Reaction of 2,3-dihydro-1,5-benzothiazepines and phenylacetyl chloride in the presence of triethylamine: A new aspect on the formation mechanism of dihydro-1,3-oxazin-4-one derivatives

Chinese Journal of Chemistry

Volumn 22, Issue 9 SPEC.ISS., 2004, Pages 1012-1018

  Xu, Jia Xi ^a   Wang, Chao ^a   Zhang, Qi Han ^a  

^a PEKING UNIVERSITY   (China)

Author keywords

1,5 benzothiazepine; 2,2a,3,4 tetrahydro 1H azeto 2,1 d 1,5 benzothiazepin 1 one; 2,3 dihydrobenzothiazole; 4a,5 dihydro 1H,6H 1,3 oxazino 2,3 d 1,5 benzothiazepin 1 one; Cycloaddition; Mechanism

Indexed keywords

2,2A,3,4 TETRAHYDRO 2 PHENYL 1H AZETO[2,1 D][1,5]BENZOTHIAZEPIN 1 ONE DERIVATIVE; 2,3 DIHYDRO 1,3 OXAZIN 4 ONE DERIVATIVE; 2,3 DIHYDRO 1,5 BENZOTHIAZEPINE DERIVATIVE; 2,3 DIHYDRO 3 PHENYLACETYL 2 STYRYLBENZOTHIAZOLE DERIVATIVE; 3 BENZYL 4A,5 DIHYDRO 2 PHENYL 1H,6H[1,3]OXAZINO[2,3 D][1,5]BENZOTHIAZEPIN 1 ONE DERIVATIVE; 4A,5 DIHYDRO 1H,6H[1,3]OXAZINO[2,3 D][1,5]BENZOTHIAZEPIN 1 ONE DERIVATIVE; BENZOTHIAZEPINE DERIVATIVE; BETA LACTAM ANTIBIOTIC; CHLORINE DERIVATIVE; DIHYDRO 1,3 OXAZIN 4 ONE DERIVATIVE; OXAZINE DERIVATIVE; PHENYLACETYL CHLORIDE; TRIETHYLAMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLOADDITION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 7244234569     PISSN: 1001604X     EISSN: None     Source Type: Journal    
DOI: 10.1002/cjoc.20040220927     Document Type: Article

References (32)

1. Morin, R. B.; Gorman, M. Chemistry and Biology of β-Lactam Antibiotics, Vols. 1-3, Academic Press, New York, 1982.
2. Southgate, R.; Elson, S. In The Chemistry of Organic Natural Products, Vol. 47, Eds.: Herz, W.; Grisebach, H.; Kirby, G. W.; Tamm, C., Springer-Verlag, Wien, 1985.
3. Hegedus, L. S.; Imwinkelried, R.; Alarid-Sargent, M.; Dvorak, D.; Satoh, Y. J. Am. Chem. Soc. 1990, 112, 1109.
4. Xu, J. X.; Jin, S. Heteroat. Chem. 1999, 10, 35.
5. Xu, J. X.; Jin, S. Chin. Chem. Lett. 1992, 3, 181.
6. Xu, J. X.; Chen, L. B. Heteroat. Chem. 2000, 11, 158.
7. Xu, J. X.; Wu, H. T.; Jin, S. Chin. J. Chem. 1999, 17, 84.
8. Szollosy, A.; Kotovych, G.; Toth, C.; Levai, A. Can. J. Chem. 1988, 66, 279.
9. Pippich, S.; Bartsch, H.; Erker, T. J. Heterocycl. Chem. 1997, 34, 823.
10. Martinez, R.; Hernandez, P. E.; Angeles, E. J. Heterocycl. Chem. 1996, 33, 271.
11. Cores, E.; Martinez, R.; Ceballos, I. J. Heterocycl. Chem. 1989, 26, 119.
12. Xu, J. X.; Jiao, P.; Zuo, G.; Jin, S. Rapid Commun. Mass Spectrom. 2000, 14, 637.
13. Xu, J. X.; Zuo, G. Zhang, Q. H.; Chan, W. L. Heteroat. Chem. 2002, 13, 276.
14. Li, Y.; Du, C. Y.; Jin, S. Chem. J. Chin. Univ. 1999, 20, 1409 (in Chinese).
15. Huang, X.; Xu, J. X. Heteroat. Chem. 2003, 14, 564.
16. Toth, G.; Levai, A.; Balazs, B.; Simon, A. Liebigs Ann. 1997, 995.
17. (a) He, X. R.; Lin, X. Y.; He, M. Y.; Yu, Z. P.; Xu, J. X. J. Chin. Mass Spectrom. Soc. 1993, 14, 26 (in Chinese).
18. (b) Lin, X. Y.; He, X. R.; Yu, Z. P.; Xu, J. X. Acta Sci. Nat., Univ. Pekin. 1997, 33, 158 (in Chinese).
19. Maujean, A.; Chuche, J. Tetrahedron Lett. 1976, 2905.
20. Sohar, P.; Stajer, G; Pelczer, I.; Szabo, A. E.; Szunyog, J.; Bernath, G. Tetrahedron 1985, 41, 1721.
21. Arjona, O.; Csaky, A. G.; Murcia, M. C.; Plumet, J. Tetrahedron Lett. 2002, 6405.
22. Kato, T. Acc. Chem. Res. 1974, 7, 265.
23. Clemens, R. J. Chem. Rev. 1986, 86, 241.
24. Kato, T.; Yamamoto, Y. Chem. Pharm. Bull. 1967, 15, 1334.
25. Brand, W. T.; Dad, M. M. J. Org. Chem. 1991, 56, 6118.
26. Sauer, J. C. J. Am. Chem. Soc. 1947, 67, 2444.
27. Farnum, D. G.; Holmson, J. R.; Hess, R. E.; Marshall, T. B.; Webster, B. J. Am. Chem. Soc. 1965, 87, 5191.
28. Chen, L. B.; Zhang, Q. H.; Xu, J. X. Chin. J. Org. Chem. 2001, 21, 89 (in Chinese).
29. Chen, L. B.; Xu, J. X. Chin. J. Synth. Chem. 2000, 8, 231 (in Chinese).
30. Xu, J. X.; Zhang, Q. H.; Chen, L. B.; Chen, H. J. Chem. Soc., Perkin. Trans. 1 2001, 2266.
31. Xu, J. X.; Zhang, Q. H. Heteroat. Chem. 2001, 12, 630.
32. Xu, J. X.; Chen, L. B. Heteroat. Chem. 2002, 13, 165.