A Facile, Atom-Economical, and One-Pot Pseudo Four-Component Synthesis of Isoxazolylspiro[diindeno[1,2-b;2′,1′-e]pyridine-11,3′-indoline]-2′,10,12-triones Catalyzed by pTSA
Corresponding Author
Eligeti Rajanarendar
Department of Chemistry, Kakatiya University, Warangal, 506009 Telangana, India
E-mail: [email protected]Search for more papers by this authorKammari Thirupathaiah
MVS Govt Degree & PG College, Mahabubnagar, 509001 Telangana, India
Search for more papers by this authorSaini Ramakrishna
Department of Chemistry, Kakatiya University, Warangal, 506009 Telangana, India
Search for more papers by this authorDharavath Nagaraju
Department of Chemistry, Kakatiya University, Warangal, 506009 Telangana, India
Search for more papers by this authorBaireddy Kishore
Department of Chemistry, Kakatiya University, Warangal, 506009 Telangana, India
Search for more papers by this authorCorresponding Author
Eligeti Rajanarendar
Department of Chemistry, Kakatiya University, Warangal, 506009 Telangana, India
E-mail: [email protected]Search for more papers by this authorKammari Thirupathaiah
MVS Govt Degree & PG College, Mahabubnagar, 509001 Telangana, India
Search for more papers by this authorSaini Ramakrishna
Department of Chemistry, Kakatiya University, Warangal, 506009 Telangana, India
Search for more papers by this authorDharavath Nagaraju
Department of Chemistry, Kakatiya University, Warangal, 506009 Telangana, India
Search for more papers by this authorBaireddy Kishore
Department of Chemistry, Kakatiya University, Warangal, 506009 Telangana, India
Search for more papers by this authorAbstract
A facile, atom-economical, and one-pot pseudo four-component method for the synthesis of isoxazolylspiro[diindeno[1,2-b;2′,1′-e]pyridine-11,3′-indoline]-2′,10,12-trione derivatives (14) is described. Prominent advantages of this new method are operational simplicity, excellent yields with high purity, short reaction time, easy workup, and mild conditions.
References and Notes
- 1Bienayme, H.; Hulme, H.; Oddon, C.; Schmitt, G. P Chem Eur J 2000, 6, 3321.
10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO;2-A CAS PubMed Web of Science® Google Scholar
- 2Tietze, L. F.; Modi, A. Med Res Rev 2000, 20, 304.
- 3Nair, V.; Rajesh, C.; Vinod, A. U.; Bindu, S.; Sreekanth, A. R.; Mathen, J. S.; Balagopal, L. Acc Chem Res 2003, 36, 899.
- 4Sundberg, J. R. The Chemistry of Indoles; Academic: New York, 1966.
- 5Joshi, K. C.; Chand, P. Pharmaize 1982, 37, 1.
- 6Da Silva, J. F. M.; Garden, S. J.; Pinto, A. C. J Braz Chem Soc 2001, 12, 273.
- 7Zhu, S.–L.; Ji, S.–J.; Yong, Z. Tetrahedron 2007, 63, 9365.
- 8Ugi, I.; Domling, A.; Werner, B. J Heterocycl Chem 2000, 37, 647.
- 9Bienayme, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem Eur J 2000, 6, 3321.
10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO;2-A CAS PubMed Web of Science® Google Scholar
- 10Ugi, I.; Heck, S. Comb Chem High Throughput Screening 2001, 4, 1.
- 11Zhu, J. Eur J Org Chem 2003 1133.
- 12Weber, L. Curr Med Chem 2002, 9, 1241.
- 13Orru, R. V. A.; de Greef, M. Synthesis 2003 1471.
- 14Domling, A.; Ugi, I. 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
- 15Lee, D.; Sello, J. K.; Schreiber, S. L. Org Lett 2000, 2, 709.
- 16Kang, T.-H.; Matsumoto, K.; Murakami, Y.; Takayama, H.; Kitajima, M.; Aimi, N.; Watanabe, H. Eur J Pharmacol 2002, 444, 39.
- 17Ma, J.; Hecht, S. M. Chem Commun 2004 1190.
- 18Edmondson, S.; Danishefsky, S. J.; Sepp-lorenzinol, L.; Rosen, N. J Am Chem Soc 1999, 12, 2147.
- 19Usui, T.; Kondoh, M.; Cui, C.–B.; Mayumi, T.; Osada, H. Biochem J 1998, 333, 543.
- 20Garcia Prado, E.; Garcia Gimenez, M. D.; De la Puerta Vazquez, R.; Espartero Sanchez, J. L.; Saenzro Driguez, M. T. Phytomedicine 2007, 14, 280.
- 21Zhang, J.; El-Sbabrawy, A.–R. O.; EI-Shanawany, M. A.; Schiff, P. L.; Slatkin, D. J. J Nat Prod 1987, 50, 800.
- 22Miri, R.; Javidnia, K.; Hemmateenejad, B.; Azarpira, A.; Amirgbofran, Z. Bioorg Med Chem 2004, 12, 2529.
- 23Heintzelman, G. R.; Averill, K. M.; Dodd, J. HPCT Int Appl WO2002085894 A1020021031 2002.
- 24Heintzelman, G. R.; Averill, K. M.; Dodd, J. H.; Demarest, K. T.; Tang, Y.; Jackson, P. F. Pat Appl Pubi US2004082578 A1 20040429 2004.
- 25Cooper, K.; Fray, M. J.; Cross, P. E.; Richardson, K. Eur Pat Appl EP,299727 A1 19890118 1989.
- 26Vigante, B.; Ozols, J.; Sileniece, G.; Kimenisa, A.; Duburs, G. U. S. S. R. SU.794006 9810107, 1989.
- 27Safak, C.; Simsek, R.; Atlas, Y.; Boydag, S. Erol, K Bull Chim Farm 1997, 136, 665.
- 28Nugiel, D. A.; Etakorn, A.–M.; Vidwans, A.; Benfield, P. A.; Boisclair, M.; Burton, C. R.; Cox, S.; Czernaik, P. M.; Dolenaik, D.; Seitz, S. P. J Med Chem 2001, 44, 1334.
- 29Faederick, R.; Dumont, W.; Ooms, F.; Ascheabach, L.; Vander Schyf, C. J.; Castagnoli, N.; Woulters, J.; Krief, A. J Med Chem 2006, 49, 3743.
- 30(a) Rajanarendar, E.; Mohan, G.; Ramesh, P.; Kalyan Rao, E. Heterocyclic Commun 2006, 12, 431; (b) Rajanarendar, E.; Rama Krishna, S.; Govardhan Reddy, K.; Nagaraju, D.; Reddy, Y. N. Bioorg Med Chem Lett 2013, 23, 3954.
- 31(a)Rajanarendar, E.; Mohan, G.; Ramesh, P.; Srinivas, M. J Heterocyclic Chem 2007, 44, 215; (b) Rajanarendar, E.; Ramesh, P.; Kalyan Rao, E.; Mohan, G.; Siva Rami Reddy, A. J Heterocyclic Chem 2007, 44, 1153; (c) Rajanarendar, E.; Ramakrishna, S.; Kishore, B. J Heterocyclic Chem 2014, 51, 1415; (d) Rajanarendar, E.; Govardhan Reddy, K.; Ramakrishna, S.; Srinivas, M. J Heterocyclic Chem 2015, 52, 660; (e) Rajanarendar, E.; Nagi Reddy, M.; Rama Krishna, S.; Govardhan Reddy, K.; Reddy, Y. N.; Rajam, M. V. Eur J Med Chem 2012, 50, 344; (f) Rajanarendar, E.; Nagi Reddy, M.; Govardhan Reddy, K.; Ramakrishna, S. Tetrahedron Lett 2012, 53, 2909; (g) Rajanarendar, E.; Nagi Reddy, M.; Ramamurthy, K.; Surendar, P.; Reddy, R. N.; Reddy, Y. N. Bioorg Med Chem Lett 2012, 22, 149; (h) Rajanarendar, E.; Ramakrishna, S.; Ramamurthy, K. Chin Chem Lett 2012, 23, 899.
