1,4-Diazepines: A Review on Synthesis, Reactions and Biological Significance.

BACKGROUND 1,4-Diazepines are two nitrogen containing seven membered heterocyclic compounds and associated with a wide range of biological activities. Due to its medicinal importance, scientists are actively involved in the synthesis, reactions and biological evaluation of 1,4-diazepines since number of decades. OBJECTIVE The primary purpose of this review is to discuss the synthetic schemes and reactivity of 1,4- diazepines. This article also describes biological aspects of 1,4-diazepine derivatives, that can be usefully exploited for the pharmaceutical sector. CONCLUSION This review summarizes the abundant literature on synthetic routes, chemical reactions and biological attributes of 1,4-diazepine derivatives. We concluded that 1,4-diazepines have significant importance due to their biological activities like antipsychotic, anxiolytic, anthelmintic, anticonvulsant, antibacterial, antifungal and anticancer. 1,4-diazepine derivatives with significant biological activities could be explored for potential use in the pharmaceutical industries.

[1]  G. Varvounis.  An Update on the Synthesis of Pyrrolo[1,4]benzodiazepines , 2016, Molecules.

[2]  S. Bansal,et al.  Recent development in [1,4]benzodiazepines as potent anticancer agents: a review. , 2014, Mini reviews in medicinal chemistry.

[3]  S. Saklani,et al.  Synthesis of the impurities during the manufacture of bulk drug midazolam and separation of these impurities by HPLC , 2013, Acta pharmaceutica.

[4]  N. Kaur,et al.  Application of chalcones in heterocycles synthesis: Synthesis of 2-(isoxazolo, pyrazolo and pyrimido) substituted analogues of 1,4-benzodiazepin-5-carboxamides linked through an oxyphenyl bridge , 2013, Journal of Chemical Sciences.

[5]  O. Hucke,et al.  Optimization of a 1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione series of HIV capsid assembly inhibitors 1: addressing configurational instability through scaffold modification. , 2013, Bioorganic & medicinal chemistry letters.

[6]  A. Abu Taha,et al.  Synthesis and Antibacterial Activity of Novel Curcumin Derivatives Containing Heterocyclic Moiety , 2013, Iranian journal of pharmaceutical research : IJPR.

[7]  M. Agrawal.  EXPEDIENT PROTOCOL FOR THE SYNTHESIS OF ISOXAZOLE, PYRAZOLE, PYRIMIDINE DERIVATIVES AND THEIR MEDICINAL IMPORTANCE , 2013 .

[8]  THEORETICAL STUDY OF 1, 4-DIAZEPINES SYNTHESIS: THE REACTION MECHANISM AND TAUTOMERISM IN GAS PHASE AND IN SOLUTION , 2013 .

[9]  Meenakshi Sharma,et al.  Exploration of Newer Possibilities to the Synthesis of Diazepine and Quinoline Carboxylic Acid Derivatives , 2013 .

[10]  Y. Joshi,et al.  Synthesis and Spectral Studies of Novel Diazepine Derivatives and Study in Specific Reference to Tautomerization , 2013 .

[11]  S. Dubey,et al.  Validation of Quetiapine Fumarate in Pharmaceutical Dosage by Reverse-Phase HPLC with Internal Standard Method , 2013 .

[12]  R. Singh,et al.  Rapid and Efficient Synthesis of 2,3-Dihydro-1H-1,5- Benzodiazepines Catalyzed by Chloroacetic Acid Screened among Various Aliphatic Acids under Solvent Free Conditions , 2013 .

[13]  Mohammad Norouzi,et al.  An Efficient and Green Protocol for the Synthesis of 1,5-benzodiazepine and Quinoxaline Derivatives Using Protic Pyridinium Ionic Liquid as a Catalyst , 2013 .

[14]  S. Abdel‐Hafez,et al.  Microwave-Assisted Synthesis of Benzodiazepine Derivatives: As Non-nucleoside Anti HIV Analogue , 2012 .

[15]  A. Messeguer,et al.  Synthesis of enantiomerically pure perhydro-1,4-diazepine-2,5-dione and 1,4-piperazine-2,5-dione derivatives exhibiting potent activity as apoptosis inhibitors. , 2012, Bioorganic & medicinal chemistry letters.

[16]  A. Shafiee,et al.  Synthesis of Novel 1,4-Benzodiazepine-3,5-dione Derivatives: Reaction of 2-Aminobenzamides under Bargellini Reaction Conditions , 2012 .

[17]  Q. Wang,et al.  Docking Analysis and Multidimensional Hybrid QSAR Model of 1,4-Benzodiazepine-2,5-Diones as HDM2 Antagonists , 2012, Iranian journal of pharmaceutical research : IJPR.

[18]  P. A. Tarakanov,et al.  Porphyrazines with annulated diazepine rings 4: Synthesis and properties of MgII tetradiazepinoporphyrazine carrying exocyclic styryl fragments , 2012 .

[19]  M. J. Ramaiah,et al.  Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates. , 2012, Bioorganic & medicinal chemistry letters.

[20]  G. Imanzadeh,et al.  Synthesis and conformational analysis of new derivatives of 7-chloro-1,3-dihydro-5-phenyl-2h-1,4-benzodiazepine-2-one , 2011, 1112.5533.

[21]  Sophie Houngninou-Molango,et al.  Design, synthesis and biological activity of original pyrazolo-pyrido-diazepine, -pyrazine and -oxazine dione derivatives as novel dual Nox4/Nox1 inhibitors. , 2011, Bioorganic & medicinal chemistry.

[22]  R. Kumar,et al.  Silica Sulfuric Acid as a Mild and Efficient Reagent for the Synthesis of 1,4-Diazepine and 1,5-Benzodiazepine Derivatives , 2011 .

[23]  J. Wietrzyk,et al.  Synthesis and antiproliferative activity in vitro of new pyrido[1,4-b]diazepine derivatives and imidazo[4,5-b]pyridine. , 2011, Acta poloniae pharmaceutica.

[24]  F. Fronczek,et al.  Synthesis of 2-amino-1,4-benzodiazepin-5-ones from 2-nitrobenzoic acid and α-aminonitriles , 2011 .

[25]  U. McDermott,et al.  Discovery of a benzo[e]pyrimido-[5,4-b][1,4]diazepin-6(11H)-one as a Potent and Selective Inhibitor of Big MAP Kinase 1 , 2011, ACS medicinal chemistry letters.

[26]  Guigen Li,et al.  [4+2+1] Domino cyclization in water for chemo- and regioselective synthesis of spiro-substituted benzo[b]furo[3,4-e][1,4]diazepine derivatives , 2011 .

[27]  D. Thurston,et al.  Synthesis of DNA-interactive pyrrolo[2,1-c][1,4]benzodiazepines (PBDs). , 1994, Chemical reviews.

[28]  B. Dawane,et al.  Polyethylene glycol (PEG-400): An efficient and recyclable reaction medium for the synthesis of novel 1; 5-benzodiazepines and their antimicrobial activity , 2011 .

[29]  C. Rabia,et al.  Synthesis of Substituted 1,4-Diazepines and 1,5-Benzodiazepines Using an Efficient Heteropolyacid-Catalyzed Procedure , 2010, Molecules.

[30]  K. Unverferth,et al.  Synthesis of disubstituted 1,4-diazepines with affinity to GABAA-receptor subtypes. , 2010, Die Pharmazie.

[31]  E. Domínguez,et al.  A versatile PIFA-mediated approach to structurally diverse pyrrolo(benzo)diazepines from linear alkynylamides , 2010 .

[32]  K. Shawakfeh,et al.  A facial synthesis of quinazolino[1,4]benzodiazepine alkaloids via reductive N-heterocyclization of N-(2-nitrobenzoyl)amides: total synthesis of asperlicin C, circumdatin H, and its analogues , 2010 .

[33]  V. A. Shcherbinin,et al.  Furan ring opening-pyrrole ring closure: a new synthetic route to aryl(heteroaryl)-annulated pyrrolo[1,2-a][1,4]diazepines. , 2010, Organic & biomolecular chemistry.

[34]  Y. Joshi,et al.  Synthesis, Spectral Studies and Biological Activity of Novel 1H‐1,4‐Diazepine Derivatives. , 2010 .

[35]  R. Butcher,et al.  5,7-Dimethyl-2,3-dihydro-1H-1,4-diazepin-4-ium picrate , 2010, Acta crystallographica. Section E, Structure reports online.

[36]  Yunkui Liu,et al.  Sodium tetrachloroaurate(III) dihydrate-catalyzed efficient synthesis of 1,5-benzodiazepine and quinoxaline derivatives , 2010, Journal of Zhejiang University SCIENCE B.

[37]  M. G. Landge,et al.  Solvent-Free one pot synthesis of benzo-[b]-1,4-diazepines using reusable sulfamic acid catalyst , 2009 .

[38]  R. Kumar,et al.  Synthesis, antimicrobial and antifungal activities of novel 1H-1,4-diazepines containing pyrazolopyrimidinone moiety , 2009 .

[39]  F. Melani,et al.  Tricyclic heteroaromatic systems. 5H-1,2,3-triazolo[5,1-c][1,4]benzodiazepine , 2009 .

[40]  J. N. Low,et al.  Bischler-Napieralski cyclocondensation in the synthesis of new 11H-pyrimido[4,5-b][1,4]benzodiazepines , 2008 .

[41]  Kamal M. El-Shaieb.  Condensation of 1-(Dicyanomethylene)acenaphthene-2-one with Aromatic Diamines , 2008 .

[42]  Veerababurao Kavala,et al.  Efficient TCT-catalyzed Synthesis of 1,5-Benzodiazepine Derivatives under Mild Conditions , 2008, Molecules.

[43]  Y. Gong,et al.  A Novel Solid-Phase Synthetic Method for 1,4-Benzodiazepine-2,5-dione Derivatives , 2008 .

[44]  S. Sen,et al.  Phosphonate-linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates: synthesis, DNA-binding affinity and cytotoxicity. , 2008, Bioorganic & medicinal chemistry.

[45]  Jeffrey Aubé,et al.  Three-component synthesis of 1,4-diazepin-5-ones and the construction of gamma-turn-like peptidomimetic libraries. , 2008, Journal of combinatorial chemistry.

[46]  A. Hatami,et al.  Facile and Efficient One‐Pot Protocol for Synthesis of 5‐Phenyl‐1,4‐benzodiazepine‐2‐one Derivatives , 2008 .

[47]  K. Bahrami,et al.  TCT as a Rapid and Efficient Catalyst for the Synthesis of 1,5-Benzodiazepines , 2008 .

[48]  N. Meanwell,et al.  1,4-Diazepines , 2008 .

[49]  K. Basavaraja,et al.  Synthesis of Benzofuro[3,2-e]-1,4-diazepines of Pharmacological Interest , 2008 .

[50]  A. Maleki,et al.  A Fast and Efficient Method for the Synthesis of 1,5-Benzodiazepine Derivatives Under Solvent-Free Conditions , 2007 .

[51]  J. Ilaš,et al.  1,4‐Diazepine‐2,5‐dione ring formation during solid phase synthesis of peptides containing aspartic acid β‐benzyl ester , 2007, Journal of peptide science : an official publication of the European Peptide Society.

[52]  S. Sen,et al.  1,2,4-benzothiadiazine linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates: synthesis, DNA-binding affinity and cytotoxicity. , 2007, Bioorganic & medicinal chemistry letters.

[53]  C. Bachmann,et al.  Design, synthesis and biological evaluation of 1,4-benzodiazepine-2,5-dione-based HDAC inhibitors. , 2007, Bioorganic & medicinal chemistry letters.

[54]  R. Giridhar,et al.  Current scenario of 1,4-diazepines as potent biomolecules--a mini review. , 2007, Mini reviews in medicinal chemistry.

[55]  N. Zanatta,et al.  The first synthesis of dihydro-3H-pyrido[2,3-b][1,4]diazepinols and a new alternative approach for diazepinone analogues , 2007 .

[56]  T. C. Jenkins,et al.  Synthesis of a novel C2-aryl pyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione library: effect of C2-aryl substitution on cytotoxicity and non-covalent DNA binding. , 2007, Bioorganic & medicinal chemistry.

[57]  A. V. Butin,et al.  A New Strategy for Pyrrolo[1,2-a][1,4]diazepine Structure Formation , 2007 .

[58]  Ramu Enugala,et al.  p-nitrobenzoic acid promoted synthesis of 1,5-benzodiazepine derivatives , 2007 .

[59]  R. Giridhar,et al.  Synthesis of novel substituted diaryl-1,4-diazepines , 2006 .

[60]  Tianbao Lu,et al.  Novel 1,4-benzodiazepine-2,5-diones as Hdm2 antagonists with improved cellular activity. , 2006, Bioorganic & medicinal chemistry letters.

[61]  Maxwell D Cummings,et al.  Enhanced pharmacokinetic properties of 1,4-benzodiazepine-2,5-dione antagonists of the HDM2-p53 protein-protein interaction through structure-based drug design. , 2006, Bioorganic & medicinal chemistry letters.

[62]  Tianbao Lu,et al.  Enantiomerically pure 1,4-benzodiazepine-2,5-diones as Hdm2 antagonists. , 2006, Bioorganic & medicinal chemistry letters.

[63]  .. M.A.Pasha,et al.  An Expeditious Synthesis of 1,5-Benzodiazepine Derivatives Catalysed by p-toluenesulfonic Acid , 2006 .

[64]  M. A. Pasha,et al.  Synthesis of 1,5-Benzodiazepine derivatives catalysed by zinc chloride , 2006 .

[65]  Sreelatha Nuvula,et al.  Ceric ammonium nitrate (CAN) promoted efficient synthesis of 1,5-benzodiazepine derivatives , 2006 .

[66]  B. V. Ashalatha,et al.  Synthesis of some new substituted triazolo [4,3-a][1,4] benzodiazepine derivatives as potent anticonvulsants. , 2006, European journal of medicinal chemistry.

[67]  Jeh-Jeng Wang,et al.  Design, synthesis, and biological evaluation of pyrrolo[2,1-c][1,4]benzodiazepine and indole conjugates as anticancer agents. , 2006, Journal of medicinal chemistry.

[68]  R. Begent,et al.  Synthesis and biological evaluation of novel pyrrolo[2,1-c][1,4]benzodiazepine prodrugs for use in antibody-directed enzyme prodrug therapy. , 2006, Bioorganic & medicinal chemistry letters.

[69]  A. Failli,et al.  (4-Substituted-phenyl)-(5H-10,11-dihydro-pyrrolo [2,1-c][1,4] benzodiazepin-10-yl)-methanone derivatives as vasopressin receptor modulators. , 2005, Bioorganic & medicinal chemistry letters.

[70]  P. Taylor,et al.  Pyrrolobenzodiazepine dimers: novel sequence-selective, DNA-interactive, cross-linking agents with activity against Gram-positive bacteria. , 2005, The Journal of antimicrobial chemotherapy.

[71]  B. M. Reddy,et al.  Sulfated zirconia as an efficient catalyst for organic synthesis and transformation reactions , 2005 .

[72]  L. Meerpoel,et al.  Pyrrolo[1,2-a][1,4]benzodiazepine: a novel class of non-azole anti-dermatophyte anti-fungal agents. , 2005, Bioorganic & medicinal chemistry letters.

[73]  J. Lown,,et al.  Design, synthesis and in vitro cytotoxic studies of novel bis-pyrrolo[2,1][1,4] benzodiazepine-pyrrole and imidazole polyamide conjugates. , 2005, European journal of medicinal chemistry.

[74]  X. Pannecoucke,et al.  An Efficient Asymmetric Synthesis of 2‐Substituted 1,4‐Benzodiazepin‐3‐one as a Potential Molecular Scaffold , 2005 .

[75]  G. Lushington,et al.  Modular Synthesis of Cyclic Peptidomimetics Inspired by γ-Turns† , 2005 .

[76]  R. Gibbs,et al.  Scandium(III) triflate as an efficient and reusable catalyst for synthesis of 1,5-benzodiazepine derivatives , 2005 .

[77]  J. Yadav,et al.  InCI3-catalyzed stereoselective synthesis of optically pure 1,5-benzodiazepines , 2005 .

[78]  K. Nagaiah,et al.  Indium(III) Bromide: A Novel and Efficient Reagent for the Rapid Synthesis of 1,5-Benzodiazepines under Solvent-Free Conditions , 2005 .

[79]  Maxwell D Cummings,et al.  1,4-Benzodiazepine-2,5-diones as small molecule antagonists of the HDM2-p53 interaction: discovery and SAR. , 2005, Bioorganic & medicinal chemistry letters.

[80]  S. Marcaccini,et al.  A facile synthesis of 1,4-benzodiazepine derivatives via Ugi four-component condensation , 2005 .

[81]  J. Bergman,et al.  Synthesis of 1,4-benzodiazepine-3,5-diones. , 2004, The Journal of organic chemistry.

[82]  J. Yadav,et al.  A New, Efficient and Environmentally Benign Protocol for the Synthesis of 1,5-Benzodiazepines using Cerium(III) Chloride/Sodium Iodide Supported on Silica Gel† , 2004 .

[83]  G. Fox,et al.  D‐Amino Acid Homopiperazine Amides: Discovery of A‐320436, a Potent and Selective Non‐Imidazole Histamine H3‐Receptor Antagonist , 2004 .

[84]  Y. Chapleur,et al.  Anomeric spiroannelated 1,4-diazepine 2,5-diones from furano exo-glycals: towards a new class of spironucleosides , 2004 .

[85]  H. Okabe,et al.  Trypanocidal constituents in plants 4. Withanolides from the aerial parts of Physalis angulata. , 2004, Biological & pharmaceutical bulletin.

[86]  Sven H. Hausner,et al.  Novel 4-Aroyl-3-alkoxy-2(5H)-furanones as Precursors for the Preparation of Furo[3,4-b][1,4]-diazepine Ring System‡ , 2003, Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry.

[87]  M. Preobrazhenskaya,et al.  Synthesis of 6H-pyrrolo[3',4':2,3][1,4]diazepino[6,7,1-hi]indole-8,10(7H,9H)-diones using 3-bromo-4-(indol-1-yl)maleimide scaffold. , 2003, Organic & biomolecular chemistry.

[88]  R. Rajagopal,et al.  Room temperature ionic liquid promoted synthesis of 1,5-benzodiazepine derivatives under ambient conditions , 2003 .

[89]  Hiroshi Harada,et al.  Synthesis and structure-affinity relationships of novel N-(1-ethyl-4-methylhexahydro-1,4-diazepin-6-yl)pyridine-3-carboxamides with potent serotonin 5-HT3 and dopamine D2 receptor antagonistic activity. , 2003, Journal of medicinal chemistry.

[90]  F. Ercole,et al.  Synthesis of tetrahydro-1,4-benzodiazepine-2-ones on hydrophilic polyamide SynPhase lanterns. , 2003, Journal of combinatorial chemistry.

[91]  Synthesis and DNA strand breakage activity of some 1,4-diazepines. , 2003, Chemical & pharmaceutical bulletin.

[92]  J. Yadav,et al.  Amberlyst-15®: a novel and recyclable reagent for the synthesis of 1,5-benzodiazepines in ionic liquids , 2002 .

[93]  H. Duddeck,et al.  Synthesis of 1,4-Diazepine Nucleosides , 2002 .

[94]  J. Stephanidou-Stephanatou,et al.  An efficient method for the synthesis of 1,5-benzodiazepine derivatives under microwave irradiation without solvent , 2002 .

[95]  A. Loupy,et al.  Synthesis of aromatic and heteroaromatic annelated (1,4)diazepines , 2001 .

[96]  S. Salamone.  Benzodiazepines and GHB , 2001 .

[97]  B. Kaboudin,et al.  Alumina/Phosphorus Pentoxide (APP) as an Efficient Reagent for the Synthesis of 1,5-Benzodiazepines under Microwave Irradiation , 2001 .

[98]  M. Curini,et al.  Ytterbium triflate promoted synthesis of 1,5-benzodiazepine derivatives , 2001 .

[99]  M. Balakrishna,et al.  A simple and new method for the synthesis of 1,5-benzodiazepine derivatives on a solid surface , 2001 .

[100]  E. Mikiciuk-Olasik,et al.  New Mitoguazone Analogues with Anticancer Activity , 1999 .

[101]  D. Jung,et al.  Synthesis Of 1,5-Benzodiazepine Derivatives , 1999 .

[102]  R. Martínez,et al.  2-Aryl-7,7-dimethyl-5,6,7,8-tetrahydrothieno[3,2-c]azepin-4-ones from 5,5-dimethyl-1,3-cyclohexanedione , 1999 .

[103]  G. Primofiore,et al.  Synthesis of purinobenzodiazepine and purinobenzotriazocine derivatives, two new heterocyclic ring systems , 1999 .

[104]  J. Skotnicki,et al.  The synthesis and biological activity of a novel series of diazepine MMP inhibitors. , 1998, Bioorganic & medicinal chemistry letters.

[105]  C. Martini,et al.  1,2,3-Triazolo[1,5-a][1,4]- and 1,2,3-triazolo[1,5-a]-[1,5]benzodiazepine derivatives: synthesis and benzodiazepine receptor binding. , 1998, Farmaco.

[106]  G. Tóth,et al.  Conformational analysis of 2,3-dihydro-2,2-dimethyl-1,4-benzoxazepines and their 1,5-isomers , 1997 .

[107]  S. Kato,et al.  Efficient synthesis of (6R)-6-amino-1-methyl-4-(3-methylbenzyl)hexahydro-1H-1,4-diazepine from methyl (2R)- and (2S)-1-benzyloxycarbonylaziridine-2-carboxylates , 1997 .

[108]  C. Monneret,et al.  Imidazo[1,5-g][1,4]diazepines, TIBO analogues lacking the phenyl ring: synthesis and evaluation as anti-HIV agents. , 1996 .

[109]  Structural optimization of 4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f]-[1,2,4]triazolo[4,3-a][1,4]diazepines as antagonists for platelet activating factor: pharmacological contribution of substituents at the 2- and 6-positions of a condensed ring system , 1996 .

[110]  D. Thurston,et al.  SYNTHESIS OF DNA-INTERACTIVE PYRROLO2,1-C1,4BENZODIAZEPINES , 1994 .

[111]  A. Mai,et al.  Pyrrolobenzodiazepines and related systems. 2. Synthesis and biological properties of isonoraptazepine derivatives. , 1992, Journal of medicinal chemistry.

[112]  S. Nandan,et al.  Synthesis of the liposidomycin diazepanone , 1992 .

[113]  A. Mai,et al.  Pyrrolobenzodiazepine and related systems. I. Synthesis and pharmacological evaluation of new 5,6-dihydro-4H-pyrrolo[1,2-a][1,4]benzodiazepine derivatives. , 1990, Farmaco.

[114]  A. Mai,et al.  [5-Aroyl-5,6-dihydro-4H-pyrrolo[1,2-a][1,4]benzodiazepin-4-carboxylic acids: synthesis and analgesic and neurobehavioral activity]. , 1989, Farmaco.

[115]  E. J. Glamkowski,et al.  Tetracyclic benzodiazepines. 4. Synthesis of the novel benzo[c]pyrrolo[1,2,3-ef][1,5]benzodiazepine ring system, and derivatives with potential antipsychotic activity , 1987 .

[116]  M. Artico,et al.  Benzodiazepines with both sedative and analgesic activities , 1987 .

[117]  R. Contreras,et al.  New Synthesis of Dihydro- and Tetrahydro-1,5-benzodiazepines by Reductive Condensation of o-Phenylenediamine and Ketones in the Presence of Sodium Borohydride , 1986 .

[118]  S. Paul,et al.  Pharmacological and neurochemical properties of 1,4-diazepines with two annelated heterocycles ('hetrazepines'). , 1985, European journal of pharmacology.

[119]  K. Hideg,et al.  FURTHER STUDIES OF THE MIXTURE OBTAINED FROM REACTIONS BETWEEN CONJUGATED ENONES AND ETHYLENEDIAMINE, AND FROM CONJUGATED ENONES AND 1-AMINOPROPANE , 1981 .

[120]  M. Gates.  New synthesis of diazepam , 1980 .

[121]  T. Mori,et al.  Diazepines. 5. Synthesis and biological action of 6-phenyl-4H-pyrrolo[1,2-a][1,4]benzodiazepines. , 1978, Journal of medicinal chemistry.

[122]  A. Walser,et al.  Quinazolines and 1,4-benzodiazepines LXXXII. Reaction of 2-hydrazino-benzodiazepines with 1,3-diearbonyl compounds† , 1978 .

[123]  H. Suschitzky,et al.  Syntheses of heterocyclic compounds. Part XXIX. Substituted 2,3-dihydro-1H-1,5-benzodiazepines , 1974 .

[124]  T. L. Lemke,et al.  The synthesis of oxazolo- and oxazino[3,2-d] [1,4]benzodiazepinones , 1971 .

[125]  A. Karr,et al.  Isolation and characterization of anthramycin, a new antitumor antibiotic. , 1965, Journal of the American Chemical Society.