Organic & Biomolecular Chemistry
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DOI: 10.1039/C3OB41479E
just using KOBut as the base. A variety of substituted
benzimidazole derivatives can be synthesized by the approach.
Moreover, this approach was also applied to the synthesis of
the agonist 7 against the gꢀaminobutyric acid A receptor
(GABAA). Some other reactions of nitriles and the related
applications are ongoing in our laboratory.
We are grateful for the financial supports from National
Natural Science Foundation of China (Nos. 21202109 and
21072140), Sichuan Provincial Department of Education (No.
2011, 76, 654ꢀ660; (c) Y. Fang, Y. Zheng, Z. Wang, Eur. J. Org.
Chem., 2012, 1495ꢀ1498; (d) L.ꢀH. Zou, J. Reball, J. Mottweiler, C.
Bolm, Chem. Commun., 2012, 48, 11307ꢀ11309; (e) F. Diness, D. P.
Fairlie, Angew. Chem. Int. Ed., 2012, 51, 8012ꢀ8016; (f) M. Carmen
PérezꢀAguilar, C. Valdés, Angew. Chem. Int. Ed., 2012, 51, 5953ꢀ
5957; (g) N. Jalalian, T. B. Petersen, B. Olofsson, Chem. Eur. J.,
2012, 18, 14140ꢀ14149; (h) K.C. Majumdar, S. Ganai, R. K. Nandi,
K. Ray, Tetrahedron Lett., 2012, 53, 1553ꢀ1557;
(a) J. Zhao, Y. Zhao, H. Fu, Angew. Chem. Int. Ed., 2011, 50, 3769ꢀ
3773; (b) A. Beyer, C. M. M. Reucher , C. Bolm, Org.Lett., 2011,
13, 2876ꢀ2879; (c) I. Thomé, Carsten Bolm, Org.Lett., 2012, 14,
1892ꢀ1895; (d) A. Beyer, J. Buendia, C. Bolm, Org.Lett., 2012, 14,
3948ꢀ3951; (e) I. Thomꢀ , C. Besson, T. Kleine, C. Bolm, Angew.
Chem. Int. Ed., 2013, 52, 7509ꢀ7513.
70
75
5
5
6
10 11ZA108), Sichuan Province Higher Education System Key
Laboratory of Advanced Functional Materials (KFKT2013ꢀ02)
and Sichuan Normal University.
80
For some KOButꢀpromoted reactions, see: (a) S. Yanagisawa, K.
Ueda, T. Taniguchi, K. Itami, Org. Lett., 2008, 10, 4673ꢀ4676; (b)
C.ꢀL. Sun, H. Li, D.ꢀG. Yu, M. Yu, X. Zhou, X.ꢀY. Lu, K. Huang,
S.ꢀF. Zheng, B.ꢀJ. Li, Z.ꢀJ. Shi, Nat. Chem., 2010, 2, 1044ꢀ1049; (c)
W. Liu, H. Cao, H. Zhang, K. H. Chung, C. He, H. Wang, F. Y.
Kwong, A. Lei, J. Am. Chem. Soc., 2010, 132, 16737ꢀ16740; (d) D.
S. Roman, Y. Takahashi, A. B. Charette, Org. Lett., 2011, 13, 3242ꢀ
3245; (e) C.ꢀL. Sun, Y.ꢀF. Gu, W.ꢀP. Huang, Z.ꢀJ. Shi, Chem.
Commun., 2011, 47, 9813ꢀ9815; (f) M. Rueping, M. Leiendecker, A.
Das, T. Poisson, L. Bui, Chem. Commun., 2011, 47, 10629ꢀ10631;
(g) Y. Qiu, Y. Liu, K. Yang, W. Hong, Z. Li, Z. Wang, Z. Yao, S.
Jiang, Org. Lett., 2011, 13, 3556ꢀ3559; (h) G.ꢀP. Yong, W.ꢀL. She,
Y.ꢀM. Zhang, Y.ꢀZ. Li, Chem. Commun., 2011, 47, 11766ꢀ11768; (i)
E. Shirakawa, X. Zhang, T. Hayashi, Angew. Chem., Int. Ed., 2011,
50, 4671ꢀ4674; (j) C.ꢀL. Sun, Y.ꢀF. Gu, B. Wang, Z.ꢀJ. Shi,
Chem.;Eur. J., 2011, 17, 10844ꢀ10847; (k) H. Liu, B. Yin, Z. Gao,
Y. Li, H. Jiang, Chem. Commun., 2012, 48, 2033ꢀ2035; (l) W.ꢀC.
Chen, Y.ꢀC. Hsu, W.ꢀC. Shih, C.ꢀY. Lee, W.ꢀH. Chuang, Y.ꢀF. Tsai,
P. P.ꢀY. Chen, T.ꢀG. Ong, Chem. Commun., 2012, 48, 6702ꢀ6704;
(m) S. De, S. Ghosh, S. Bhunia, J. A. Sheikh, A. Bisai, Org. Lett.,
2012, 14, 4466ꢀ4469; (n) B. S. Bhakuni, A. Kumar, S. J. Balkrishna,
J. A. Sheikh, S. Konar, S. Kumar, Org. Lett., 2012, 14, 2838ꢀ2841;
(o) Y. Wu, S. M. Wong, F. Mao, T. L. Chan, F. Y. Kwong, Org.
Lett., 2012, 14, 5306ꢀ5309; (p) A. Beyer, J. Buendia, C. Bolm, Org.
Lett., 2012, 14, 3948ꢀ3951; (q) H. Zhang, R. Shi, A. Ding, L. Lu, B.
Chen, A. Lei, Angew. Chem., Int. Ed., 2012, 51, 12542ꢀ12545; (r) M.
E. Budén, J. F. Guastavino, R. A. Rossi, Org. Lett., 2013, 13, 1174ꢀ
1177.
Notes and references
College of Chemistry and Materials Science, Sichuan Normal University,
15 Chengdu 610068, P. R. China. Tel: (+86) 02884766730; E-mail:
xiangsk@hotmail.com; wangbiqin1964@126.com
† Electronic Supplementary Information (ESI) available: See
DOI: 10.1039/b000000x/
85
90
20
25
30
35
40
45
50
55
60
65
1
(a) D. A. Horton, G. T. Bourne, M. L. Smythe, Chem. Rev., 2003,
103, 893ꢀ930; (b) M. Alamgir, D. St. C. Black, N. Kumar, Top.
Heterocycl. Chem., 2007, 9, 87ꢀ118; (c) M. S. Kedar, N. S. Dighe,
S. R. Pattan, D. S. Musmade, D. Thakur, M. Bhosale and V. M.
Gaware, Der Pharma Chemica, 2010, 2, 249ꢀ256; (d) L. Srikanth,
V.Varun Raj, N. Raghunandan and L.Venkateshwerlu, Der Pharma
Chemica, 2011, 3, 172ꢀ193; (e) B. Narasimhan, D. Sharma, P.
Kumar, Med. Chem. Res., 2012, 21, 269ꢀ283.
95
2
For some selected examples in recent years, see: (a) S.ꢀY. Lin, Y.
Isome, E. Stewart, J.ꢀF. Liu, D. Yohannes, L. Yu, Tetrahedron Lett.,
2006, 47, 2883ꢀ2886; (b) L. M. Dudd, E. Venardou, E. Garciaꢀ
Verdugo, P. Licence, A. J. Blake, C. Wilson, M. Poliakoff, Green
Chem., 2003, 5, 187ꢀ192; (c) C. Zhang, L. Zhang, N. Jiao, Green
Chem., 2012, 14, 3273ꢀ3276; (d) M. A. Chari, D. Shobha and T.
Sasaki, Tetrahedron Lett., 2011, 52, 5575ꢀ5580; (e) Y. Riadi, R.
Mamouni, R. Azzalou, M. E. Haddad, S. Routier, G. Guillaumet, S.
Lazar, Tetrahedron Lett., 2011, 52, 3492ꢀ3495; (f) M. A. Chari, D.
Shobha, E.ꢀR. Kenawy, S. S. AlꢀDeyab, B. V. S. Reddy, A. Vinu,
Tetrahedron Lett., 2010, 51, 5195ꢀ5199; (g) K. Bahrami, M. M.
Khodaei, A. Nejatia, Green Chem., 2010, 12, 1237ꢀ1241; (h) J.ꢀP.
Wan, S.ꢀF. Gan, J.ꢀM. Wu, Y. Pan, Green Chem., 2009, 11, 1633ꢀ
1637; (i) D. Saha, A. Saha, B. C. Ranu, Green Chem., 2009, 11,
733ꢀ737; (j) K. Bahrami, M. M. Khodaei, F. Naali, Synlett, 2009,
569ꢀ572; (k) H. Sharghi, M. Aberi, M. M. Doroodmand, Adv. Synth.
Catal., 2008, 350, 2380; (l) C. Mukhopadhyay, P. K. Tapaswi,
Tetrahedron Lett., 2008, 49, 6237; (m) K. Bahrami, M. M. Khodaei,
F. Naali, J. Org. Chem., 2008, 73, 6835.
100
105
110
7
J. L. Falcó, M. Piqué, M. Gonzá, I. Buira, E. Méndez, J. Terencio, C.
Pérez, M. Príncep, A. Palomer, A. Guglietta, Eur. J. Med.Chem.,
2006, 41, 985ꢀ990.
3
(a) N. Zheng, K. W. Anderson, X. Huang, H. N. Nguyen, S. L.
Buchwald, Angew. Chem. Int. Ed., 2007, 46, 7509ꢀ7512; (b) N.
Zheng, S. L. Buchwald, Org. Lett., 2007, 9, 4749ꢀ4751; (c) B. Zou,
Q. Yuan, D. Ma, Angew. Chem. Int. Ed., 2007, 46, 2598ꢀ2601; (d) X.
Diao, Y. Wang, Y. Jiang, D. Ma, J. Org. Chem., 2009, 74, 7974ꢀ
7977; (e) Y. Kim, M. R. Kumar, N. Park, Y. Heo, S. Lee, J. Org.
Chem., 2011, 76, 9577ꢀ9583; (f) G. Evindar, R. A. Batey, Org.Lett.,
2003, 5, 133ꢀ136; (g) C. T. Brain, S. A. Brunton, Tetrahedron Lett.,
2002, 43, 1893ꢀ1895; (h) C. T. Brain, J. T. Steer, J. Org. Chem.,
2003, 68, 6814ꢀ6816; (i) J. Peng, M. Ye, C. Zong, F. Hu, L. Feng,
X. Wang, Y. Wang, C. Chen, J. Org. Chem., 2011, 76, 716ꢀ719; (j)
G. Brasche S. L. Buchwald, Angew. Chem. Int. Ed., 2008, 47, 1932ꢀ
1934; (k) Q. Xiao, W. Wang, G. Liu, F. Meng, J. Chen, Z. Yang, Z.
Shi, Chem. Eur. J., 2009, 15, 7292ꢀ7296; (l) B. C. Wray, J. P.
Stambuli, Org. Lett., 2010, 12, 4576ꢀ4579; (m) X. Deng, N. S. Mani,
Eur. J. Org. Chem., 2010, 680ꢀ686; (n) M. Shen, T. G. Driver, Org.
Lett., 2008, 10, 3367ꢀ3370.
4
(a) Y. Yuan, I. Thomé, S. H. Kim, D. Chen, A. Beyer, J. Bonnamour,
E. Zuidema, S. Chang, C. Bolm, Adv. Synth. Catal., 2010, 352,
2892ꢀ 2898; (b) R. Cano, D. J. Ramón, M. Yus, J. Org. Chem.,
4
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