Synthesis of New (4‐Acetonylidene‐2,6,8,9‐tetramethyl‐7H‐imidazo[1,5,4‐e,f][1,5]benzodiazepine) Derivatives

References

• Shabunova , V. P. , Sergeeva , Z. F. , Akhvlediani , R. N. , Vasilev , A. M. , Gorelova , N. V. and Suvorov , N. N. 1978 . Synthesis of 3H‐pyrrolo[2,3‐h]quinolines and its derivatives . Khim. Farm. Zh. , 12 ( 6 ) : 53
   Google Scholar
• Paulens , R. , Andries , K. , Desmyter , J. , Schols , D. , Kukla , M. J. , Breslin , H. J. , Raeymaeckers , A. , Gelder , J. V. , Woestenborghs , R. , Heykants , J. , Schellekens , K. , Janssen , M. A. C. , De Clerq , E. and Janssen , P. A. J. 1990 . Potent and selective inhibition of HIV‐1 replication in vitro by a novel series of TIBO derivatives . Nature , 343 : 470
   PubMedGoogle Scholar
• Parker , K. A. and Coburn , C. A. 1991 . A four‐step synthesis of TIBO R82150 . J. Org. Chem. , 56 : 4600
   Google Scholar
• Kukla , M. J. , Breslin , H. J. , Paulens , R. , Fedde , C. L. and Miranda , M. 1991 . J. Med. Chem. , 34 ( 2 ) : 746
   PubMedGoogle Scholar
• Parker , K. A. and Coburn , C. A. 1992 . Regioselectivity in intramolecular nucleophilic aromatic substitution: synthesis of the potent HIV‐1 8‐haloTIBO analogues . J. Org. Chem. , 57 ( 1 ) : 97
   Google Scholar
• Caldwell , G. W. , Gauthier , A. D. , Leo , G. C. and Kukla , M. J. 1993 . Conformational analysis of the reverse transcriptase inhibitor (+)‐(S)‐4,5,6,7‐tetrahydroimidazo‐9‐chloro‐5‐methyl‐6‐(3‐methyl‐2‐butenyl)imidazo[4,5,1‐jk][1,4]‐benzodiazepin‐2(1H)‐thione (TIBO; R82913) . J. Med. Chem. , 34 ( 13 ) : 2063
   Google Scholar
• Ho , W. , Kukla , M. J. , Breslin , H. J. , Ludovici , D. W. and Grous , P. P. 1995 . Synthesis and anti‐HIV‐1 activity of 4,5,6,7‐tetrahydro‐5‐methylimidazo[4,5,1‐j,k]benzodiazepine‐2(1H)‐one (TIBO) derivatives . J. Med. Chem. , 38 ( 5 ) : 794
   PubMedGoogle Scholar
• Mohrbacher , R. 1995 . Synthesis and anti‐HIV‐1 activity of 4,5,6,7‐tetrahydro‐5‐methyl‐imidazo[4,5,1‐j,k][1,4]benzodiazepin‐2(1H)‐one (TIBO) derivatives . J. Med. Chem. , 5 ( 5 ) : 771
   Google Scholar
• Benchidmi , M. , El Kihel , A. , Essassi , E. M. , Knouzi , N. , Toupet , L. and Danion‐Bougot , R. 1995 . Carrié, R. Nitration de benzimidazoles substitués . Bull. Soc. Chim. Belg. , 104 : 605
   Google Scholar
• El Kihel , A. , Benchidmi , M. , Essassi , E. M. and Danion‐Bougot , R. 1999 . Halogenation of substituted benzimidazoles, nitration of the resulting halobenzimidazoles . Synth. Commun. , 29 ( 3 ) : 387
   Google Scholar
• El Kihel , A. , Benchidmi , M. , Essassi , E. M. , Bauchat , P. and Danion‐Bougot , R. 1999 . Reaction of aminobenzimidazoles with 4‐hydroxy‐6‐methyl‐2‐pyrone and 4‐hydroxycoumarine . Synth. Commun. , 29 ( 14 ) : 2435
   Google Scholar
• Benchidmi , M. and Essassi , E. M. 1987 . Synthèse et étude de RMN1H en présence de l'Eu(fod)3 des pyrazolo [1,5,4‐ef] benzodiazépine‐1,5 ones‐6 . Bull. Soc. Chim. Belg. , 96 ( 4 ) : 399
   Google Scholar
• Benchidmi , M. and Essassi , E. M. 1988 . Nouvelle synthèse diastéréosélective des pyrazolo[1,5,4‐e,f]benzodiazépines . Tetrahedron Lett. , 29 ( 34 ) : 4291
   Google Scholar
• Benchidmi , M. , Essassi , E. M. and Ibn mansour , A. 1992 . Synthèse de nouveaux systèmes hétérocycliques: Les pyrazolo [1,5,4‐ef] trizolo [3,4‐a] [1,5] benzodiazépines . Bull. Soc. Chim. Belg. , 101 ( 12 ) : 995
   Google Scholar
• Rakib , E. M. , Benchidmi , M. , Essassi , E. M. , Kandri Rodi , Y. , Bellan , J. and Lopez , L. 1996 . Halogénation des pyrazolo[1,5,4‐ef] [1,5] benzodiazépinones avec les N‐halogéno‐succinimides . Bull. Soc. Chim. Belg. , 105 ( 6 ) : 345
   Google Scholar
• El Ouar , M. , Knouzi , N. and Hamelin , J. 1998 . Reaction of ethyl 7‐minoindole‐2‐carboxylate with β‐diketone and β‐oxoester compounds . J. Chem. Res. Synop. , : 92
   Google Scholar
• Marcos , A. , Pedregal , C. and Avendano , C. 1991 . Reactivity of 4(7)‐aminobenzimidazole as a bidentate nucleophile . Tetrahedron , 47 ( 35 ) : 7459
   Google Scholar
• Bogatskii , A. V. , Ivanova , R. Yu. , Andronati , S. A. and Zhiline , Z. I. 1981 . Synthesis of 4,5‐dihydropyrrolo[1,2,3‐e,f][1,5]benzodiazepin‐6(7H)‐ones . Khim. Geterotsikl. Soedin. , : 505
   Google Scholar
• Akhvlediani , R. N. , Mikheeva , S. V. , Khachidze , M. M. , Sazonov , S. K. and Suvorov , N. N. 1980 . Synthesis of 5,7‐dimethyl‐1H‐pyrrolo[2,3‐g]quinolines . Zh. Org. Khim. , 16 ( 6 ) : 1338
   Google Scholar
• El Abbassi , M. , Essassi , E. M. and Fifani , J. 1987 . Nouvelle synthese des benzodiazepines‐1,5 à partir de la γ‐pyrone . Tetrahedron Lett. , : 1389
   Google Scholar
• El Abbassi , M. , Essassi , E. M. and Fifani , J. 1997 . Synthèse de nouvelles 4‐acetonylidene‐1,5‐benzodiazépine‐2‐ones . Bull. Soc. Chim. Belg. , 106 : 205
   Google Scholar
• El Abbassi , M. , Djerrari , B. , Essassi , E. M. and Fifani , J. 1989 . L'acide dehydracetique, precurseur de synthese de benzodiazepines . Tetrahedron Lett. , : 7069
   Google Scholar