G
Synthesis
D. Kalsi et al.
Special Topic
(
1
E)-3-(Cyclohexylimino)-2-quinolin-8-yl-2,3-dihydro-1H-isoindol-
-one (3t) and (Z)-3-(Cyclohexylimino)-2-quinolin-8-yl-2,3-dihy-
(2) (a) Zhu, R.-Y.; Farmer, M. E.; Chen, Y.-Q.; Yu, J.-Q. Angew. Chem.
Int. Ed. 2016, 55, 10578. (b) Misal Castro, L. C.; Chatani, N. Chem.
Lett. 2015, 44, 410. (c) Rouquet, G.; Chatani, N. Angew. Chem. Int.
Ed. 2013, 52, 11726.
dro-1H-isoindol-1-one (3t′)
Following the general procedure on a 0.2-mmol scale using cyclohex-
yl isonitrile with purification by flash column chromatography
(
3) Selected reviews on C–H bond functionalization using first-row
transition-metal catalysts, see: (a) Moselage, M.; Li, J.;
Ackermann, L. ACS Catal. 2016, 6, 498. (b) Yoshikai, N. Chem-
CatChem 2015, 7, 732. (c) Liang, Y.; Liang, Y.-F.; Jiao, N. Org.
Chem. Front. 2015, 2, 403. (d) Hyster, T. Catal. Lett. 2015, 145,
(
(
1
EtOAc/hexane, 25:75) gave 3t/3t′ as a colorless oil; yield: 50 mg
70%); ratio E/Z 2.28:1.0; R = 0.45 (EtOAc/hexane).
f
H NMR (CDCl , 400 MHz): δ = 8.87–8.84 (m, 1 H), 8.22–8.16 (m, 1 H),
3
8
7
.04 (d, J = 7.7 Hz, 1 H), 7.96 (d, J = 7.3 Hz, 1 H), 7.91–7.86 (m, 1 H),
.73–7.61 (m, 4 H), 7.38–7.35 (m, 1 H), 4.28–4.23 (m, 1 H), 1.85–1.82
4
58. (e) Cai, X.i. H.; Xie, B. ARKIVOC 2015, (i), 184;
http://www.arkat-usa.org. (f) Bauer, I.; Knölker, H.-J. Chem. Rev.
015, 115, 3170. (g) Tasker, S. Z.; Standley, E. A.; Jamison, T. F.
(m, 1 H), 1.74–1.65 (m, 2 H), 1.64–1.58 (m, 1 H), 1.45–1.18 (m, 6 H).
2
1
3
C NMR (CDCl , 101 MHz): δ = 167.51, 150.30, 149.80, 144.70,
3
Nature (London) 2014, 509, 299. (h) Gao, K.; Yoshikai, N. Acc.
Chem. Res. 2014, 47, 1208. (i) Ackermann, L. J. Org. Chem. 2014,
1
1
36.05, 133.13, 133.04, 132.35, 131.31, 130.95, 130.12, 129.80,
29.09, 128.59, 125.65, 123.96, 121.27, 57.59, 34.03, 25.47, 24.50.
7
9, 8948. (j) Yamaguchi, J.; Muto, K.; Itami, K. Eur. J. Org. Chem.
2013, 19. (k) Gephart, R. T.; Warren, T. H. Organometallics 2012,
1, 7728. (l) Yoshikai, N. Synlett 2011, 1047. (m) Nakao, Y. Chem.
Rec. 2011, 11, 242. (n) Nakamura, E.; Yoshikai, N. J. Org. Chem.
HRMS: m/z [M + H] calcd for C23H22N O: 356.1763; found: 356.2.
3
3
(E)-3-(tert-Butylimino)-5-pyrimidin-2-yl-2-quinolin-8-yl-2,3-di-
2010, 75, 6061. (o) Kulkarni, A. A.; Daugulis, O. Synthesis 2009,
hydro-1H-isoindol-1-one (3v)
4087.
Following the general procedure on a 0.2-mmol scale with purifica-
tion by flash column chromatography (EtOAc/hexane, 40:60) gave 3v
as a white solid; yield: 60 mg (74%); R = 0.50 (EtOAc/hexane).
1
(4) Murahashi, S. J. Am. Chem. Soc. 1955, 77, 6403.
(
5) (a) Grigorjeva, L.; Daugulis, O. Org. Lett. 2014, 16, 4688. (b) Liu,
X.-G.; Zhang, S.-S.; Jiang, C.-Y.; Wu, J.-Q.; Li, Q.; Wang, H. Org.
Lett. 2015, 17, 5404. (c) Ni, J.; Li, J.; Fan, Z.; Zhang, A. Org. Lett.
f
H NMR (CDCl , 400 MHz): δ = 9.31 (s, 1 H), 8.88–8.79 (m, 4 H), 8.19
3
(dd, J = 8.2, 1.7 Hz, 1 H), 8.14 (d, J = 8.0 Hz, 1 H), 7.88 (dd, J = 8.1, 1.3
2
016, 18, 5960.
6) (a) Barsu, N.; Bolli, S. K.; Sundararaju, B. Chem. Sci. 2017, 8,
431. (b) Williamson, P.; Galván, A.; Gaunt, M. J. Chem. Sci. 2017,
8, 2588.
Hz, 1 H), 7.73 (dd, J = 7.4, 1.5 Hz, 1 H), 7.66–7.63 (m, 1 H), 7.38 (dd, J =
8
(
.2, 4.2 Hz, 1 H), 7.30–7.26 (m, 1 H), 1.42 (s, 9 H).
2
1
3
C NMR (CDCl , 101 MHz): δ = 167.2, 163.4, 157.4, 150.1, 147.3,
3
1
1
44.8, 141.5, 136.0, 135.7, 133.0, 131.1, 130.8, 130.0, 128.9, 128.3,
27.1, 125.8, 123.8, 121.1, 119.8, 53.9, 30.6.
(7) For selected recent reviews on isonitrile insertion including C–H
bonds, see: (a) Song, B.; Xu, B. Chem. Soc. Rev. 2017, 46, 1103.
(
b) Nenajdenko, V. Isonitrile Chemistry: Applications in Synthesis
HRMS: m/z [M + H] calcd for C25H22N O: 408.1824; found: 408.1825.
5
and Material Science; Wiley-VCH: Weinheim, 2012. (c) Vlaar, T.;
Ruijter, E.; Maes, B. U.; Orru, R. V. Angew. Chem. Int. Ed. 2013, 52,
7
084. (d) Lang, S. Chem. Soc. Rev. 2013, 42, 4867. (e) Gulevich, A.
Funding Information
V.; Zhadanko, A. G.; Orru, R. V. A.; Nenajdenko, V. G. Chem. Rev.
2
2
010, 110, 5235. (f) Dçmling, A.; Ugi, I. Angew. Chem. Int. Ed.
000, 39, 3168. (g) Isonitrile Chemistry; Academic Press: New
Financial support provided by SERB (EMR2016/000136) to support
this research work is gratefully acknowledged. D.K. thanks IITK, N.B.
York, 1971.
and Pardeep express gratitude to CSIR for their fellowships.
S
E
R
B
E(
M
R
2
0
1
6
0/
0
0
1
3
6)
(
8) (a) Hao, W.; Tian, J.; Li, W.; Huang, Z.; Lei, A. Chem. Asian J. 2016,
11, 1664. (b) Takamatsu, K.; Hirano, K.; Miura, M. Org. Lett.
2
015, 17, 4066. (c) Wang, D.; Cai, S.; Ben, R.; Zhou, Y.; Li, X.;
Supporting Information
Zhao, J.; Wei, W.; Qian, Y. Synthesis 2014, 46, 2045. (d) Zhu, C.;
Xie, W.; Falck, J. R. Chem. Eur. J. 2011, 17, 12591.
Supporting information for this article is available online at
https://doi.org /10.1055/s-0036-1589011.
2
(
9) For C(sp )–H bond functionalization, see: (a) Kalsi, D.; Laskar, R.
S
u
p
p
ortioIgnfrm oaitn
S
u
p
p
ortioIgnfrm oaitn
A.; Barsu, N.; Premkumar, J. R.; Sundararaju, B. Org. Lett. 2016,
18, 4198. (b) Barsu, N.; Sen, M.; Sundararaju, B. Chem. Commun.
References
2016, 52, 1338. (c) Barsu, N.; Kalsi, D.; Sundararaju, B. Chem. Eur.
J. 2015, 21, 9364. (d) Sen, M.; Kalsi, D.; Sundararaju, B. Chem.
Eur. J. 2015, 21, 15529. (e) Kalsi, D.; Sundararaju, B. Org. Lett.
(1) (a) C–H Bond Activation and Catalytic Functionalization I, Topics
in Organometallic Chemistry; Dixneuf, P. H.; Doucet, H., Eds.;
Springer: Berlin, 2016. (b) Ye, B.; Cramer, N. Acc. Chem. Res.
2015, 17, 6118.
3
(10) For C(sp )–H bond functionalization, see: (a) Sen, M.;
Emayavaramban, B.; Barsu, N.; Premkumar, J. R.; Sundararaju, B.
ACS Catal. 2016, 6, 2792. (b) Barsu, N.; Rahman, M. A.; Sen, M.;
Sundararaju, B. Chem. Eur. J. 2016, 22, 9135.
(11) See selected recent reports on cobalt(III)-catalyzed C–H bond
functionalization: (a) Prakash, S.; Muralirajan, K.; Cheng, C.-H.
Angew. Chem. Int. Ed. 2016, 55, 1844. (b) Du, C.; Li, P.-X.; Zhu, X.;
Suo, J.-F.; Niu, J.-L.; Song, M.-P. Angew. Chem. Int. Ed. 2016, 55,
13571. (c) Maity, S.; Kancherla, R.; Dhawa, U.; Hoque, E.;
Pimparkar, S.; Maiti, D. ACS Catal. 2016, 6, 5493. (d) Lerchen, A.;
Vásquez-Céspedes, S.; Glorius, F. Angew. Chem. Int. Ed. 2016, 55,
3208. (e) Tan, G.; He, S.; Huang, X.; Liao, X.; Cheng, Y.; You, J.
Angew. Chem. Int. Ed. 2016, 55, 10414. (f) Manoharan, R.;
2
(
5
(
(
(
015, 48, 1308. (c) Ackermann, L. Acc. Chem. Res. 2014, 47, 281.
d) Girard, S. A.; Knauber, T.; Li, C. J. Angew. Chem. Int. Ed. 2014,
3, 74. (e) Collins, K. D.; Glorius, F. Nat. Chem. 2013, 5, 597.
f) Corbet, M.; Decampo, F. Angew. Chem. Int. Ed. 2013, 52, 9896.
g) Li, B.; Dixneuf, P. H. Chem. Soc. Rev. 2013, 42, 5744.
h) Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem. Int.
Ed. 2012, 51, 8960. (i) Neufeldt, S. R.; Sanford, M. S. Acc. Chem.
Res. 2012, 45, 936. (j) Arockiam, P. B.; Bruneau, C.; Dixneuf, P. H.
Chem. Rev. 2012, 112, 5879. (k) Satoh, T.; Miura, M. Chem. Eur. J.
2010, 16, 11212. (l) Colby, D. A.; Bergman, R. G.; Ellman, J. A.
Chem. Rev. 2010, 110, 624.
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Georg Thieme Verlag Stuttgart · New York — Synthesis 2017, 49, A–H