Synthesis of polycyclic sultams by palladium-catalyzed intramolecular cyclization

Synthesis

Volumn , Issue 18, 2009, Pages 3127-3135

  Majumdar, K C ^a   Mondal, Shovan ^a   De, Nirupam ^a  

^a UNIVERSITY OF KALYANI   (India)

Author keywords

Cyclization; Palladium acetate; Sulfonamides; Sultams

Indexed keywords

1-NAPHTHYLAMINE; INTRAMOLECULAR CYCLIZATIONS; LIGAND-FREE; MECHANISTIC STUDIES; PALLADIUM ACETATE; REACTION PATHWAYS; SULFONAMIDES; SULTAMS;

AMIDES; BROMINE COMPOUNDS; CYCLIZATION; PALLADIUM; SULFUR COMPOUNDS;

ORGANOMETALLICS;

1 NAPHTHYLAMINE; 11 METHYL 5,9,15 [1,2]ETHANEDIYL[1]YLIDENE 16H DIBENZO[D,K][1,2]THIAAZACYCLODODECINE 14,14 DIOXIDE; 2 HALOBENZYL BROMIDE DERIVATIVE; ANTIGLAUCOMA AGENT; ANTINEOPLASTIC AGENT; ANTIVIRUS AGENT; BROMINE DERIVATIVE; PALLADIUM; SULFONAMIDE; SULTAM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 70449337404     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1216888     Document Type: Article

References (42)

1. Scozzafava, A.; Owa, T.; Mastrolorenzo, A.; Supuran, C. T. Curr. Med. Chem. 2003, 10, 925;
2. references cited therein. Drews, J. Science 2000, 287, 1960.
3. Hanessian, S.; Sailes, H.; Therrien, E. Tetrahedron 2003, 59, 7047.
4. Zhuang, L.; Wai, J. S.; Embrey, M. W.; Fisher, T. E.; Egbertson, M. S.; Payne, L. S.; Guare, J. P.; Vacca, J. P. Jr.; Hazuda, D. J.; Felock, P. J.; Wolfe, A. L.; Stillmock, K. A.; Witmer, M. V.; Moyer, G.; Schleif, W. A.; Gabryelski, L. J.; Leonard, Y. M.; Lynch, J. J.; Michelson, S. R. Jr.; Young, S. D. J. Med. Chem. 2003, 46, 453.
5. Miller, R. A.; Humphrey, G. R.; Lieberman, D. R.; Ceglia, S. S.; Kennedy, D. J.; Grabowski, E. J. J.; Reider, P. J. J. Org. Chem. 2000, 65, 1399.
6. Wroblewski, T.; Graul, A.; Castaner, J. Drugs Future 1998, 23, 365.
7. Rabasseda, X.; Hopkins, S. J. Drugs Today 1994, 30, 557.
8. Inagaki, M.; Tsuri, T.; Jyoyama, H.; Ono, T.; Yamada, K.; Kobayashi, M.; Hori, Y.; Arimura, A.; Yasui, K.; Ohno, K.; Kakudo, S.; Koizumi, K.; Suzuki, R.; Kato, M.; Kawai, S.; Matsumoto, S. J. Med. Chem. 2000, 43, 2040.
9. McKerrecher, D.; Pike, K. G.; Waring, M. J. WO 2006,125,972, 2006.
10. Brzozowski, Z.; Saczewski, F.; Neamati, N. Bioorg. Med. Chem. Lett. 2006, 16, 5298.
11. Wells, G. J.; Tao, M.; Josef, K. A.; Bihovsky, R. J. Med. Chem. 2001, 44, 3488.
12. Tanimukai, H.; Inui, M.; Harigushi, S.; Kaneko, J. Biochem. Pharmacol. 1965, 14, 961.
13. Silvestri, R.; Marfe, G.; Artico, M.; La Regina, G.; Lavecchia, A.; Novellino, E.; Morgante, M.; Di Stefano, C.; Catalano, G.; Filomeni, G.; Abruzzese, E.; Ciriolo, M. R.; Russo, M. A.; Amadori, S.; Cirilli, R.; La Torre, F.; Salimei, P. S. J. Med. Chem. 2006, 49, 5840.
14. Bravo, R. D.; Canepa, A. S. Synth. Commun. 2002, 32, 3675.
15. Orazi, O. O.; Corral, R. A.; Bravo, R. J. Heterocycl. Chem. 1986, 23, 1701.
16. Katritzky, A. R.; Wu, J.; Rachwal, S.; Rachwal, B.; Macomber, D. W.; Smith, T. P. Org. Prep. Proced. Int. 1992, 24, 463.
17. Lee, J.; Zhong, Y.-L.; Reamer, R. A.; Askin, D. Org. Lett. 2003, 5, 4175.
18. Enders, D.; Moll, A.; Bats, J. W. Eur. J. Org. Chem. 2006, 1271.
19. Chiacchio, U.; Corsaro, A.; Rescifina, A.; Bkaithan, M.; Grassi, G.; Piperno, A. Tetrahedron 2001, 57, 3425.
20. Metz, P.; Seng, D.; Frohlich, R. Synlett 1996, 741.
21. Plietker, B.; Seng, D.; Frohlich, R.; Metz, P. Tetrahedron 2000, 56, 873.
22. Greig, I. R.; Trozer, M. J.; Wright, P. T. Org. Lett. 2001, 3, 369.
23. Zhou, A.; Hanson, P. R. Org. Lett. 2008, 10, 2951.
24. Liu, X.-Y.; Li, C.-H.; Che, C.-M. Org. Lett. 2006, 8, 2707.
25. Dauban, P.; Dodd, R. H. Org. Lett. 2000, 2, 2327.
26. Dauban, P.; Saniere, L.; Aurelie, T.; Dodd, R. H. J. Am. Chem. Soc. 2001, 123, 7707.
27. Sherman, E. S.; Chemler, S. R.; Tan, T. B.; Gerlits, O. Org. Lett. 2004, 6, 1573.
28. Liang, J.-L.; Yuan, S.-X.; Chan, P. W. H.; Che, C.-M. Org. Lett. 2002, 4, 4507.
29. Padwa, A.; Flick, A. C.; Leverett, C. A.; Stengel, T. J. Org. Chem. 2004, 69, 6377.
30. Hopkins, M. J.; Hanson, P. R. Org. Lett. 2008, 10, 2223.
31. Hanson, P. R.; Probst, D. A.; Robinson, R. E.; Yau, M. Tetrahedron Lett. 1999, 40, 4761.
32. Merten, S.; Frohlich, R.; Kataeva, O. Adv. Synth. Catal. 2005, 347, 754.
33. Vasudevan, A.; Tseng, P.-S.; Djuric, S. W. Tetrahedron Lett. 2006, 47, 8591.
34. Rayabarapu, D. K.; Zhou, A.; Jeon, K. O.; Samarakoon, T.; Rolfe, A.; Siddiqui, H.; Hanson, P. R. Tetrahedron 2009, 65, 3180.
35. Majumdar, K. C.; Mondal, S. Tetrahedron Lett. 2007, 48, 6951.
36. Majumdar, K. C.; Mondal, S. Tetrahedron Lett. 2008, 49, 2418.
37. Majumdar, K. C.; Chakravorty, S.; De, N. Tetrahedron Lett. 2008, 49, 3419.
38. Majumdar, K. C.; Chattopadhaya, B.; Ray, K. Tetrahedron Lett. 2007, 48, 7633.
39. Majumdar, K. C.; Chattopadhaya, B.; Nath, S. Tetrahedron Lett. 2008, 49, 1609.
40. Majumdar, K. C.; Mondal, S.; De, N. Synlett 2008, 2851.
41. Reilly, T. P.; Ju, C. Curr. Opin. Allergy Clin. Immunol. 2002, 2, 307. CCDC Ref. No.for the CIF file of 10a: CCDC-693638.
42. Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.