Synthesis and separation of new dibenz[b,d]azonine atropisomers

Synthetic Communications

Volumn 27, Issue 9, 1997, Pages 1501-1507

  Pascal, Cécile ^a   Guéritte Voegelein, Françoise ^a   Thal, Claude ^a   Guénard, Daniel ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

DIBENZ[B,D]AZONINE DERIVATIVE; HETEROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; THERMODYNAMICS;

EID: 1842301772     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919708006086     Document Type: Article

References (10)

1. This work is part of a research program carried out in collaboration with the team of Prof. G. Queguiner (Laboratoire de Chimie Organique Fine et Hétérocyclique, INSA, Mont Saint Aignan). The purpose of this program is the synthesis of new biaryl compounds of potential biological interest.
2. Thoison, O., Guénard, D. Sévenet, T., Kan-Fan, C., Quirion, J-C., Husson, H-P., Deverre, J-R., Chan, K.C. and Potier, P. C.R.Acad.Sci.Ser 2 1987, 304, 157.
3. David, B., Sévenet, T., Morgat, M., Guénard, D., Moisand, A., Tollon, Y., Thoison, O. and Wright, M. Cell Motility and the Cytoskeleton 1994, 28, 317.
4. Alazard, JP., Millet-Paillusson, C., Guénard, D. and Thal, C. Bull. Soc. Chim. Fr. 1996, 133, 251.
5. Soufyane, M. Ph.D.Dissertation 1993, Université Reims, Champagne-Ardenne, France.
6. Gillis, R.G. and Porter, Q.N. Aust J. Chem. 1990, 43, 203.
7. Tamaru, Y., Ochiai, H., Nakamura, T., Tsubaki, K. and Yoshida, Z. Tetrahedron Lett. 1985, 26, 5559.
8. Chan, T.H., Brook, M.A. and Chaly, T. Synthesis 1983, 203.
9. The protection with ethylene glycol and trimethylsilyl chloride led also to a transesterification reaction leading to 2-hydroxyethyl and 2-chloroethyl esters with a yield of 28 and 13%. These two esters are hydrolyzed in the same conditions that ethyl ester 11 to give quantitatively the nitro-acid 12.
10. Hall D.M.; Harris, M.M. J.Chem.Soc. 1960, 490.