One-pot synthesis of five- or six-membered carbocycles through intramolecular cycloadditions by the use of ethyl chloroformate

Tetrahedron

Volumn 55, Issue 23, 1999, Pages 7115-7128

  Liu, Ju Tsung ^a   Lin, Wen Wei ^a   Jang, Jeong Jiunn ^a   Liu, Jing Yuan ^a   Yan, Ming Chung ^a   Hung, Chihua ^a   Kao, Kuo Hsi ^a   Wang, Yeh ^a   Yao, Ching Fa ^a  

^a NATIONAL TAIWAN NORMAL UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

3,3A,4,5,6,7 HEXAHYDRO 7 (2 PHENYLETHYL)CYCLOHEXA[C]ISOXAZOLE; 3,3A,4,5,6,7 HEXAHYDRO 7 (4 FLUOROPHENYL)CYCLOHEXA[C]ISOXAZOLE; 3,3A,4,5,6,7 HEXAHYDRO 7 (N PHENYL 3 INDOLYL)CYCLOHEXA[C]ISOXAZOLE; 3A,4,5,6 TETRAHYDRO 6 (2 PHENYLETHYL) 3H CYCLOPENTA[C]ISOXAZOLE; CHLOROFORMIC ACID ETHYL ESTER; ISOXAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; DECARBOXYLATION; ESTERIFICATION; ISOMERISM; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0033522857     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00351-8     Document Type: Article

References (45)

1. (a) Corey, E. J.; Estreicher, H. J. Am. Chem. Soc. 1978, 100, 6294.
2. (b) Seebach, D.; Colvin, E. W.; Well, T. Chimia 1979, 33, 1.
3. (c) Barrett, A. G. M.; Graboski, G. G. Chem. Rev. 1986, 86, 751.
4. (d) Rosini, G.; Ballini, R. Synthesis 1988, 833.
5. (e) Several articles in Tetrahedron Symposia-in-Print 41, "Nitroalkanes and nitroalkenes in synthesis", Tetrahedron 1990, 46 (21), Barrett, A. G. M. Ed.
6. (f) Barrett, A. G. M. Chem. Soc. Rev. 1991, 20, 95.
7. (a) Torsell, K. B. G. Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis, VCH; New York, 1988.
8. (b) Gottlieb, L.; Hassner, A. J. Org. Chem. 1995, 60, 3759.
9. (c) Dehaen, W.; Hassner, A. Tetrahedron Lett. 1990, 31, 743.
10. (a) Mukaiyama, T.; Hoshino, T. J. Am. Chem. Soc. 1960, 82, 5339.
11. (b) Basel, Y; Hassner, A. Synthesis 1997, 309.
12. (c) Maugein, N.; Wagner, A.; Mioskowski, C. Tetrahedron Lett. 1997, 38, 1547.
13. (a) Kumaran, G.; Kulkarni, G. H. Tetrahedron Lett. 1994, 35, 5517.
14. (b) Kumaran, G.; Kulkarni, G. H. Tetrahedron Lett. 1994, 35, 9099.
15. (c) Kumaran, G.; Kulkarni, G. H. J. Org. Chem. 1997, 62, 1516.
16. (a) Padwa, A. In 1,3-dipolar Cycloaddition Chemistry; Padwa, A.; Ed.; Wiley-Interscience; New York, 1984; Vol. 2.
17. (b) Curran, D. P. Advances in Cycloaddition, Vol. 1, JAI Press; Greenwich, CT, 1988; p 129-189.
18. (a) Hassner, A.; Maurya, R.; Padwa, A.; Bullock, W. H. J. Org. Chem. 1991, 56, 2775.
19. (b) Hassner, A.; Maurya, R.; Mesko, E. Tetrahedron Lett. 1988, 29, 5313.
20. (c) Hassner, A.; Maurya, R. Tetrahedron Lett. 1989, 30, 5803.
21. (d) Grigg, R. Chem. Soc. Rev. 1987, 16, 89.
22. (e) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron Lett. 1990, 31, 559.
23. (a) Buckley, G. D. J. Chem. Soc. 1947, 1494.
24. (b) Buckley, G. D.; Ellery, E. J. Chem. Soc. 1947, 1497.
25. (c) Ashwood, M. S.; Bell, L. A.; Houghton, P. G.; Wright, S. H. B. Synthesis 1988, 379.
26. (a) Yao, C.-F.; Chen, W.-C.; Lin, Y.-M. Tetrahedron Lett. 1996, 37, 6339.
27. (b) Yao, C.-F.; Yang, C.-S.; Fang, H.-Y. Tetrahedron Lett. 1997, 38, 6419.
28. (c) Yao, C.-F.; Kao, K.-H.; Liu, J.-T.; Chu, C.-M.; Wang, Y.; Chen, W.-C.; Lin, Y.-M.; Lin, W.-W.; Yan, M.-C.; Liu, J.-Y.; Chuang, M.-C.; Shiue, J.-L. Tetrahedron 1998, 54, 791.
29. (d) Kao, K.-H.; Yang, C.-S.; Liu, J.-T.; Lin, W.-W.; Fang, H.-Y; Yao, C.-F.; Chen, K. Tetrahedron 1998, 54, 13997.
30. Namboothiri, I. N. N.; Hassner, A.; Gottlieb, H. E. J. Org. Chem. 1997, 62, 485.
31. (a) Christl, M.; Huisgen, R. Chem. Ber. 1973, 106, 3345.
32. (b) Just, G.; Dahl, K. Tetrahedron 1968, 24, 5251.
33. (c) Rai, K. M. L.; Linganna, N.; Hassner, A.; Murthy, C. A. Org. Prep. Proced. Int. 1992, 24, 91.
34. (a) Grundmann, C.; Dean, J. M. J. Org. Chem. 1965, 30, 2809.
35. (b) Hassner, A.; Rai, K. M. L. Synthesis 1989, 57.
36. (c) Kim, J. N.; Ryu, E. K. Synth. Commun. 1990, 20, 1373.
37. Shimizu, T.; Hayashi, Y.; Shibafuchi, H.; Teramura, K. Bull. Chem. Soc. Jpn. 1986, 59, 2827.
38. Armstrong, P.; Grigg, R.; Heaney, F.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1991, 47, 4495.
39. (a) Tufariello, J. J.; Ali, Sk. A. Tetrahedron Lett. 1978, 4647.
40. (b) Tufariello, J. J.; Puglis, J. M. Tetrahedron Lett. 1986, 27, 1265.
41. (c) Burdisso, M.; Gandolfi, R.; Grünanger, P.; Rastelli, A. J. Org. Chem. 1990, 55, 3427.
42. (d) Jung, M. E.; Gervay, J. Chemtracts 1990, 3, 284.
43. Bordwell, F. G.; Garbisch, Jr. E. W. J. Org. Chem. 1962, 27, 3049.
44. (a) Wollenberg, R. H.; Miller, S. J. Tetrahedron Lett. 1978, 3219.
45. (b) Knochel, P.; Seebach, D. Synthesis 1982, 1017.