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Soluble polymer-supported synthesis of benzodiazepinones

Bioorganic & Medicinal Chemistry Letters, 2002
Soluble polymer-supported synthetic method provides a highly efficient route for the construction of biologically important 1,5-benzodiazepin-2-ones. A library of N-substituted benzodiazepinones can be readily assembled utilizing S(N)Ar reaction, reduction of nitro group and one-pot cyclization following N-alkylation as the key step in the synthesis ...
Cheng Yi, Wu, Chung Ming, Sun
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A new route to 1H-1,5-benzodiazepinones

Journal of the Chemical Society, Chemical Communications, 1981
Dimethyl allene-1,3-dicarboxylates react with o-phenylenediamine to give 1H-1, 5-benzodiazepinones and not benzimidazoles; the transient enamine intermediate shows preference for a 7-exo-trig ring closure.
John Ackroyd, Feodor Scheinmann
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ChemInform Abstract: Synthesis and Reaction of Dihydrofuro(3,4‐b)(1,5)benzodiazepinones and Dihydropyrrolo(3,4‐b)(1,5)benzodiazepinones.

ChemInform, 1987
AbstractThe benzodiazepinones (IV) are obtained by acylation and subsequent cyclization of the diamines (Ia) and (Ib).
K. MATSUO   +3 more
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Synthese und Struktur substituierter 1.5‐Benzodiazepinone‐(4)

Justus Liebigs Annalen der Chemie, 1966
AbstractPiperidondicarbonsäureester reagieren mit o‐Phenylendiamin unter Ringspaltung. Dabei entstehen, neben substituierten Benzimidazolen, 2‐Alkoxycarbonylmethylen‐2.3.4.5‐tetrahydro‐1H‐1.5‐benzodiazepinone‐(4) (z. B. 1, 2). Diese bilden sich auch bei direkter Kondensation von Acetondicarbonsäureestern mit o‐Phenylendiamin oder durch Cyclisierung von
Eberhard Müller   +2 more
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Auranthine, a new benzodiazepinone metabolite of Penicillium aurantiogriseum

Journal of the Chemical Society, Perkin Transactions 1, 1986
A novel metabolite, auranthine, has been isolated from sporing cultures of Penicillium aurantiogriseum and its structure, 6,7,7a,8-tetrahydroquinazolino[3′,2′:1,6]pyrido[2,3-b][1,4]benzodiazepine-9,16-dione comprising anthranilate and glutamine moieties, has been elucidated from spectral evidence and biosynthetic reasoning.
Stephanie E. Yeulet   +4 more
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ChemInform Abstract: N‐ARYL‐SUBSTITUIERTE 1,5‐BENZODIAZEPINONE

Chemischer Informationsdienst, 1972
AbstractDie 3‐(2‐Nitroanilino)‐propionsäuren (I) werden mit Zink und Phosphorsäure in Dioxan reduziert und zu den Benzodiazepinonen (II) kondensiert.
A. BAUER, K.‐H. WEBER, M. UNRUH
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Attempted synthesis of 2,4‐ and 1,3‐benzodiazepinones

Journal of Heterocyclic Chemistry, 1975
AbstractThe cyclodehydration reaction performed upon α‐acylamino carboxamides is known to constitute a facile synthetic approach to five‐membered heterocyclic systems. Attempts to prepare 2,4‐ and 1,3‐benzodiazepinone derivatives (VI, XIX) of potential C.N.S. Activity using such methods, proved unsuccessful. A new triazine system (X) which was prepared
Uri Golik, William Taub
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On substituent effect on the benzodiazepinone system

Computational and Theoretical Chemistry, 2012
Abstract Tautomerism, aromaticity, and electron density at ring critical points of substituted benzodiazepinones, composed of condensed 6- and 7-membered rings (7-substituted 1,3-dihydro-benzo[e][1,4]diazepin-2-ones), were studied at the B3LYP/6-31G ∗∗ level. We found that in the gas phase and in water, the N1H tautomers are more stable than the N4H
Grażyna Karpińska   +2 more
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Direct liquid chromatographic separation of benzodiazepinone enantiomers

Journal of Chromatography A, 1984
Abstract The enantiomers of 46 3-substituted 5-phenyl-1,3-dihydro(2H)1,4-benzodiazepin-2-ones, diazepam (Valium®) analogues, have been chromatographically separated on chiral stationary phases derived from (R)-phenyl-glycine or (S)-leucine. Both analytical and preparative scale separations have been effected.
William H. Pirkle, Athanasios Tsipouras
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