An expeditious I2-catalyzed entry into 6H-indolo[2,3-b]quinoline system of cryptotackieine

Journal of Organic Chemistry

Volumn 74, Issue 21, 2009, Pages 8369-8372

  Parvatkar, Prakash T ^a,b   Parameswaran, Perunninakulath S ^a   Tilve, Santosh G ^b  

^a NATIONAL INSTITUTE OF OCEANOGRAPHY   (India)

^b GOA UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL AMINES; CATALYTIC AMOUNTS; CHEMICAL EQUATIONS; DIPHENYL ETHER; ONE POT; QUINOLINE RINGS; REFLUXING;

AMINES; ETHERS; IODINE; ORGANIC COMPOUNDS;

SYNTHESIS (CHEMICAL);

2 METHYL 6H INDOLO[2,3 B]QUINOLINE; 3 BROMO 6H INDOLO[2,3 B]QUINOLINE; 3 METHYL 6H INDOLO[2,3 B]QUINOLINE; 4 METHYL 6H INDOLO[2,3 B]QUINOLINE; 6H INDOLO[2,3 B][1,7]NAPHTHYRIDINE; 6H INDOLO[2,3 B]QUINOLINE; 8H INDOLO[2,3 B]BENZO[F]QUINOLIN; 8H INDOLO[2,3 B]BENZO[H]QUINOLINE; ALKALOID DERIVATIVE; AROMATIC AMINE; CRYPTOTACKIEINE; DIPHENYL ETHER; IMINE; IODINE; NUCLEOPHILE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG; 6H INDOLO(2,3 B)QUINOLINE; 6H-INDOLO(2,3-B)QUINOLINE; CRYPTOTACKIENE; INDOLE ALKALOID; INDOLE DERIVATIVE;

ANNULATION REACTION; ARTICLE; CATALYSIS; DRUG SYNTHESIS; ONE POT SYNTHESIS; SUBSTITUTION REACTION; CHEMISTRY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

CATALYSIS; INDOLE ALKALOIDS; INDOLES; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; QUINOLINES; SPECTROPHOTOMETRY, INFRARED;

EID: 70350707658     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901361x     Document Type: Article

References (26)

1. (a) Molina, A.; Vaquero, J. J.; Garcia-Navio, J. L.; Alvarez-Builla, J.; de Pascual-Teresa, B.; Gago, F.; Rodrigo, M. M.; Ballesteros, M. J. Org. Chem. 1996, 61, 5587-5599.
2. (b) Cimanga, K.; De Bruyne, T.; Pieters, L.; Vlietinck, A. J.; Turger, C. A. J. Nat. Prod. 1997, 60, 688-691.
3. (a) Molina, P.; Alazarin, M.; Vidal, A. J. Chem. Soc., Chem Commun. 1990, 1277-1279.
4. (b) Sundaram, G. S. M.; Venkatesh, C.; Syam Kumar, U. K.; Ila, H.; Junjappa, H. J. Org. Chem. 2004, 69, 5760-5762.
5. (a) Cimanga, K.; De Bruyne, T.; Pieters, L.; Claeys, M.; Vlietinck, A. Tetrahedron Lett. 1996, 37, 1703-1706.
6. (b) Sharaf, M. H. M.; Schiff, P. L. Jr.; Tackie, A. N.; Phoebe, C. H.; Martin, G. E. J. Heterocycl. Chem. 1996, 33, 239-243.
7. (c) Pousset, J.-L.; Martin, M.-T.; Jossang, A.; Bodo, B. Phytochemistry 1995, 39, 735-736.
8. Grellier, P.; Ramiaramanana, L.; Millerioux, V.; Deharo, E.; Schrevel, J.; Frappier, F.; Trigalo, F.; Bodo, B.; Pousset, J. L. Phytotherapy Res. 1996, 10, 317-321.
9. Parvatkar, P. T.; Parameswaran, P. S.; Tilve, S. G. Tetrahedron Lett. 2007, 48, 7870-7872.
10. (a) Lin, C.; Fang, H.; Tu, Z.; Liu, J.-T.; Yao, C.-F. J. Org. Chem. 2006, 71, 6588-6591.
11. (b) Liu, Z.; Liu, L.; Shafiq, Z.; Wu, Y.-C.; Wang, D.; Chen, Y.-J. Tetrahedron Lett. 2007, 48, 3963-3967.
12. (c) Zhang, X.; Rao, W.; Chan, P. W. H. Synlett 2008, 2204-2208.
13. (d) Wang, X.-S.; Li, Q.; Wu, J.-R.; Li, Y.-L. Synth. Commun. 2009, 39, 702-715.
14. Nandha Kumar, R.; Suresh, T.; Mohan, P. S. Tetrahedron Lett. 2002, 43, 3327-3328.
15. Jonckers, T. H. M.; van Miert, S.; Cimanga, K.; Bailly, C.; Colson, P.; De Pauw-Gillet, M.-C.; van den Heuvel, H.; Claeys, M.; Lemiere, F.; Esmans, E. L.; Rozenski, J.; Quirijnen, L.; Maes, L.; Dommisse, R.; Lemiere, G. L. F.; Vlietinck, A.; Pieters, L. J. Med. Chem. 2002, 45, 3497-3508.
16. Peczynska-Czoch, W.; Pognan, F.; Kaczmarek, L.; Boratynski, J. J. Med. Chem. 1994, 37, 3503-3510.
17. Joanna, G.; Wojciech, L.; Bogdan, Z.; Lukasz, K.; Aleksandra, B.-P.; Danuta, D.; Joanna, W.; Adam, O.; Magdalena, S.; Anna, J.; Anna, J.; Arkadiusz, K.; Wanda, P.-C. Anticancer Res. 2005, 25, 2857-2868.
18. Dhanabal, T.; Sangeetha, R.; Mohan, P. S. Tetrahedron 2006, 62, 6258-6263.
19. Patricia, V.-L.; Alajarin, R.; Alvarez-Builla, J.; Vaquero, J. J. Org. Lett. 2006, 8, 415-418.
20. Jonckers, T. H. M.; Maes, B. U. W.; Lemiere, G. L. F.; Rombouts, G.; Pieters, L.; Haemers, A.; Dommisse, R. A. Synlett 2003, 615-618.
21. Shi, C.; Zhang, Q.; Wang, K. K. J. Org. Chem. 1999, 64, 925-932.
22. Molina, P.; Fresneda, P. M.; Delgado, S. Synthesis 1999, 326-329.
23. Alajarin, M.; Molina, P.; Vidal, A. J. Nat. Prod. 1997, 60, 747-748.
24. Timari, G.; Soos, T.; Hajos, G. Synlett 1997, 1067-1068.
25. Schulte, K. E.; Reisch, J.; Stoess, U. Arch. Pharm. 1972, 305, 523-533.
26. Engqvist, R.; Bergnan, J. Org. Prep. Proced. Int. 2004, 36, 386-390.