A New Four-Component Reaction for the Synthesis of Spiro[4H-indeno[1,2-b]pyridine-4,3′-[3H]indoles]
Afsaneh Feiz
Department of Chemistry, Shahid Beheshti University, G. C. Tehran, 1983963113, Iran
Search for more papers by this authorGhazaleh Imani Shakibaei
Department of Chemistry, Shahid Beheshti University, G. C. Tehran, 1983963113, Iran
Search for more papers by this authorZahra Yasaei
Department of Chemistry, Shahid Beheshti University, G. C. Tehran, 1983963113, Iran
Search for more papers by this authorHamid Reza Khavasi
Department of Chemistry, Shahid Beheshti University, G. C. Tehran, 1983963113, Iran
Search for more papers by this authorCorresponding Author
Ayoob Bazgir
Department of Chemistry, Shahid Beheshti University, G. C. Tehran, 1983963113, Iran
Department of Chemistry, Shahid Beheshti University, G. C. Tehran, 1983963113, IranSearch for more papers by this authorAfsaneh Feiz
Department of Chemistry, Shahid Beheshti University, G. C. Tehran, 1983963113, Iran
Search for more papers by this authorGhazaleh Imani Shakibaei
Department of Chemistry, Shahid Beheshti University, G. C. Tehran, 1983963113, Iran
Search for more papers by this authorZahra Yasaei
Department of Chemistry, Shahid Beheshti University, G. C. Tehran, 1983963113, Iran
Search for more papers by this authorHamid Reza Khavasi
Department of Chemistry, Shahid Beheshti University, G. C. Tehran, 1983963113, Iran
Search for more papers by this authorCorresponding Author
Ayoob Bazgir
Department of Chemistry, Shahid Beheshti University, G. C. Tehran, 1983963113, Iran
Department of Chemistry, Shahid Beheshti University, G. C. Tehran, 1983963113, IranSearch for more papers by this authorAbstract
A new four-component synthesis of spiro[4H-indeno[1,2-b]pyridine-4,3′-[3H]indoles] and spiro[acenaphthylene-1(2H),4′-[4H-indeno[1,2-b]pyridines] by the reaction of indane-1,3-dione, 1,3-dicarbonyl compounds, isatins (=1H-indole-2,3-diones) or acenaphthylene-1,2-dione, and AcONH4 in refluxing toluene in the presence of a catalytic amount of pyridine is reported.
References
- 1 N. K. Terrett, ‘Combinatorial Chemistry’, Oxford University Press, New York, 1998.
- 2 A. Dömling, Curr. Opin. Chem. Biol. 2002, 6, 306.
- 3
A. Dömling, I. Ugi, Angew. Chem., Int. Ed. 2000, 39, 3168.
10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO;2-U CAS PubMed Web of Science® Google Scholar
- 4 A. Dömling, Chem. Rev. 2006, 106, 17.
- 5 A. Shaabani, E. Soleimani, J. Moghimi-Rad, Tetrahedron Lett. 2008, 49, 1277.
- 6 M. C. Pirrung, K. Das Sarma, Tetrahedron 2005, 61, 11456.
- 7 R. J. Sundberg, ‘The Chemistry of Indoles’, Academic, New York, NY, 1996.
- 8 K. C. Joshi, P. Chand, Pharmazie 1982, 37.
- 9 J. F. M. Da Silva, S. J. Garden, A. C. Pinto, J. Braz. Chem. Soc. 2001, 12, 273.
- 10 A. H. Abdel-Rahman, E. M. Keshk, M. A. Hanna, S. M. El-Bady, Bioorg. Med. Chem. 2004, 12, 2483.
- 11 S.-L. Zhu, S.-J. Ji, Z. Yong, Tetrahedron 2007, 63, 9365.
- 12 T.-H. Kang, K. Matsumoto, M. Tohda, Y. Murakami, H. Takayama, M. Kitajima, N. Aimi, H. Watanabe, Eur. J. Pharmacol. 2002, 444, 39.
- 13 J. Ma, S. M. Hecht, Chem. Commun. 2004, 1190.
- 14 T. Usui, M. Kondoh, C.-B. Cui, T. Mayumi, H. Osada, Biochem. J. 1998, 333, 543.
- 15 M. M. Khafagy, A. H. F. A. El-Wahab, F. A. Eid, A. M. El-Agrody, Farmaco 2002, 57, 715.
- 16 J. Zhang, A.-R. O. el-Shabrawy, M. A. el-Shanawany, P. L. Schiff Jr., D. J. Slatkin, J. Nat. Prod. 1987, 50, 800.
- 17 R. Miri, K. Javidnia, B. Hemmateenejad, A. Azarpira, Z. Mirghofran, Bioorg. Med. Chem. 2004, 12, 2529.
- 18 G. R. Heintzelman, K. M. Averill, J. H. Dodd, PCT Int. Appl. WO 2002085894 A1 20021031, 2002.
- 19 G. R. Heintzelman, K. M. Averill, J. H. Dodd, K. T. Demarest, Y. Tang, P. F. Jackson, Pat. Appl. Publ. US 2004082578 A1 20040429, 2004.
- 20 K. Cooper, M. J. Fray, P. E. Cross, K. Richardson, Eur. Pat. Appl. EP 299727 A1 19890118, 1989.
- 21 B. Vigante, J. Ozols, G. Sileniece, A. Kimenis, G. Duburs, U.S.S.R. SU 794006 A119810107, 1989.
- 22 C. Safak, R. Simsek, Y. Altas, S. Boydag, K. Erol, Boll. Chim. Farm. 1997, 136, 665.
- 23 M. Nagarajan, A. Morrell, B. C. Fort, M. R. Meckely, S. Antony, G. Kohlhagen, Y. Pommier, M. Cushman, J. Med. Chem. 2004, 47, 5651.
- 24 S. Ahadi, R. Ghahremanzadeh, P. Mirzaei, A. Bazgir, Tetrahedron 2009, 65, 9316.
- 25 K. Jadidi, R. Ghahremanzadeh, A. Bazgir, J. Comb. Chem. 2009, 11, 341.
- 26 R. Ghahremanzadeh, M. Sayyafi, S. Ahadi, A. Bazgir, J. Comb. Chem. 2009, 11, 393.
- 27 R. Ghahremanzadeh, S. Ahadi, G. Imani Shakibaei, A. Bazgir, Tetrahedron Lett. 2010, 51, 499.
- 28 R. Ghahremanzadeh, G. Imani Shakibaei, S. Ahadi, A. Bazgir, J. Comb. Chem. 2010, 12, 191.
- 29 R. Ghahremanzadeh, T. Amanpour, A. Bazgir, J. Heterocycl. Chem. 2009, 46, 1266.
- 30 R. Ghahremanzadeh, T. Amanpour, M. Sayyafi, A. Bazgir, J. Heterocycl. Chem. 2010, 47, 421.
- 31 R. Ghahremanzadeh, T. Amanpoor, A. Bazgir, J. Heterocycl. Chem. 2010, 47, 46.
- 32 R. G. Redkin, L. A. Shemchuk, V. P. Chernykh, O. V. Shishkin, S. V. Shishkina, Tetrahedron 2007, 63, 11444.
- 33 G. Shanthi, G. Subbulakshmi, P. T Perumal, Tetrahedron 2007, 63, 2057.
- 34 L.-M. Wang, N. Jiao, J. Qiu, J.-J. Yu, J.-Q. Liu, F.-L. Guo, Y. Liu, Tetrahedron 2010, 66, 339.
- 35 M. Dabiri, M. Bahramnejad, M. Baghbanzadeh, Tetrahedron 2009, 65, 9443.
- 36 Y. M. Litvinov, V. Y. Mortikov, A. M. Shestopalov, J. Comb. Chem. 2008, 10, 741.
- 37 X-AREA, Version 1.30, Program for the Acquisition and Analysis of Data, Stoe & Cie GmbH, Darmstadt, Germany, 2005.
- 38 X-RED, Version 1.28b, Program for Data Reduction and Absorption Correction, Stoe & Cie GmbH, Darmstadt, Germany, 2005.
- 39 X-SHAPE, Version 2.05, Program for Crystal Optimization for Numerical Absorption Correction, Stoe & Cie GmbH, Darmstadt, Germany, 2004.
- 40 G. M. Sheldrick, Acta Crystallogr. A 2008, 64, 112.
- 41 X-STEP32, Version 1.07b, Crystallographic Package, Stoe & Cie GmbH, Darmstadt, Germany, 2000.