A regioselective 1,3-dipolar cycloaddition of 2-arylidene-1-tetralones with DPNI

Heteroatom Chemistry

Volumn 10, Issue 4, 1999, Pages 331-336

  Shanmugasundaram, Muthian ^a   Babu, Srinivasarao Arulananda ^a   Raghunathan, Raghavachary ^a   Padma Malar, Ezekiel J ^a  

^a UNIVERSITY OF MADRAS   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000991198     PISSN: 10427163     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1098-1071(1999)10:4<331::AID-HC12>3.0.CO;2-P     Document Type: Article

References (33)

1. (a) Padwa, A., Ed. 1,3-Dipolar Cycloaddition Chemistry; Wiley-Interscience: New York, 1984; Vols. 1 and 2;
2. (b) Curran, D. P., Ed. Advances in Cycloaddition; JAI: Greenwich, 1988; Vol. 1; 1990; Vol. 2;
3. (b) Curran, D. P., Ed. Advances in Cycloaddition; JAI: Greenwich, 1988; Vol. 1; 1990; Vol. 2;
4. (c) Padwa, A., Intermolecular 1,3-Dipolar Cycloaddition. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991, Vol. 4, p 1069.
5. De Shong, P.; Leginus, J. M.; Lander, S. W. J Org Chem 1986, 51, 574.
6. Kametani, T.; Chu, S.-D.; Honda, T. J Chem Soc Perkin Trans 1 1988, 1598.
7. Annuziata, R.; Chinquini, M.; Cozzi, F.; Raimondi, L. Tetrahedron 1987, 43, 4051.
8. (a) Tufariello, J. J Acc Chem Res 1979, 11, 369;
9. (b) Ali, S. A.; Khan, J. H.; Wazeer, M. I. M. Tetrahedron 1988, 44, 5911;
10. (c) Hall, A.; Meldrum, K. P.; Therond, P. R.; Wightman, R. H. Synlett 1997, 123;
11. (d) Goti, A.; Fedi, V.; Nanneli, L.; De Sarlo, F.; Brandi, A. Synlett 1997, 577.
12. (a) Elugero. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: Oxford 1984; Vol. 5;
13. (b) Araino, N.; Miura, J.; Oda, Y.; Nishioka, H. Chem Abstr 1996, 125, 300995h;
14. (c) Harrison, C. R.; Lett, R. M.; Mccann, S. F.; Shapiro, R.; Stevenson, T. M. Chem Abstr 1996, 124, 202246z;
15. (d) Gusar, N. I.; Gulko, L. I.; Gorodetskova, N. R.; Klebanov, B. M. Chem Abstr 1995, 122, 290766f;
16. (e) Pankaj, P.; Sushil, K.; Manish, S.; Hansa, P. IL FARMACO 50, 1995.
17. (a) Martin, G.; Guitian, E.; Castedo, L. J Org Chem 1992, 57, 5907;
18. (b) Dhande, V. P.; Thakwani, P.; Marathe, K. G. Tetrahedron 1988, 44, 3015.
19. Muthu, S.; Maruthamuthu, P.; Ragunathan, R.; Vasudeva Rao, P. R.; Mathews, C. K., Tetrahedron Lett 1994, 35, 1763.
20. Raghunathan, R.; Shanmugasundaram, M.; Bhanumathi, S.; Padma Malar, E. J. Heteroatom Chem 1998, 9, 327.
21. Shanmugasundaram, M.; Raghunathan, R.; Padma Malar, E. J. Heteroatom Chem 1998, 9, 517.
22. Mitsui, S.; Senda, Y.; Saito, H. Bull Chem Soc Japan 1966, 39, 694.
23. Kevill, D. N.; Weiler, D.; Cromwell, N. H. J Org Chem 1964, 29, 1276.
24. Huisgen, R. Angew Chem Int Ed 1963, 2, 604.
25. Fleming, I. Frontier Orbital and Organic Chemical Reactions; Wiley: London 1976.
26. Fujimoto, H.; Fukin, K. In Chemical Reactivity and Reaction Paths; Klopman, G., Ed.; Wiley: London, 1974; p. 23.
27. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J Am Chem Soc 1985, 107, 3902.
28. Stewart, J. J. P. J Comput Chem 1989, 10, 209.
29. Stewart, J. J. P. J Comput Chem 1989, 10, 221.
30. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Peterson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Closlowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. GAUSSIAN 94, Revision D.3; Gaussian, Inc.: Pittsburgh, PA, 1995.
31. (a) Huisgen, R.; Knupfer, H.; Sustmann, R.; Wallbillich, G.; Weberndörfer, V. Chem Ber 1967, 100, 1580;
32. (b) Clovis, J. S.; Eckell, A.; Huisgen, R.; Sustmann, R.; Wallbillich, G.; Weberndörfer, V. Chem Ber 1967, 100, 1593.
33. Huisgen, R.; Seidel, M.; Wallbillich, G.; Knupfer, H. Tetrahedron 1962, 17, 3.