A new access to isoindolo[2,1-b] [2,4]benzodiazepines through an N-acyliminium ion - Amide cyclization

Tetrahedron Letters

Volumn 38, Issue 17, 1997, Pages 2985-2988

  Pigeon, Pascal ^a   Decroix, Bernard ^a  

^a UNIVERSITÉ DU HAVRE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BENZODIAZEPINE DERIVATIVE; ISOINDOLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS;

EID: 0030936555     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00539-X     Document Type: Article

References (16)

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2. Kamel, A.; Reddy, B.S.P.; Reddy, B.S.N. Tetrahedron Lett., 1996, 37, 6803-6806.
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10. Speckamp, W.N.; Hiemstra, H., Tetrahedron, 1985, 41, 4367-4416.
11. Pigeon, P. Ph.D. Dissertation, University of Le Havre, 1996.
12. Pigeon, P.; Decroix, B. Bull. Soc. Chim. Fr., 1997, in press.
13. The hydroxylactam-acid 5 (2.83 g, 10 mmol) and thionyl chloride (2 ml, 27 mmol) were refluxed in dry dichloromethane during one hour. The solution was cooled, then water (approx. 5 ml) was added. After strong stirring for 10 minutes, concentrated ammonia (approx. 20 ml for 11a) or 30% aqueous methylamine (approx. 20 ml for 11b) or pure butylamine (1 ml for 11c) was added. The mixture was stirred for 30 minutes then was poured in 10% aqueous sodium hydroxide. The organic layer was washed successively with 10% hydrochloric acid, saturated sodium hydrogen carbonate, water then was dried and concentrated. The residue was heated in toluene to reflux (Dean-Stark apparatus) with a catalytic amount of p-toluenesulfonic acid for two days. After cooling, the solution was washed with saturated sodium hydrogen carbonate then with water and was dried and concentrated. Recrystallization of the solid (chloroform for 11a, ethanol for 11b,c) furnished the corresponding diazepines.
14. 2), 66.2 (CH), 122.6 (CH), 124.5 (CH), 128.7 (CH), 129.5 (2CH), 129.8 (CH), 131.9 (2CH), 132.4 (C), 132.9 (C), 135.9 (C), 140.1 (C), 165.1 (CO), 170.6 (CO).
15. 2), 70.9 (CH), 124.1 (CH), 124.2 (CH), 129.0 (CH), 129.1 (CH), 129.8 (CH), 130.2 (CH), 131.9 (CH), 132.0 (C), 132.1 (CH), 133.8 (C), 135.9 (C), 137.9 (C), 165.2 (CO), 171.4 (CO).
16. 2), 71.0 (CH), 124.0 (CH), 124.4 (CH), 128.8 (CH), 129.0 (CH), 129.6 (CH), 130.1 (CH), 131.6 (CH), 131.8 (CH+C), 134.0 (C), 136.1 (C), 137.6 (C), 164.7 (CO), 170.9 (CO).