Synthesis of naphthalene amino esters by the blaise reaction of o -alkynylarenenitriles

Journal of Organic Chemistry

Volumn 79, Issue 7, 2014, Pages 3244-3248

  Sakthivel, Karuppusamy ^a   Srinivasan, Kannupal ^a  

^a BHARATHIDASAN UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ESTERIFICATION; ESTERS;

AMINO ESTERS; REFORMATSKY REAGENTS;

NAPHTHALENE;

2 ALKYNYLARENENITRILE; ACETYLENE DERIVATIVE; ESTER DERIVATIVE; NAPHTHALENE AMINO ESTER; NAPHTHALENE DERIVATIVE; NITRILE; POLYCYCLIC AROMATIC HYDROCARBON; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; BLAISE REACTION; CHEMICAL REACTION; REFORMATSKY REACTION; SONOGASHIRA REACTION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 84898075826     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo500137m     Document Type: Article

References (29)

1. Rathke, M. W.; Weipert, P. In Zinc Enolates: The Reformatsky and Blaise Reaction in Comprehensive Organic Reactions; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 2, pp 277-299.
2. Rao, H. S. P.; Rafi, S.; Padmavathy, K. Tetrahedron 2008, 64, 8037
3. Denes, F.; Perez-Luna, A.; Chemla, F. Chem. Rev. 2010, 110, 2366
4. Hoang, C. T.; Nguyen, V. H.; Alezra, V.; Kouklovsky, C. J. Org. Chem. 2008, 73, 1162
5. Hoang, C. T.; Bouillere, F.; Johannesen, S.; Zulauf, A.; Panel, C.; Pouilhes, A.; Gori, D.; Alezra, V.; Kouklovsky, C. J. Org. Chem. 2009, 74, 4177
6. Hertzberg, R.; Moberg, C. J. Org. Chem. 2013, 78, 9174
7. Chun, Y. S.; Lee, K. K.; Ko, Y. O.; Shin, H.; Lee, S.-G. Chem. Commun. 2008, 5098
8. Chun, Y. S.; Ryu, K. Y.; Ko, Y. O.; Hong, J. Y.; Hong, J.; Shin, H.; Lee, S.-G. J. Org. Chem. 2009, 74, 7556
9. Ko, Y. O.; Chun, Y. S.; Kim, Y.; Kim, S. J.; Shin, H.; Lee, S.-G. Tetrahedron Lett. 2010, 51, 6893
10. Chun, Y. S.; Ryu, K. Y.; Kim, J. H.; Shin, H.; Lee, S.-G. Org. Biomol. Chem. 2011, 1317
11. Chun, Y. S.; Lee, J. H.; Kim, J. H.; Ko, Y. O.; Lee, S.-G. Org. Lett. 2011, 13, 6390
12. Chun, Y. S.; Kim, J. H.; Choi, S. Y.; Ko, Y. O.; Lee, S.-G. Org. Lett. 2012, 14, 6358
13. Chun, Y. S.; Xuan, Z.; Kim, J. H.; Lee, S.-G. Org. Lett. 2013, 15, 3162
14. Zhao, M.-N.; Liang, H.; Ren, Z.-H.; Guan, Z.-H. Adv. Synth. Catal. 2013, 355, 221
15. Kim, J. H.; Lee, S.-G. Org. Lett. 2011, 13, 1350
16. Kim, J. H.; Shin, H.; Lee, S.-G. J. Org. Chem. 2012, 77, 1560
17. Chun, Y. S.; Ko, Y. O.; Shin, H.; Lee, S.-G. Org. Lett. 2009, 11, 3414
18. Lorthiois, E. Carbozincation of alkenes and alkynes. In The Chemistry of Organozinc Compounds; Rappoport, Z.; Marek, I., Eds.; Wiley: Chichester, 2006; Part 2, pp 863-978.
19. Lorthiois, E.; Meyer, C. Carbozincation of Alkenes and Alkynes. Patais Chemistry of Functional Groups; Wiley: New York, 2009.
20. Kobayashi, K.; Uneda, T.; Takada, K.; Tanaka, H.; Kitamura, T.; Morikawa, O.; Konishi, H. J. Org. Chem. 1997, 62, 664
21. Reddy, R. S.; Prasad, P. K.; Ahuja, B. B.; Sudalai, A. J. Org. Chem. 2013, 78, 5045
22. Gao, P.; Liu, J.; Wei, Y. Org. Lett. 2013, 15, 2872
23. Ward, R. S. Nat. Prod. Rep. 1999, 16, 75
24. Ragot, J. P.; Steeneck, C.; Alcaraz, M. -L.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 1999, 1073
25. Ukita, T.; Nakamura, Y.; Kubo, A.; Yamamoto, Y.; Kotera, J.; Ikeo, T. J. Med. Chem. 1999, 42, 1293
26. Watson, M. D.; Fechtenkötter, A.; Müllen, K. Chem. Rev. 2001, 101, 1267
27. de Koning, C. B.; Rousseau, A. L.; van Otterlo, W. A. L. Tetrahedron 2003, 59, 7
28. Augustine, J. K.; Bombrun, A.; Atta, R. N. Synlett 2011, 2223
29. Kim, J. H.; Chun, Y. S.; Lee, S.-G. J. Org. Chem. 2013, 78, 11483