.
–
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
10
10
10
10
10
10
10
10
10
10
10
5
AgOAc (3)
PhI(OAc)2 (2.5)
Cu(OAc)2 (3)
Selectfluor (3)
Na2S2O8 (6)
Na2S2O8 (3)
Na2S2O8 (3)
Na2S2O8 (3)
Na2S2O8 (3)
PhI(OAc)2 (2.5)
PhI(OAc)2 (2.5)
PhI(OAc)2 (2.5)
PhI(OAc)2 (2.5)
PhI(OAc)2 (2.5)
PhI(OAc)2 (2.5)
PhI(OAc)2 (2.5)
DCE
DCE
DCE
DCE
DCE
DCE
DCE
DCE
DCE
70
70
70
70
70
70
70
70
70
24
24
24
24
24
24
24
24
24
24
72
24
24
24
24
24
0
0
0
0
0
0
0
0
0
–
–
–
–
HOAc
TFA
CF3SO3H
K2CO3 (3)
HOAc
HOAc
TFA
HOAc
tBuCOOH
CF3SO3H
HOAc
Mesitylene
DCE
140
70
31
26
trace
43
34
0
Toluene
Toluene
Toluene
Toluene
Mesitylene
100
100
100
100
120
5
5
5
5
73
aReaction conditions: 1a (0.29 mmol), Pd(OAc)2, oxidant, additive, solvent (2 mL), heat.
bIsolated yield.
* Correspondent. E-mail: zmchem@163.com
57–88% yield. The substrates 1c and 1d containing fluorine and
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JOURNAL OF CHEMICAL RESEARCH 2013 607
1) Literature procedure12
:
H2N
O
i) NBS, (PhC(O)O)2
ii) NaBH4
OCF3
COOH
O
59%
AlMe3, 73%
Br
Br
OCF3
O
i) Ms2O
ii)LDA or NaOPt
O
N
N
H
77%
Br
OCF3
OH
Br
O
overall yield: 33%
2) This work:
i) SOCl2
ii) 8-aminoquinoline
COOH
N
H
92%
N
Br
Br
1c
O
N
Pd(OAc)2
PhI(OAc)2
HOAc
Br
81%
N
2c
overall yield: 75%
Scheme 1 Two routes to isoindolones.
Scheme 2 A possible mechanism.
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608 JOURNAL OF CHEMICAL RESEARCH 2013
Table 2 Cyclisation studiesa
Entry
Substrate
Product
Yield/%
73
O
O
N
H
N
1
N
N
2a
1a
O
O
N
N
H
2
3
4
57
81
88
N
N
1b
2b
O
O
N
N
H
Br
N
N
Br
1c
2c
O
O
N
N
H
F
N
N
F
1d
2d
AcO
O
O
O
+
N
H
N
N
5
6
10+ 14
H
H
N
N
N
OAc
OAc
2e-1
1e
2e-2
O
O
CH
3
N
H
0
CH
N
3
1f
aReaction conditions: 1 (0.29 mmol), Pd(OAc)2 (5 mol%), PhI(OAc)2 (2.5 equiv.), HOAc (5 equiv), Mesitylene (2 mL),
120 °C, 24 h.
spectrometer. High-resolution mass spectra (HRMS) were obtained on
bromine substituents gave higher yields (81 and 88% respectively)
a Waters Micromass GCT Premier spectrometer.
than those from 1a and 1b. There are not obvious electronic
effects on the cyclisation yields. When 2-methyl-N-(8-quinolinyl)
benzamide 1e was tested both mono- and di-acetoxylated
products were isolated, and no cyclisation product was obtained.
The substrate 1f without an N-(8-quinolinyl) function was tested
under the reaction conditions, but no cyclisation occurred.
A possible mechanism involves2,8,12,13 benzylic C–H activation
of 1a–d, directed by the bidentate 8-aminoquinoline system, to
produce intermediate A, then reductive elimination gives the
product 2a–d and Pd(0). Oxidation of Pd(0) to Pd(II) completes
the Pd(II)–Pd(0) catalytic cycle. A Pd(II)–Pd(IV) catalytic cycle
is also possible. Thus, intermediate A is oxidised to the Pd(IV)
species B, then reductive elimination gives the product 2a–d and
Pd(II) so completing the catalytic cycle (Scheme 2).
In summary, a method for the construction of isoindolones
from 2,6-dimethyl-N-(8-quinolinyl)benzamides is described.
This approach involves the directed amination of benzylic C–H
bonds via the bidentate 8-aminoquinoline system. Four desired
compounds were synthesised in 57–88% yields. The present
synthetic route for the construction of isoindolones is new,
straightforward and helpful for medicinal chemistry research.
N-(8-Quinolinyl)benzamides (1a–e); general procedure
A solution of 8-aminoquinoline (0.3950 g, 2.74 mmol) and Et3N
(0.42 mL, 3 mmol) in CH2Cl2 (5 mL) was cooled to 0 °C, then an acyl
chloride (2.74 mmol) was added (the acyl chloride was prepared by
reaction of the appropriate carboxylic acid with SOCl2). After addition,
the reaction mixture was warmed to room temperature and stirred
for 24 h. The reaction mixture was washed with water (1 mL), brine
(1.5 mL×ꢀ3), and dried over Na2SO4. The solvent was removed and the
product was obtained by recrystallisation or flash chromatography.
N-(8-Quinolinyl)-2,4,6-trimethylbenzamide (1a): Yield: 0.66 g (87%);
1
pale brown crystals; m.p. 142–144 °C. H NMR (400 MHz, CDCl3):
δ 2.34 (s, 3H, Me), 2.40 (s, 6H, 2Me), 6.94 (s, 2H, ArH), 7.44–7.47 (q,
J=4 Hz, 1H, ArH), 7.56–7.63 (m, 2H, ArH), 8.19 (app. d, Japp. =8.4 Hz,
1H, ArH), 8.74 (t, J=2.4 Hz, 1H, ArH), 8.99 (app. d, Japp. =7.6 Hz, 1H,
ArH), 9.95 (s, 1H, NH). 13C NMR (100 MHz, CDCl3): δ=19.44, 21.18,
116.81, 121.64, 121.86, 127.48, 128.01, 128.42, 134.43, 134.53, 135.33,
136.49, 138.38, 138.77, 148.16, 169.17. HRMS (EI): m/z [M+] calcd for
C19H18N2O: 290.1419; found: 290.1422.
2,6-Dimethyl-N-(8-quinolinyl)benzamide (1b): Yield: 0.67 g (89%);
colourless crystals; m.p. 153–159 °C. 1H NMR (400 MHz, CDCl3):
δ 2.44 (s, 6H, 2Me), 7.11 (app. d, Japp. =7.6 Hz, 2H, ArH), 7.23 (app. d,
Experimental
Japp. =7.6 Hz, 1H, ArH), 7.45 (dd, J=4.4, 10 Hz, 1H, ArH), 7.58–7.62 (m,
All reactions were performed under an atmosphere of nitrogen.
1H NMR and 13C NMR spectra were recorded on a Bruker Avance
400 spectrometer with TMS as the internal standard and CDCl3 as
solvent. 19F NMR spectra were determined on a Bruker Avance 500
spectrometer. MS were recorded on an Agilent Technologies 5973 N
2H, ArH), 8.18 (app. d, Japp. =8.4 Hz, 1H, ArH), 8.74 (app. d, Japp. =2.8 Hz,
1H, ArH), 8.98 (app. d, Japp. =7.2 Hz, 1H, ArH), 9.93 (s, 1H, NH). 13C
NMR (100 MHz, CDCl3): δ 19.46, 16.81, 121.67, 121.94, 127.44, 127.73,
128.05, 128.99, 134.46, 134.59, 136.35, 138.08, 138.59, 148.30, 168.89.
HRMS (EI): m/z [M+] calcd For C18H16N2O: 276.1263; found 276.1265.
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JOURNAL OF CHEMICAL RESEARCH 2013 609
4-Bromo-2,6-dimethyl-N-(8-quinolinyl)benzamide
(1c):
Yield:
7.83 (app. d, Japp. =8 Hz, 1H, ArH), 7.92 (app. d, Japp. =7.6 Hz, 1H, ArH),
8.22 (app. d, Japp. =8 Hz, 1H, ArH), 8.89 (t, J=2 Hz. 1H, ArH). 13C NMR
(100 MHz, CDCl3): δ 17.41, 53.21, 120.11, 121.35, 126.39, 127.39, 128.89,
129.49, 129.63, 129.86, 131.27, 135.78, 136.34, 138.38, 143.07, 144.51,
150.01, 169.63. HRMS (EI): m/z [M+] calcd for C18H14N2O: 274.1106;
found: 274.1105.
0.89 g (92%); colourless crystals; m.p. 155–156 °C. 1H NMR (400 MHz,
CDCl3): δ 2.41 (s, 6H, 2Me), 7.28 (s, 2H, ArH), 7.45–7.47 (m, 1H, ArH),
7.57–7.61 (m, 2H, ArH), 8.18 (app. d, Japp. =8 Hz, 1H, ArH), 8.74 (d,
J=2 Hz, 1H, ArH), 8.94 (app. d, Japp. =6.8 Hz, 1H, ArH), 9.90 (s, 1H, NH).
13C NMR (100 MHz, CDCl3): δ 19.28, 116.84, 121.74, 122.15, 122.87,
127.40, 128.04, 130.59, 134.19, 136.38, 136.82, 136.94, 138.53, 148.39,
167.85. HRMS (EI): m/z [M+] calcd for C18H1579BrN2O: 354.0368; found:
354.0366.
5-Bromo-7-methyl-2-(8-quinolinyl)-2,3-dihydro-1H-isoindol-1-one
1
(2c): Pale yellow solid; m.p. 245–246 °C. H NMR (400 MHz, CDCl3):
δ 2.76(s, 3H, Me), 5.21 (s, 2H, CH2), 7.42–7.45 (m, 2H, ArH), 7.49 (s,
1H, ArH), 7.63 (t, J=8 Hz, 1H, ArH), 7.83 (app. d, Japp. =8.4 Hz, 1H,
ArH), 7.90 (app. d, Japp. =7.2 Hz, 1H, ArH), 8.22 (m, 1H, ArH), 8.87 (m,
1H, ArH). 13C NMR (100 MHz, CDCl3): δ 17.16, 52.73, 121.44, 123.45,
125.85, 126.38, 127.60, 128.70, 128.84, 129.48, 132.95, 135.31, 136.38,
140.23, 144.35, 144.81, 150.07, 168.75. HRMS (EI): m/z [M+] calcd for
C18H1379BrN2O: 352.0211; found: 352.0214.
2,6-Dimethyl-4-fluoro-N-(8-quinolinyl)benzamide
(1d):
Yield:
0.73 g (91%); colourless crystals; m.p. 136–138 °C. 1H NMR (400 MHz,
CDCl3): δ 2.43 (s, 6H, 2Me), 6.81 (app. d, Japp =9.2 Hz, 2H, ArH), 7.46 (q,
J=4 Hz, 1H, ArH), 7.57–7.62 (m, 2H, ArH), 8.19 (app. d, Japp =8.4 Hz, 1H,
ArH), 8.75 (app. d, Japp =4 Hz, 1H, ArH), 8.96 (app. d, Japp =7.2 Hz, 1H,
ArH), 9.90 (s, 1H, NH). 13C NMR (100 MHz, CDCl3): δ 19.61, 114.33 (d,
2JF–C =21.1 Hz), 116.82, 121.72, 122.08, 127.41, 128.05, 134.29, 136.39,
5-Fluoro-7-methyl-2-(8-quinolinyl)-2,3-dihydro-1H-isoindol-1-one
1
137.40, 137.49, 138.55, 148.37, 161.33 (d, JF–C =246.4 Hz), 168.10. 19F
1
(2d): Colourless solid; m.p. 178–179 °C. H NMR (400 MHz, CDCl3):
NMR (470 MHz, CDCl3): δ –112.37. HRMS (EI): m/z [M+] calcd for
C18H15FN2O: 294.1168; found: 294.1172.
δ 2.78(s, 3H, Me), 5.22 (s, 2H, CH2), 6.96–7.03 (m, 2H, ArH), 7.43 (q,
J=4 Hz, 1H, ArH), 7.63 (t, J=8 Hz, 1H, ArH), 7.83 (app. d, Japp. =8 Hz,
1H, ArH), 7.91 (app. d, Japp. =7.6 Hz, 1H, ArH), 8.21 (app. d, Japp. =8.4 Hz,
1H, ArH), 8.88 (app. d, Japp. =4 Hz. 1H, ArH). 13C NMR (100 MHz,
CDCl3): δ 17.43, 52.98 (d, 4JF–C =2.8 Hz), 107.24 (d, 2JF–C =23.5 Hz), 117.09
(d, 2JF–C =22.3 Hz), 121.41, 125.76, 126.37, 127.52, 128.83, 129.48, 135.43,
2-Methyl-N-(8-quinolinyl)benzamide (1e): Yield: 0.67 g (93%); pale
brown crystals; m.p. 114–115 °C. 1H NMR (400 MHz, CDCl3): δ 2.61 (s,
3H, Me), 7.33 (t, J=7.6 Hz, 2H, ArH), 7.42 (t, J=7.2 Hz, 1H, ArH), 7.47 (q,
J=4.4 Hz, 1H, ArH), 7.56–7.64 (m, 2H, ArH), 7.69 (app. d, Japp. =7.2 Hz,
1H, ArH), 8.79 (m, 1H, ArH), 8.95 (app. d, Japp. =7.2 Hz, 1H, ArH),
10.24 (s, 1H, NH). 13C NMR (100 MHz, CDCl3): δ 20.27, 116.72, 121.70,
121.85, 126.04, 127.33, 127.53, 128.05, 130.38, 131.40, 134.68, 136.60,
136.73, 138.39, 138.47, 148.21, 168.30. HRMS (EI): m/z [M+] calcd for
C17H14N2O: 262.1106; found: 262.1107.
3
3
136.40, 141.13 (d, JF–C =9.5 Hz), 144.38, 145.44 (d, JF–C = 10.7 Hz),
150.03, 163.54, 168.67 (d, 1JF–C =264 Hz). 19F NMR (470 MHz, CDCl3):
δ–108.168. HRMS (EI): m/z [M+] calcd for C18H13FN2O: 292.1012; found:
292.1010.
2-Acetoxy-6-methyl-N-(8-quinolinyl)benzamide (2e-1): 1e was used
as substrate according to the procedure for the synthesis of isoindolones.
The reaction residue was subjected to silica gel column chromatography,
2e-1 was obtained firstly with PE-EtOAc (7:1) as the eluent, subsequently
2e-2 was obtained with PE-EtOAc (3:1) as the eluent.
2e-1: Pale yellow solid; m.p. 44–45 °C. 1H NMR (400 MHz, CDCl3): δ
2.10 (s, 3H, Me), 2.50(s, 3H, OCOMe), 7.05 (app. d, Japp. =8 Hz, 1H, ArH),
7.19 (app. d, Japp. =7.6 Hz, 1H, ArH), 7.38 (t, J=7.6 Hz, 1H, ArH), 7.46 (q,
J=4 Hz, 1H, ArH), 7.57–7.61 (m, 2H, ArH), 8.19 (app. d, Japp. =8.4 Hz,
1H, ArH), 8.78 (app. d, Japp. =4 Hz. 1H, ArH), 8.93 (app. d, Japp. =6.8 Hz,
1H, ArH), 10.04 (s, 1H, NH). 13C NMR (100 MHz, CDCl3): δ 19.60,
20.86, 116.95, 120.33, 121.77, 122.17, 127.42, 128.01, 128.28, 130.13,
130.68, 134.26, 136.41, 137.59, 138.42, 147.46, 148.42, 164.90, 169.63.
MS: m/z (%)=320 (M+, 94), 177 (3.25), 171 (1.54), 149 (100), 144 (26.72),
135 (24.43). HRMS (EI): m/z [M+] calcd for C19H16N2O3: 320.1161; found:
320.1164.
N,2,4,6,-Tetramethylbenzamide (1f):
A
solution of CH3NH2
(13.6 g, 438 mmol) in ethanol (28 mL) was cooled to 0 °C, then
2,4,6-trimethylbenzoyl chloride (4 g, 21.9 mmol) was added. After the
addition, the reaction mixture was warmed to room temperature, and
stirred for 24 h. The solvent was removed, the residue was extracted with
ethyl acetate (60 mL), the organic layer was washed with water (3 mL),
brine (3 mL×ꢀ3), dried over Na2SO4, concentrated and cooled. The
white crystals that precipitated were collected by filtration. Yield: 0.44 g
1
(91%); white crystals; m.p. 154–156 °C. H NMR (400 MHz, CDCl3):
δ 2.26 (s, 9H, 3Me), 2.99 (d, J=4.8 Hz, 3H, Me), 5.69 (s, 1H, NH), 6.83
(s, 2H, ArH). 13C NMR (100 MHz, CDCl3): δ 19.11, 21.07, 26.41, 128.13,
134.16, 134.88, 138.40, 171.40. HRMS (EI): m/z [M+] calcd for C11H15NO:
177.1154; found: 177.1151.
Substituted 7-methyl-2-(8-quinolinyl)-2,3-dihydro-1H-isoindol-1-ones;
general procedure
2-Acetoxy-6-methyl-N-(7-acetoxy-8-quinolinyl)benzamide
(2e-2):
Amide
1 (0.29 mmol), Pd(OAc)2 (0.0033 g, 5 mol%), PhI(OAc)2
1
Orange solid; m.p. 57–58 °C. H NMR (400 MHz, CDCl3): δ 2.13 (s,
3H, Me), 2.48(s, 6H, 2 OCOMe), 7.05 (app. d, Japp. =8 Hz, 1H, ArH), 7.19
(app. d, Japp. =7.2 Hz, 1H, ArH), 7.36 (m, 2H, ArH), 7.50 (q, J=4.4 Hz, 1H,
ArH), 8.19 (app. d, Japp. =8.4 Hz, 1H, ArH), 8.81 (app. d, Japp. =4.4 Hz. 1H,
ArH), 8.95 (app. d, Japp. =8.4 Hz, 1H, ArH), 9.94 (s, 1H, NH). 13C NMR
(100 MHz, CDCl3): δ 19.56, 20.91, 20.95, 116.25, 119.31, 120.33, 121.99,
128.27, 128.31, 130.18, 130.36, 130.62, 132.60, 137.55, 138.79, 140.99,
147.44, 148.85, 164.80, 169.63, 169.67. MS: m/z (%)=378 (M+, 16.03), 336
(23.36), 202 (11.05), 177 (18.2), 160 (63.71), 149 (14.41), 135 (100). HRMS
(EI): m/z [M+] calcd for C21H18N2O5: 378.1216; found: 378.1213.
(0.2335 g, 2.5 equiv.), HOAc (0.083 mL, 5 equiv.) and mesitylene (1 mL)
were added to a tube, then the reaction mixture was heated under an N2
atmosphere at 120 °C for 24 h. After cooling to room temperature, Et3N
(1.2 mL, 30 equiv.) was added to the reaction mixture. The mixture was
concentrated in vacuo, and the residue was purified by flash column
chromatography to give the corresponding product.
5,7-Dimethyl-2-(8-quinolinyl)-2,3-dihydro-1H-isoindol-1-one
(2a):
1
Pale yellow solid; m.p. 166–168 °C. H NMR (400 MHz, CDCl3): δ
2.45(s, 3H, Me), 2.75 (s, 3H, Me), 5.18 (s, 2H, CH2), 7.07 (s, 1H, ArH),
7.14 (s, 1H, ArH), 7.41–7.44 (m, 1H, ArH), 7.63 (t, J=8 Hz, 1H, ArH),
7.82 (app. d, Japp. =8 Hz, 1H, ArH), 7.91 (app. d, Japp. =7.2 Hz, 1H, ArH),
8.21 (app. d, Japp. =8 Hz, 1H, ArH), 8.88–8.89 (m. 1H, ArH). 13C NMR
(100 MHz, CDCl3): δ 17.34, 21.77, 53.08, 120.66, 121.33, 126.45, 127.13,
127.30, 128.94, 129.48, 130.90, 135.84, 136.50, 137.98, 141.86, 143.53,
144.37, 149.89, 169.72. HRMS (EI): m/z [M+] calcd for C19H16N2O:
288.1263; found: 288.1264.
Electronic Supplementary Information
The 1H and 13C NMR spectra for the compounds described are
available as electronic supplementary information available
from: stl.publisher.ingentaconnect.com/content/stl/jcr/supp-data
This work was financially supported by the National Natural
Science Foundation of China (No. 21262017 ) and a research
project (GJJ10390) from Jiangxi Provincial Department of
Education, P.R. China.
7-Methyl-2-(8-quinolinyl)-2,3-dihydro-1H-isoindol-1-one
(2b):
Colourless solid; m.p. 169–170 °C. 1H NMR (400 MHz, CDCl3): δ 2.80(s,
3H, Me), 5.24 (s, 2H, CH2), 7.25 (m, 1H, ArH), 7.34 (app. d, Japp. =8 Hz,
1H, ArH), 7.43–7.49 (m, 2H, ArH), 7.64 (app. d, Japp. =7.6 Hz, 1H, ArH),
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610 JOURNAL OF CHEMICAL RESEARCH 2013
8
9
P. Hu, Q. Wang, Y. Yan, S. Zhang, B. Zhang and Z. Wang, Org. Biomol.
Chem., 2013, 11, 4304.
J. Neumann, S. Rakshit, T. Droge and F. Glorius, Angew. Chem. Int. Ed.,
2009, 48, 6892.
Received 4 July 2013; accepted 30 July 2013
Paper 1302039 doi: 10.3184/174751913X13801883437178
Published online: 7 October 2013
10 G. He, Y. Zhao, S. Zhang, C. Lu and G. Chen, J. Am. Chem. Soc., 2012,
134, 3.
References
1
T.-S. Mei, L. Kou, S. Ma, K.M. Engle and J.-Q. Yu, Synthesis, 2012, 44,
1778.
11 E.T. Nadres and O. Daugulis, J. Am. Chem. Soc., 2012, 134, 7.
12 M. Ball, A. Boyd, G. Churchill, M. Cuthbert, M. Drew, M. Fielding,
G. Ford, L. Frodsham, M. Golden, K. Leslie, S. Lyons, B. McKeever-
Abbas, A. Stark, P. Tomlin, S. Gottsching, A. Hajar, J. Jiang, J. Lo and B.
Suchozak, Org. Process Res. Dev., 2012, 16, 741.
13 E.J. Yoo, S. Ma, T.-S. Mei, K.S. L. Chan and J.-Q. Yu, J. Am. Chem. Soc.,
2011, 133, 7652.
14 G.-W. Wang, T.-T. Yuan and D.D. Li, Angew. Chem. Int. Ed., 2011, 50,
1380.
2
R. Jazzar, J. Hitee, A. Renaudat, J. Safack-Kreutzer and O. Baudoin,
Chem. Eur. J., 2010, 16, 2654.
3
4
5
6
M. Zhang, A.-Q. Zhang and Y. Peng, J. Organomet. Chem., 2013, 723, 224.
T.W. Lyons and M.S. Sanford, Chem. Rev., 2010, 110, 1147.
J.M. Lee and S. Chang, Tetrahedron Lett., 2006, 47, 1375.
P. Novak, A. Correa, J. Gallardo-Donaire and R. Martin, Angew. Chem.
Int. Ed., 2011, 50, 12236.
7
Y. Li, Z. Li, T. Xiong, Q. Zhang and X. Zhang, Org. Lett., 2012, 14, 3522.
JCR1302039_FINAL.indd 610
04/10/2013 09:17:33

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