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β-Cyclodextrin Mediated Multicomponent Synthesis of Spiroindole Derivatives in Aqueous Medium
Corresponding Author(s) : Vishwa Deepak Tripathi
Asian Journal of Chemistry,
Vol. 32 No. 2 (2020): Vol 32 Issue 2
Abstract
An efficient β-cyclodextrin catalyzed multicomponent synthetic protocol has been developed for the
synthesis of spiro[indoline-3,2'-quinazoline]-2,4'(3’H)-dione from isatoic anhydride, isatin and primary
amine in aqueous medium. This methodology offers a convenient method for the synthesis of spiroindole
quinazolines in excellent yields. To extend synthetic utility of protocol some dihydro quinazolines
have been also synthesized.
Keywords
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- R.V. Hangarge, S.A. Sonwane, D.V. Jarikote and M.S. Shingare, Green Chem., 3, 310 (2001); https://doi.org/10.1039/b106871g.
- S. Feng, J. Zhai and L. Jiang, Angew. Chem. Int. Ed., 44, 5115 (2005); https://doi.org/10.1002/anie.200501337.
- J.E. Klijn and J.B.F.N. Engberts, Nature, 435, 746 (2005); https://doi.org/10.1038/435746a.
- A. Chanda and V.V. Fokin, Chem. Rev., 109, 725 (2009); https://doi.org/10.1021/cr800448q.
- X.-W. Feng, C. Li, N. Wang, K. Li, W.-W. Zhang, Z. Wang and X.-Q. Yu, Green Chem., 11, 1933 (2009); https://doi.org/10.1039/b914653a.
- S.A. Nepogodiev and J.F. Stoddart, Chem. Rev., 98, 1959 (1998); https://doi.org/10.1021/cr970049w.
- K. Takahashi, Chem. Rev., 98, 2013 (1998); https://doi.org/10.1021/cr9700235.
- R. Breslow and S.D. Dong, Chem. Rev., 98, 1997 (1998); https://doi.org/10.1021/cr970011j.
- B.B. Touré and D.G. Hall, Chem. Rev., 109, 4493 (2009); https://doi.org/10.1021/cr800296p
- A.H. Abdel-Rahman, E.M. Keshk, M.A. Hanna and Sh.M. El-Bady, Bioorg. Med. Chem., 12, 2483 (2004); https://doi.org/10.1016/j.bmc.2003.10.063.
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- E.B. Skibo, I. Islam, M.J. Heileman and W.G. Schulz, J. Med. Chem., 37, 78 (1994); https://doi.org/10.1021/jm00027a010.
- C. Lacy and P.J. Scheuer, J. Nat. Prod., 63, 119 (2000); https://doi.org/10.1021/np9902643.
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- J.F.M. Silva, S.J. Garden and A.C. Pinto, J. Braz. Chem. Soc., 12, 273 (2001); https://doi.org/10.1590/S0103-50532001000300002.
- F. Lepage, F. Tombret, G. Cuvier, A. Marivain and J.M. Gillardin, Eur. J. Med. Chem., 27, 581 (1992); https://doi.org/10.1016/0223-5234(92)90137-P.
- A.A. Mohammadi, M. Dabiri and H. Qaraat, Tetrahedron, 65, 3804 (2009); https://doi.org/10.1016/j.tet.2009.02.037.
- G. Wenz, Angew. Chem. Int. Ed. Engl., 33, 803 (1994); https://doi.org/10.1002/anie.199408031.
- K. Surendra, N.S. Krishnaveni and K.R. Rao, Tetrahedron Lett., 47, 2133 (2006); https://doi.org/10.1016/j.tetlet.2006.01.125.
- K. Odashima, A. Itai, Y. Iitaka and K. Koga, J. Am. Chem. Soc., 102, 2504 (1980); https://doi.org/10.1021/ja00527a083.
- A. Kumar, V.D. Tripathi and P. Kumar, Green Chem., 13, 51 (2011); https://doi.org/10.1039/C0GC00523A.
- A. Khalafi-Nezhad and F. Panahi, Green Chem., 13, 2408 (2011); https://doi.org/10.1039/C1GC15360A.
- J. Szejtli, Chem. Rev., 98, 1743 (1998); https://doi.org/10.1021/cr970022c.
- G. Chen and M. Jiang, Chem. Soc. Rev., 40, 2254 (2011); https://doi.org/10.1039/C0CS00153H.
References
R.V. Hangarge, S.A. Sonwane, D.V. Jarikote and M.S. Shingare, Green Chem., 3, 310 (2001); https://doi.org/10.1039/b106871g.
S. Feng, J. Zhai and L. Jiang, Angew. Chem. Int. Ed., 44, 5115 (2005); https://doi.org/10.1002/anie.200501337.
J.E. Klijn and J.B.F.N. Engberts, Nature, 435, 746 (2005); https://doi.org/10.1038/435746a.
A. Chanda and V.V. Fokin, Chem. Rev., 109, 725 (2009); https://doi.org/10.1021/cr800448q.
X.-W. Feng, C. Li, N. Wang, K. Li, W.-W. Zhang, Z. Wang and X.-Q. Yu, Green Chem., 11, 1933 (2009); https://doi.org/10.1039/b914653a.
S.A. Nepogodiev and J.F. Stoddart, Chem. Rev., 98, 1959 (1998); https://doi.org/10.1021/cr970049w.
K. Takahashi, Chem. Rev., 98, 2013 (1998); https://doi.org/10.1021/cr9700235.
R. Breslow and S.D. Dong, Chem. Rev., 98, 1997 (1998); https://doi.org/10.1021/cr970011j.
B.B. Touré and D.G. Hall, Chem. Rev., 109, 4493 (2009); https://doi.org/10.1021/cr800296p
A.H. Abdel-Rahman, E.M. Keshk, M.A. Hanna and Sh.M. El-Bady, Bioorg. Med. Chem., 12, 2483 (2004); https://doi.org/10.1016/j.bmc.2003.10.063.
S. Ryng, Z. Machon, Z. Wieczorek, M. Zimecki and M. Mokrosz, Eur. J. Med. Chem., 33, 831 (1998); https://doi.org/10.1016/S0223-5234(99)80035-X.
E.B. Skibo, I. Islam, M.J. Heileman and W.G. Schulz, J. Med. Chem., 37, 78 (1994); https://doi.org/10.1021/jm00027a010.
C. Lacy and P.J. Scheuer, J. Nat. Prod., 63, 119 (2000); https://doi.org/10.1021/np9902643.
A.A. Raj, R. Raghunathan, M.R. Sridevi Kumari and N. Raman, Bioorg. Med. Chem., 11, 407 (2003); https://doi.org/10.1016/S0968-0896(02)00439-X.
R. Ranjith Kumar, S. Perumal, P. Senthilkumar, P. Yogeeswari and D. Sriram, Eur. J. Med. Chem., 44, 3821 (2009); https://doi.org/10.1016/j.ejmech.2009.05.010.
J.F.M. Silva, S.J. Garden and A.C. Pinto, J. Braz. Chem. Soc., 12, 273 (2001); https://doi.org/10.1590/S0103-50532001000300002.
F. Lepage, F. Tombret, G. Cuvier, A. Marivain and J.M. Gillardin, Eur. J. Med. Chem., 27, 581 (1992); https://doi.org/10.1016/0223-5234(92)90137-P.
A.A. Mohammadi, M. Dabiri and H. Qaraat, Tetrahedron, 65, 3804 (2009); https://doi.org/10.1016/j.tet.2009.02.037.
G. Wenz, Angew. Chem. Int. Ed. Engl., 33, 803 (1994); https://doi.org/10.1002/anie.199408031.
K. Surendra, N.S. Krishnaveni and K.R. Rao, Tetrahedron Lett., 47, 2133 (2006); https://doi.org/10.1016/j.tetlet.2006.01.125.
K. Odashima, A. Itai, Y. Iitaka and K. Koga, J. Am. Chem. Soc., 102, 2504 (1980); https://doi.org/10.1021/ja00527a083.
A. Kumar, V.D. Tripathi and P. Kumar, Green Chem., 13, 51 (2011); https://doi.org/10.1039/C0GC00523A.
A. Khalafi-Nezhad and F. Panahi, Green Chem., 13, 2408 (2011); https://doi.org/10.1039/C1GC15360A.
J. Szejtli, Chem. Rev., 98, 1743 (1998); https://doi.org/10.1021/cr970022c.
G. Chen and M. Jiang, Chem. Soc. Rev., 40, 2254 (2011); https://doi.org/10.1039/C0CS00153H.