Theoretical studies of 5-exo selective intramolecular cyclization of o-alkynylbenzoic acid catalyzed by organic base

Heterocycles

Volumn 74, Issue C, 2007, Pages 819-825

  Terada, Masahiro ^a   Kanazawa, Chikashi ^a   Yamanaka, Masahiro ^b  

^a TOHOKU UNIVERSITY   (Japan)

^b RIKKYO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84962421037     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-07-s(w)73     Document Type: Article

References (35)

1. Gold H.J., and Wilson III C.W. J. Org. Chem. 28 (1963) 985
2. Prager R.H., Tippett J.M., and Ward A.D. Aust. J. Chem. 34 (1981) 1085
3. Clarke S.I., Kasum B., Prager R.H., and Ward A.D. Aust. J. Chem. 36 (1983) 2493
4. Pushan W., Xuanliang G., Yixiong W., Fukuyama Y., Miura I., and Sugawara M. Phytochemistry 23 (1984) 2033
5. Karlsson M.O., Dahlström B., and Neil A. Eur. J. Pharm. 145 (1988) 195
6. del Olmo E., Armas M.G., López-Pérez J.L., Mufioz V., Deharo E., and Feliciano A.S. Bioorg. Med. Chem. Lett. 11 (2001) 2123
7. del Olmo E., Armas M.G., López-Pérez J.L., Ruiz G., Vargas F., Giménez A., Deharo E., and Feliciano A.S. Bioorg. Med. Chem. Lett. 11 (2001) 2755
8. Arai M., Tomoda H., Okuda T., Wang H., Tabata N., Masuma R., Yamaguchi Y., and Omura S. J. Antibiot. 55 (2002) 172
9. Yoganathan K., Rossant C., Ng S., Huang Y., Butler M.S., and Buss A.D. J. Nat. Prod. 66 (2003) 1116
10. Hall J.D., Duncan-Gould N.W., Siddiqi N.A., Kelly J.N., Hoeferlin L.A., Morrison S.J., and Wyatt J.K. Bioorg. Med. Chem. 13 (2005) 1409
11. Zamilpa A., Herrera-Ruiz M., del Olmo E., López-Pérez J.L., Tortoriello J., and Feliciano A.S. Bioorg. Med. Chem. Lett. 15 (2005) 3483
12. Catalyzed by Pd complexes, see:. Liao H.-Y., and Cheng C.-H. J. Org. Chem. 60 (1995) 3711
13. Kundu N.G., Pal M., and Nandi B. Jr. Chem. Soc., Perldn Trans. 1 (1998) 561
14. Sashida H., and Kawamukai A. Synthesis 7 (1999) 1145
15. Rossi R., Bellina F., Biagetti M., Catanese A., and Mannina L. Tetrahedron Lett. 41 (2000) 5281
16. Subramanian V., Batchu V.R., Barange D., and Pal M. J. Org. Chem. 70 (2005) 4778
17. Catalyzed by Ag complexes, see:. Ogawa Y., Maruno M., and Wakamatsu T. Heterocycles 41 (1995) 2587
18. Bellina F., Ciucci D., Vergamini P., and Rossi R. Tetrahedron 56 (2000) 2533
19. Promoted by iodine complex, see:. Biagetti M., Bellina F., Carpita A., Stabile P., and Rossi R. Tetrahedron 58 (2002) 5023
20. Yao T., and Larock R.C. J. Org. Chem. 68 (2003) 5936
21. +]:. Letsinger R.L., Oftedahl E.N., and Nazy J.R. J. Am. Chem. Soc. 87 (1965) 742
22. [Cu]:. Castro C.E., Gaughan E.J., and Owsley D.C. J. Org. Chem. 31 (1966) 4071
23. [Jones Ox.]:. Mukhopadhyay R., and Kundu N.G. Tetrahedron 57 (2001) 9475
24. [Au]:. Marchal E., Uriac P., Legouin B., Toupet L., and van de Weghe P. Tetrahedron 63 (2007) 9979
25. Kanazawa C., and Terada M. Tetrahedron Lett. 48 (2007) 933
26. Uchiyama M., Ozawa H., Takuma K., Matsumoto Y., Yonehara M., Hiroya K., and Sakamoto T. Org. Lett. 8 (2006) 5517
27. Kundu et al. also reported that the 5-exo selective cyclization of la is promoted by NEt3 to give phthalide 2a in low yield (30%). See:. Kundu N.G., Pal M., Nandi B. J. Chem. Soc., Perkin Trans. 1 (1998) 561
28. Hiroya K., Jouka R., Kameda M., Yasuhara A., and Sakamoto T. Tetrahedron 57 (2001) 9697
29. references cited therein;. Asao N., Nogami T., Takahashi K., and Yamamoto Y. J. Am. Chem. Soc. 124 (2002) 764
30. Gabriele B., Salemo G., Fazio A., and Pittelli R. Tetrahedron 59 (2003) 6251
31. Kütt A., Leito I., Kaljurand I., Sooväli L., Vlasov V.M., Yagupolskii L.M., and Koppel I.A. J. Org. Chem. 71 (2006) 2829
32. Kaljurand I., Kütt A., Soovfili L., Rodima T., Mäemets V., Leito I., and Koppel I.A. J. Org. Chem. 70 (2005) 1019
33. Hehre W.J., Radom L., Schleyer P.v.R., and Pople J.A. 'Ab initio Molecular Orbital Theory,' (1986), John Wiley, New York and references cited therein
34. Miertus S., Scrocco E., and Tomasi J. Chem. Phys. 55 (1981) 117
35. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Zakrzewski V.G., Montgomery Jr. J.A., Stratmann R.E., Burant J.C., Dapprich S., Millam J.M., Daniels A.D., Kudin K.N., Strain M.C., Farkas O., Tomasi J., Barone V., Cossi M., Cammi R., Mennucci B., Pomelli C., Adamo C., Clifford S., Ochterski J., Petersson G.A., Ayala P.Y., Cui Q., Morokuma K., Rega N., Salvador P., Dannenberg J.J., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Cioslowski J., Ortiz J.V., Baboul A.G., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Gomperts R., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Andres J.L., Gonzalez C., Head-Gordon M., Replogle E.S., and Pople J.A. 'Gaussian 98, Revision A.11.4,' (2002), Gaussian, Inc., Pittsburgh, PA