Synthesis of 8-substituted 5H,9H-6-oxa-7-azabenzocyclononene- 10,11- dione- 11-O-methyloximes, a new [1,2]-oxazonine ring system

Tetrahedron Letters

Volumn 41, Issue 9, 2000, Pages 1381-1384

  Pascual, Alfons ^a   Ziegler, Hugo ^a   Trah, Stephan ^a   Ertl, Peter ^a   Winkler, Tammo ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

Carbanions; Cyclic ketones; Cyclisation; Deprotonation; Oximes; Substitution

Indexed keywords

KETONE DERIVATIVE; OXIME DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON TRANSPORT; REACTION ANALYSIS; SYNTHESIS;

EID: 0034716502     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)01076-5     Document Type: Article

References (9)

1. Presented in part at the 17th International Congress of Heterocyclic Chemistry, Vienna University of Technology, August 1-6, 1999.
2. Farooq, S.; Trah, S.; Ziegler, H.; Zurflüh, R.; Pascual, A.; Szczepanski, H.; Hall, R. G. (Novartis). World Pat. Appl. WO 97/20809, 1997; Ziegler, H.; Trah, S.; Zurflüh, R.; Farooq, S. (Ciba-Geigy). World Pat. Appl. WO 95/18789, 1995.
3. Farooq, S.; Trah, S.; Ziegler, H.; Zurflüh, R.; Pascual, A.; Szczepanski, H.; Hall, R. G. (Novartis). World Pat. Appl. WO 97/20809, 1997; Ziegler, H.; Trah, S.; Zurflüh, R.; Farooq, S. (Ciba-Geigy). World Pat. Appl. WO 95/18789, 1995.
4. 3): see Fig. 2.
5. Livingston, M. J.; Chick, M. F.; Shealy, E. O.; Beam, C. F. J. Heterocycl. Chem. 1982, 19, 215.
6. 3): see Fig. 2. The second fraction from the filtration contains the acid 5 (2.00 g, 45%).
7. McClure, K. F.; Benbow, J. W.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 8185; Benbow, J. W.; McClure, K. F.; Danishefsky, S. J. Am. Chem. Soc. 1993, 113, 12 305.
8. McClure, K. F.; Benbow, J. W.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1991, 113, 8185; Benbow, J. W.; McClure, K. F.; Danishefsky, S. J. Am. Chem. Soc. 1993, 113, 12 305.
9. Jackman, L. M.; Sternhell, S. Application of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry; Pergamon, Oxford, 2nd ed., 1969, p. 88.