Efficient Synthesis of Quinolo-oxepanes Through [3+2] Cycloaddition Reaction of a,b-Unsaturated Ester with Unstabilized Azomethine Ylides

Nagarajan Saravanan; Maruthapillai Arthanareeswari; Palanisamy Kamaraj; Bitragunta Sivakumar

doi:10.14233/ajchem.2015.18915

Issue

Vol. 27 No. 10 (2015): Vol 27 Issue 10

Issue Published : June 22, 2015

This work is licensed under a Creative Commons Attribution 4.0 International License.

Efficient Synthesis of Quinolo-oxepanes Through [3+2] Cycloaddition Reaction of a,b-Unsaturated Ester with Unstabilized Azomethine Ylides

https://doi.org/10.14233/ajchem.2015.18915

Nagarajan Saravanan

Department of Chemistry, SRM University, Kattankulathur-603 203, India

Maruthapillai Arthanareeswari

Department of Chemistry, SRM University, Kattankulathur-603 203, India

Palanisamy Kamaraj

Department of Chemistry, SRM University, Kattankulathur-603 203, India

Bitragunta Sivakumar

Department of Chemistry, SRM University, Kattankulathur-603 203, India

Corresponding Author(s) : Nagarajan Saravanan

npss82@gmail.com

Asian Journal of Chemistry, Vol. 27 No. 10 (2015): Vol 27 Issue 10
Article Published : June 22, 2015

Abstract

New functionalized quinolo-oxepane were achieved by intramolecular 1,3-dipolar cycloaddition reaction of a,b-unsaturated ester with unstabilized azomethine ylides derived from various a-amino acids with high stereo selectivity and good yields. These derivatives were synthesized via Wittig reaction under mild, neutral conditions in a short duration and consistently good yields. The structures of final compounds were characterized by spectral analysis.

Keywords

Quinolines 1 3-Dipolar cycloaddition Azomethine ylides Wittig reaction

Saravanan, N., Arthanareeswari, M., Kamaraj, P., & Sivakumar, B. (2015). Efficient Synthesis of Quinolo-oxepanes Through [3+2] Cycloaddition Reaction of a,b-Unsaturated Ester with Unstabilized Azomethine Ylides. Asian Journal of Chemistry, 27(10), 3667–3670. https://doi.org/10.14233/ajchem.2015.18915

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References

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I.A. Mohammed and E.V.S. Subrahmanyam, Acta Pharmaceut. Sciencia, 51, 163 (2009).
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S. Goel and Ritu, Indian J. Heterocycl. Chem., 15, 401 (2006).
H. Konda, F. Sakamoto, K. Kawakami and G. Tsukamoto, J. Med. Chem., 31, 221 (1988); doi:10.1021/jm00396a035.
P. Sah, Indian J. Heterocycl. Chem., 10, 13 (1998).
C.M. Hall, H.G. Johnson and J.B. Wright, J. Med. Chem., 17, 685 (1974); doi:10.1021/jm00253a006.
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H.H. Pertz, H.-C. Milhahn and E. Eich, J. Med. Chem., 42, 659 (1999); doi:10.1021/jm981092u.
P. Martin, G.E. Lee, T.B.K. Lee, D.K. Rush, C.A. Wilmot, E. Paulus, U. Elben, J.J. Grome and E. Porsche-Wiebking, J. Med. Chem., 37, 3008 (1994); doi:10.1021/jm00045a004.
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N. Saravanan, M. Arthanareeswari and P. Kamaraj, Int. J. Chem., 34, 1143 (2013).
G.P. Rizzi, J. Org. Chem., 35, 2069 (1970); doi:10.1021/jo00831a098.
J.D. Harling and B.S. Orlek, Tetrahedron, 54, 14905 (1998); doi:10.1016/S0040-4020(98)00932-6.
O. Meth-Cohn, S. Rhouati, B. Tarnowski, A. Robinson and B. Tarnowski, J. Chem. Soc. Perkin Trans. I, 1537 (1981); doi:10.1039/p19810001537.
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doi:10.1016/S0065-2725(08)60332-3.
M. Joucla, J. Mortier and J. Hamelin, Tetrahedron Lett., 26, 2775 (1985); doi:10.1016/S0040-4039(00)94909-8.

References

K.F. Wenckebach, JAMA, 81, 472 (1923); doi:10.1001/jama.1923.02650060042012.

I.A. Mohammed and E.V.S. Subrahmanyam, Acta Pharmaceut. Sciencia, 51, 163 (2009).

R.S. Upadhayaya, J.K. Vandavasi, N.R. Vasireddy, V. Sharma, S.S. Dixit and J. Chattopadhyaya, Bioorg. Med. Chem., 17, 2830 (2009); doi:10.1016/j.bmc.2009.02.026.

S. Goel and Ritu, Indian J. Heterocycl. Chem., 15, 401 (2006).

H. Konda, F. Sakamoto, K. Kawakami and G. Tsukamoto, J. Med. Chem., 31, 221 (1988); doi:10.1021/jm00396a035.

P. Sah, Indian J. Heterocycl. Chem., 10, 13 (1998).

C.M. Hall, H.G. Johnson and J.B. Wright, J. Med. Chem., 17, 685 (1974); doi:10.1021/jm00253a006.

C. Lamazzi, S. Léonce, B. Pfeiffer, P. Renard, G. Guillaumet, C.W. Rees and T. Besson, Bioorg. Med. Chem. Lett., 10, 2183 (2000); doi:10.1016/S0960-894X(00)00427-3.

M. Yanato, Y. Takeuchi, M. Chang, K. Hashigaki, T. Tsuruo, T. Tashiro and S. Tsukagoshi, Chem. Pharm. Bull. (Tokyo), 38, 3048 (1990); doi:10.1248/cpb.38.3048.

E. Lukevics, I. Segal, A. Zablotskaya and S. Germane, Molecules, 2, 180 (1997); doi:10.3390/21200180.

V. Nadaraj, ARKIVOC, 82 (2006); doi:10.3998/ark.5550190.0007.a11.

V.V. Mulwad and M.V. Lohar, Indian J. Chem., 42B, 1937 (2003).

H.H. Pertz, H.-C. Milhahn and E. Eich, J. Med. Chem., 42, 659 (1999); doi:10.1021/jm981092u.

P. Martin, G.E. Lee, T.B.K. Lee, D.K. Rush, C.A. Wilmot, E. Paulus, U. Elben, J.J. Grome and E. Porsche-Wiebking, J. Med. Chem., 37, 3008 (1994); doi:10.1021/jm00045a004.

P. Moller, H. Wallin, U. Vogel, H. Autrup, L. Risom, M.T. Hald, B. Daneshvar, L.O. Dragsted, H.E. Poulsen and S. Loft, Carcinogenesis, 23, 1379 (2002); doi:10.1093/carcin/23.8.1379.

(a) S. Yamaguchi, Heterocycles, 79, 243 (2009); doi:10.3987/REV-08-SR(D)9; (b) N.L. Snyder, H.M. Haines and M.W. Peczuh, Tetrahedron, 62, 9301 (2006); doi:10.1016/j.tet.2006.07.021.

N. Saravanan, M. Arthanareeswari and P. Kamaraj, Int. J. Chem., 34, 1143 (2013).

G.P. Rizzi, J. Org. Chem., 35, 2069 (1970); doi:10.1021/jo00831a098.

J.D. Harling and B.S. Orlek, Tetrahedron, 54, 14905 (1998); doi:10.1016/S0040-4020(98)00932-6.

O. Meth-Cohn, S. Rhouati, B. Tarnowski, A. Robinson and B. Tarnowski, J. Chem. Soc. Perkin Trans. I, 1537 (1981); doi:10.1039/p19810001537.

H. Menasra, A. Kedjadja, A. Debache, S. Rhouati, A. Belfaitah and B. Carboni, Synth. Commun., 35, 2779 (2005); doi:10.1080/00397910500290425.

D.A. Barr, R. Grigg, H.Q.N. Gunaratne, J. Kemp, P. McMeekin and V. Sridharan, Tetrahedron, 44, 557 (1988); doi:10.1016/S0040-4020(01)85844-0.

S. Kathiravan, D. Vijayarajan and R. Raghunathan, Tetrahedron Lett., 51, 3065 (2010); doi:10.1016/j.tetlet.2010.04.017.

O. Tsuge and S. Kanemasa, Adv. Heterocycl. Chem., 45, 231 (1989);

doi:10.1016/S0065-2725(08)60332-3.

M. Joucla, J. Mortier and J. Hamelin, Tetrahedron Lett., 26, 2775 (1985); doi:10.1016/S0040-4039(00)94909-8.

Issue

Vol. 27 No. 10 (2015): Vol 27 Issue 10

Efficient Synthesis of Quinolo-oxepanes Through [3+2] Cycloaddition Reaction of a,b-Unsaturated Ester with Unstabilized Azomethine Ylides

Corresponding Author(s) : Nagarajan Saravanan

Abstract

Keywords

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