Palladium-catalyzed cyclization of benzamides with arynes: application to the synthesis of phenaglydon and N-methylcrinasiadine

Chemical Communications

Volumn 50, Issue 81, 2014, Pages 12116-12119

  Pimparkar, Sandeep ^a   Jeganmohan, Masilamani ^a  

^a INDIAN INSTITUTE OF SCIENCE EDUCATION AND RESEARCH   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE DERIVATIVE; BENZAMIDE; BENZAMIDE DERIVATIVE; BENZENE DERIVATIVE; BENZYNE; FUSED HETEROCYCLIC RINGS; N-METHYLCRINASIADINE; PALLADIUM; PHENANTHRENE DERIVATIVE; PHENANTHRIDONE; CARBOXYLIC ACID;

CATALYSIS; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS; ARTICLE; ARYLATION; CATALYST; CHEMICAL STRUCTURE; HYPOTHESIS; NUCLEOPHILICITY; REACTION ANALYSIS;

ACETONITRILES; BENZAMIDES; BENZENE DERIVATIVES; CATALYSIS; CYCLIZATION; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; PALLADIUM; PHENANTHRENES; STEREOISOMERISM;

EID: 84907820270     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc05252h     Document Type: Article

References (36)

1. F. Aprile-Garcia, M. Antunica-Noguerol, M. L. Budzinski, A. C. Liberman, E. Arzt, Endocr. Connect., 2014, 3,1.
2. S. E. Nasrabady, A. Kuzhandaivel, M. Mladinic, A. Nistri, Cell. Mol. Neurobiol., 2011, 31,503.
3. Z. Jin, Nat. Prod. Rep., 2009, 26,363.
4. J. P. Michael, Nat. Prod. Rep., 1995, 12,465.
5. T. Harayama, H. Akamatsu, K. Okamura, T. Miyagoe, T. Akiyama, H. Abe, Y. Takeuchi, J. Chem. Soc., Perkin Trans. 1, 2001, 523.
6. T. Harayama, Y. Akiyama, K. Nakano, H. Shibaike, A. Akamatsu, H. Hori, H. Abe, Y. Takeuchi, Synthesis, 2002, 237.
7. V. Holl, D. Coelho, D. Weltin, P. Dufour, P. Bischoff, Anticancer Res., 2000, 20,3233.
8. S. Patil, S. Kamath, T. Sanchez, N. Neamati, R. F. Schinazi, J. K. Buolamwini, Bioorg. Med. Chem., 2007, 15,1212.
9. A. K. Mohanakrishnan, P. C. Srinivasan, J. Org. Chem., 1995, 60,1939.
10. R. Kleppinger, C. P. Lillya, C. Yang, J. Am. Chem. Soc., 1997, 119,4097.
11. M. G. Banwell, D. W. Lupton, X. Ma, J. Renner, M. O. Sydnes, Org. Lett., 2004, 6,2741.
12. R. Kleppinger, C. P. Lillya, C. Yang, J. Am. Chem. Soc., 1997, 119,4097.
13. L. M. N. Meseroll, J. R. McKee, M. Zanger, Synth. Commun., 2011, 41,2557.
14. A. Padwa, M. Dimitroff, A. G. Waterson, T. Wu, J. Org. Chem., 1998, 63,3986.
15. H. Suzuki, T. Enya, Y. Hisamatsu, Synthesis, 1997, 1273.
16. T. Furuta, Y. Kitamura, A. Hashimoto, S. Fujii, K. Tanaka, T. Kan, Org. Lett., 2007, 9,183.
17. P. H. Bernardo, W. Fitriyanto, C. L. L. Chai, Synlett, 2007, 1935.
18. R. Ferraccioli, D. Carenzi, O. Rombola, M. Catellani, Org. Lett., 2004, 6,4759.
19. V. Rajeshkumar, T.-H. Lee, S.-C. Chuang, Org. Lett., 2013, 15,1468.
20. C. Lu, A. V. Dubrovskiy, R. C. Larock, J. Org. Chem., 2012, 77,8648.
21. P. Thansandote, M. Lautens, Chem. Eur. J., 2009, 15,5874.
22. T. Satoh, M. Miura, Chem. Eur. J., 2010, 16,11212.
23. G. Song, F. Wang, X. Li, Chem. Soc. Rev., 2012, 41,3651.
24. H. Wang, F. Glorius, Angew. Chem., Int. Ed., 2012, 51,7318.
25. P. B. Arokiam, C. Bruneau, P. H. Dixneuf, Chem. Rev., 2012, 112,5879.
26. L. Ackermann, Acc. Chem. Res., 2014, 47,281.
27. T. W. Lyons, M. S. Sanford, Chem. Rev., 2010, 110,1147.
28. T.-T. Yuan, D.-D. Li, G.-W. Wang, Angew. Chem., Int. Ed., 2011, 50,1380.
29. J. Karthikeyan, C.-H. Cheng, Angew. Chem., Int. Ed., 2011, 50,9880.
30. J. Karthikeyan, R. Haridhadharan, C.-H. Cheng, Angew. Chem., Int. Ed., 2012, 51,12343.
31. N. Senthilkumar, K. Parthasarathy, G. Parthasarathy, C.-H. Cheng, Chem. Asian J., 2013, 8,2175.
32. C. S. Yeung, X. Zhao, N. Borduas, V. M. Dong, Chem. Sci., 2010, 1,331.
33. Y. Himeshima, T. Sonoda, H. Kobayashi, Chem. Lett., 1983, 1211.
34. G. Wurz, O. Hofer, H. Greger, Nat. Prod. Lett., 1993, 3,177.
35. R. Suau, A. I. Gomez, R. Rico, Phytochemistry, 1990, 29,1710.
36. Z. Tu, W. Chu, J. Zhang, C. S. Dence, M. J. Wench, R. H. Mach, Nucl. Med. Biol., 2005, 32,437.