Trifluoroacetylation-induced houben?hoesch-type cyclization of cyanoacetanilides: Increased nucleophilicity of CN groups

Journal of Organic Chemistry

Volumn 75, Issue 8, 2010, Pages 2741-2744

  Kobayashi, Yusuke ^a   Katagiri, Kosuke ^a   Azumaya, Isao ^a   Harayama, Takashi ^a  

^a TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DIRECT OBSERVATION; ELECTRON DENSITIES; GOOD YIELD; NUCLEOPHILICITIES; REACTION MECHANISM; TRIFLUOROACETIC ANHYDRIDES;

REACTION INTERMEDIATES;

ACETANILIDE DERIVATIVE; CYANOACETANILIDE DERIVATIVE; NITRILE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; REACTION OPTIMIZATION; SYNTHESIS;

ACETYLATION; CYCLIZATION; FLUORINE; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NITRILES; QUINOLINES;

EID: 77951001302     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100220m     Document Type: Article

References (36)

1. Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893-930
2. Michael, J. P. Nat. Prod. Rep. 2008, 25, 166-187
3. Barr, S. A.; Boyd, D. R.; Sharma, N. D.; Loke, P. L. Heterocycles 2009, 79, 831-850
4. For reviews of Friedel?Crafts and related reactions, see: Olah, G. A. Friedel?Crafts Chemistry; Wiley-Interscience: New York, 1973.
5. Heaney, H. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 733 ? 752 and 753 ? 768.
6. For a review, see: Larock, R. C. Comprehensive Organic Transformations, 2 nd ed.; Wiley-VCH: New York, 1999; pp 1422 ? 1433.
7. For intramolecular Friedel?Crafts acylation of Meldrums acid derivatives, see: Fillion, E.; Fishlock, D. Tetrahedron 2009, 65, 6682-6695
8. Fillion, E.; Dumas, A. M. J. Org. Chem. 2008, 73, 2920-2923
9. Fillion, E.; Fishlock, D. J. Am. Chem. Soc. 2005, 127, 13144-13145
10. Fillion, E.; Fishlock, D. Org. Lett. 2003, 5, 4653-4656
11. For Houben?Hoesch reactions, see: Spoerri, P. E.; DuBois, A. S. Org. React. 1949, 5, 387-412
12. Sato, Y.; Yato, M.; Ohwada, T.; Saito, S.; Shudo, K. J. Am. Chem. Soc. 1995, 117, 3037-3043
13. Nakamura, S.; Sugimoto, H.; Ohwada, T. J. Org. Chem. 2008, 73, 4219 ? 4224 and references cited therein.
14. For the Pd-catalyzed addition of aromatic C?H bonds to nitriles, see: Zhou, C.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 2302-2303
15. Zhou, C.; Larock, R. C. J. Org. Chem. 2006, 71, 3551-3558
16. Kobayashi, Y.; Harayama, T. Tetrahedron Lett. 2009, 50, 6665-6667
17. Cyanoacetanilides 1a ? f were easily prepared, purified, and obtained as solids, see: Kobayashi, Y.; Harayama, T. Org. Lett. 2009, 11, 1603-1606
18. Welch, J. T.; Eswarakrishnan, S. Fluorine in Bioorganic Chemistry; Wiley: New York, 1991.
19. Hiyama, T. Organofluorine Compounds. Chemistry and Application; Springer: Berlin, 2000.
20. Kirsch, P. Modern Fluoroorganic Chemistry, Synthesis, Reactivity, Applications; Wiley-VCH: Weinheim, 2004.
21. Chambers, R. D. Fluorine in Organic Chemistry; Blackwell: Oxford, 2004.
22. MeCN, DMSO, and THF were also ineffective solvents.
23. Pederson, B. F.; Pederson, B. Tetrahedron Lett. 1965, 6, 2995-3001
24. Nanjan, M. J.; Kannappan, V.; Ganesan, R. Indian J. Chem. 1979, 18B, 461-463
25. Itai, A.; Toriumi, Y.; Tomioka, N.; Kagechika, H.; Azumaya, I.; Shudo, K. Tetrahedron Lett. 1989, 30, 6177-6180
26. ?1. See: Hatsuda, M.; Seki, M. Tetrahedron 2005, 61, 9908-9917
27. CCDC 763341 (9) and CCDC 763342 (15) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.
28. Lamarre, C.; Stella, L. Synlett 1999, 725-726
29. Mekhalfia, A.; Mutter, R.; Heal, W.; Chen, B. Tetrahedron 2006, 62, 5617-5625
30. 2O; see ref 15b.
31. 4 CN); see: Reference 7.
32. Nakao, Y.; Oda, S.; Hiyama, T. J. Am. Chem. Soc. 2004, 126, 13904-13905
33. Moorthy, J. N.; Singhal, N. J. Org. Chem. 2005, 70, 1926-1929
34. Tobisu, M.; Kita, Y.; Ano, Y.; Chatani, N. J. Am. Chem. Soc. 2008, 130, 15982-15989
35. Haddenham, D.; Pasumansky, L.; DeSoto, J.; Eagon, S.; Singaram, B. J. Org. Chem. 2009, 74, 1964-1970
36. Bonnamour, J.; Bolm, C. Chem.?Eur. J. 2009, 15, 4543-4545