Abstract
Synthesis of novel highly substituted cyclopentadienes containing quinoline nucleus is described. The initially prepared Knöevenagel adducts of 2-chloroquinoline-3-carbaldehydes and malononitrile or ethyl cyanoacetate underwent reaction with acetylenecarboxylates and isocyanide in dichloromethane at room temperature within 12 h, affording a variety of the desired products in moderate to good yields. Mild reaction condition, use of simple experimental procedure and prompt isolation of the products are some advantages of this protocol.
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B. Liang, S. Kalidindi, J.A. Porco Jr, C.R.J. Stephenson, Org. Lett. 12, 572 (2010)
B. Ganem, Acc. Chem. Res. 42, 463 (2009)
S.L. Cui, X.F. Lin, Y.G. Wang, Org. Lett. 8, 4517–4520 (2006)
C. Simon, T. Constantieux, J. Rodriguez, Eur. J. Org. Chem., 4957 (2004)
M. Murakami, Angew. Chem. Int. Ed. 42, 718 (2003)
A. Jacobi Von Vangelin, H. Neumann, D. Grdes, S. Klaus, D. Strübing, M. Beller, Chem. Eur. J. 9, 4286 (2003)
G. Balme, E. Bossharth, N. Monterio, N. Eur. J. Org. Chem. 4101 (2003)
K. Kriis, K. Ausmees, T. Pehk, M. Lopp, T.A. Kanger, Org. Lett. 12, 2230 (2010)
A. Dömling, Chem. Rev. 106, 17 (2006)
C. Hulme, V. Gore, Curr. Med. Chem. 10, 51 (2003)
V. Nair, C. Rajesh, A.U. Vinod, S. Bindu, A.R. Sreekanth, J.S. Mathen, L. Balagopal, Acc. Chem. Res. 36, 899 (2003)
I. Ugi, B. Verner, A. Dömling, Molecules 8, 53 (2003)
G. Zhu, Eur. J. Org. Chem. 1133 (2003)
L.H. Zhou, G. Su, W. Zhang, B. Yan, J. Comb. Chem. 11, 1083 (2009)
K. Lu, T. Luo, Z. Xiang, Z. You, R. Fathi, J. Chen, Z. Yang, J. Comb. Chem. 7, 958 (2005)
H. Bienaymé, C. Hulme, G. Oddon, P. Schmidt, Chem. Eur. J. 6, 3321 (2000)
R.V.A. Orru, M. de Greef, Synthesis 1471 (2003)
A. Dömling, I. Ugi, Angew. Chem. Int. Ed. 39, 3168 (2000)
D. Lee, J.K. Sello, S.L. Schreiber, Org. Lett. 2, 709 (2000)
R.W. Armstrong, A.P. Combs, P.A. Tempest, A.D. Brown, A.K. Thomas, Acc. Chem. Res. 29, 123 (1996)
D.G. Hall, S. Manku, F. Wang, J. Comb. Chem. 3, 125 (2001)
K.C. Nicolaou, J.A. Pfefferkorn, H.J. Mitchell, A.J. Roecker, S. Barluenga, G.-Q. Cao, R.L. Affleck, J.E. Lillig, J. Am. Chem. Soc. 122, 9954 (2000)
P.J.T. Reeves, R. Balachandran, K.A. Giuliano, E. Hamel, B.W. Day, J. Am. Chem. Soc. 122, 9391 (2000)
D.L. Boger, B.E. Fink, M.P. Hedrick, J. Am. Chem. Soc. 122, 6382 (2000)
I. Ugi, Angew. Chem. Int. Ed. 1, 8 (1962)
E. Winterfeldt, D. Schumann, H.J. Dillinger, Chem. Ber. 102, 1656 (1969)
A. Shaabani, A.H. Rezayan, A. Rahmat, A. Sarvary, Synlett 1458 (2007)
A.A. Esmaeili, A. Moradi, A. Habibi, Synlett 2307 (2011)
A. Shaabani, A.H. Rezayan, S. Ghasemi, A. Sarvary, Tetrahedron Lett. 50, 1456 (2009)
V. Nair, R. Dhanya, S. Viji, Tetrahedron 61, 5843 (2005)
V. Nair, R.S. Menon, P.B. Beneesh, V. Sreekumar, S. Bindu, Org. Lett. 6, 767 (2004)
V. Nair, A.U. Vinod, N. Abhilash, R.S. Menon, V. Santhi, R.L. Varma, S.M. Viji, R. Srinivas, Tetrahedron 59, 10279 (2003)
A.A. Esmaeili, M. Darbanian, Tetrahedron 59, 5545 (2003)
V. Nair, A.U. Vinod, J.S. Nair, A.R. Sreekanth, N.P. Rath, Tetrahedron Lett. 41, 6675 (2000)
V. Nair, A.U. Vinod, Chem. Commun. 1019 (2000)
V. Nair, A.U. Vinod, C. Rajesh, J. Org. Chem. 66, 4427 (2001)
R.D. Dillard, D.E. Pavey, D.N. Benslay, J. Med. Chem. 16, 251 (1973)
A.A. Joshi, C.L. Viswanathan, Anti-Infect Agents Med Chem 5, 105 (2006)
G.A. Epling, K.Y. Lin, J. Heterocycl. Chem. 24, 853 (1987)
J.C. Craig, P.E. Person, J. Med. Chem. 14, 1221 (1971)
S.I. Alqasoumi, A.M. Al-Taweel, A.M. Alafeefy, E. Noaman, M.M. Ghorab, Eur. J. Med. Chem. 45, 738 (2010)
G.J. Atwell, B.C. Baguley, W.A. Denny, J. Med. Chem. 32, 396 (1989)
A.V. Milyutin, L.R. Amirova, V.É. Kolla, F.Y. Nazmetdinov, L.P. Drovosekova, Y.S. Andreichikov, Pharm. Chem. J. 32, 422 (1998)
D.D. Nekrasov, V.G. Chizh, Y.S. Andreichikov, G.A. Tul’bovich, G.A. Aleksandrova, Pharm. Chem. J. 31, 140 (1997)
J. Bergman, A. Brynolf, Tetrahedron 46, 1295 (1990)
V. Nair, R.S. Menon, P.B. Beneesh, V. Sreekumar, S. Bindu, Org. Lett. 6, 767 (2004)
M. Ghandi, A.T. Ghomi, M. Kubicki, J. Org. Chem. 78, 2611 (2013)
G.-B. Wang, L.-F. Wang, C.-Z. Li, J. Sun, G.-M. Zhou, D.-C. Yang, Res. Chem. Intermed. 38, 77 (2012)
B. Baruah, P.J. Bhuyan, Tetrahedron 65, 7099 (2009)
G.E. Lienhard, W.P. Jencks, J. Am. Chem. Soc. 87, 3863 (1965)
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The authors acknowledge the University of Tehran and Radioisotope Research Group of NSTRI for financial support of this research.
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Ghandi, M., Zarezadeh, N. & Rahimi, S. Synthesis of highly substituted cyclopentadienes containing quinoline nucleus. J IRAN CHEM SOC 12, 1577–1584 (2015). https://doi.org/10.1007/s13738-015-0630-z
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DOI: https://doi.org/10.1007/s13738-015-0630-z