Rearrangement of pyrrolo[2,1-c][1,4]benzodiazepines into cyclopenta[b][1,4]benzodiazepines under microwave or conventional heating conditions

Tetrahedron Letters

Volumn 38, Issue 13, 1997, Pages 2271-2274

  Gillard, Alain Claude ^a   Fabis, Frédéric ^a   Jolivet Fouchet, Sandrine ^a   Rault, Sylvain ^a  

^a UNIVERSITÉ DE CAEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BENZODIAZEPINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; HEATING; IN VITRO STUDY; ISOMERISM; MASS SPECTROMETRY; MICROWAVE COOKING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031592588     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00359-6     Document Type: Article

References (8)

1. 1. Rault, S.; Gillard, A.C.; Foloppe, M.P.; Robba, M. Tetrahedron Lett., 1995, 36, 6673-6674.
2. 2. Kamal, A.; Thurston, D.E. Tetrahedron Lett., 1989, 30, 6221-6222.
3. 1H NMR). By washing with cold methanol, 1g of 7 as insoluble material was isolated. After evaporation of the methanol, 0.3g of 3 crystallized from ether.
4. 4. Carey, F.A.; Giuliano, R.M. J. Org. Chem., 1981, 46, 1366-1371.
5. 5. Gillard, A.C.; Alkhader, M.; Rault, S. Heterocyclic Commun., 1996, 2, 409-414.
6. 6. Thurston, D.E.; Bose, D.S. Chem. Reviews, 1994, 94, 433-467.
7. 8 apparatus. After elimination of phosphoryl chloride under reduced pressure, the residue was taken up in water, basified (pH 11) with a 32% ammonia solution and extracted with diethyl ether. The organic layer was evaporated to give a mixture of 11 and 12. By washing with cold methanol, a yellow solid was isolated. By crystallization from ethanol, 2.6g (40%) of 11 was obtained. After evaporation of the methanol, 0.4g (7%) of 12 crystallized from ether.
8. 8. Rault, S.; Derobert, M. Eur. Pat. Appl. 0595084 A1. 1993. * Caution! Compounds 6, 8 and 11 are severe irritants and must be handled only with gloves under a chemical fume hood.