Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...
Patent
1994-08-08
1995-11-14
Shah, Mukund J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Unsubstituted hydrocarbyl chain between the ring and the -c-...
540569, 540574, C07D24320, C07D24316
Patent
active
054667992
ABSTRACT:
A general method is provided for the synthesis of substituted 2,3-dihydro-5-phenyl-1H-1,4-benzodiazepines by the reaction of bis-trifiated-2,5-dihydroxy benzophenones with 1,2-bisaminoethanes, followed by displacement of the 7-trifloxy group.
REFERENCES:
patent: 3109843 (1963-11-01), Reeder et al.
patent: 3136815 (1964-06-01), Reeder et al.
patent: 3313815 (1967-04-01), Wolfe et al.
patent: 3371085 (1968-02-01), Reeder et al.
patent: 4335054 (1982-06-01), Blaser et al.
patent: 5089273 (1992-02-01), Rinehart et al.
patent: 5256663 (1993-10-01), Rinehart et al.
Farina, V. et al. "Palladium Catalysis in Cephalosporin Chemistry: General Methodology for the Syntheis of Cephem Side Chains". J. Org. Chem. 55, 5833-5847 (1990).
Wickham, P. P. et al. "Benzyne Generation from Aryl Triflates." J. Org. Chem. 56, 2045-2050 (1991).
Katmizky, A. R. et al. Handbook of Heterocyclic Chemistry (Pergamon Press, New York), p. 476 (1985).
Echavarren, A. M. et al. "Palladium-Catalyzed Coupling of Aryl Triflates with Organostannemes." J. Am. Chem. Soc. 109, 5478-5486 (1987).
Dolle, R. E. et al., "Palladium Catalyzed Alkoxycarbonylation of Phenols to Benzoate Esters." J. Chem. Soc., Chem. Commun. (12), 904-905 (1987).
G. T. Crisp et al., "Palladium-Catalyzed Carbonylative Coupling of Vinyl Triflates with Organostannaes. A Total Synthesis of (.+-.).sup.9(12) -Capnellene", J. Am. Chem. Soc., 106, 7500-7506 (1984)***.
A. M. Felix et al., "Quinazolines and 1,4-Benzodiazepines. SLIII (1). Oxidations with Ruthenium Tetroxide", J. Het. Chem., 5, 731-734 (Oct. 1968).
M. Gates, "New Synthesis of Diazepam", J. Org. Chem., 45, 1675-1681 (1980).
M. Gerecke, "Chemical Structure and Properties of Midazolam Compared with other Benzodiazepines", Brit. J. Clin. Pharmacol., 16, 11S-16S (1983).
T. A. Hamor et al., "The Benzodiazepines"]in Progress in Med. Chem.--vol. 20; G. P. Ellis et al., Eds.; Elsevier Science Publishers: Amsterdam; pp. 157-223 (1983).
M. Ishikura et al., "New Synthesis of Diazepam and the Related 1,4-Benzodiazepines by means of Palladium-Catalyzed Carbonylation", J. Org. Chem., 47, 2456-2461 (1982).
G. A. Kraus et al., "Quinone Photochemistry. A General Synthesis of Acylhydroquinones", J. Org. Chem., 57, 3256-3257 (1992).
J. E. McMurry et al., "A New Method of Olefin Synthesis. Coupling of Lithium Dialkylcuprates with Enol Triflates", Tetrahedron Letters, 21, 4313-4316 (1980).
J. E. McMurry et al., "A Method for the Regiospecific Synthesis of Enol Triflates by Enolate Trapping", Tetrahedron Letters, 24, 979-982 (1983).
W. Milkowski et al., "1,4-Benzodiazepines and 1,5-benzodiazocines. VII. Synthesis and biological activity", Eur. J. Med. Chem.--Chim. Ther., 20, 345-358 (1985).
W. J. Scott et al., "Palladium-Catalyzed Coupling of Vinyl Triflates with Organostannanes. A Short Synthesis of Pleraplysillin-1", J. Am. Chem. Soc., 106, 4630-4632 (1984).
L. H. Sternbach et al., "Quinazolines and 1,4-Benzodiazepines. IV. Tranformations of 7-Chloro-2-methylamino-5-phenyl-3H-1,4-benzodiazepine 4-Oxide", J. Org. Chem., 26, 4936-4941 (Dec. 1961).
L. H. Sternbach et al., "Quinazolines and Benzodiazepines. XV. 7-Nitro-and 7-Trifluoromethyl-2,3-dihydro-5-phenyl-1H-1,4-1,4-benzodiazepines and Their Tranformations", J. Org. Chem., 28, 3013-3016 (Nov. 1963).
Iowa State University & Research Foundation, Inc.
Shah Mukund J.
Wong King L.
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