SYNTHETIC UTILITIES OF O-PHENYLENEDIAMINES : SYNTHETIC APPROACHES FOR BENZIMIDAZOLES, QUINOXALINES AND BENZO〔1,5〕DIAZEPINES

This review represents the methods developed for the synthesis of benzimidazoles, quinoxalines and benzo(1,5)diazepines from the condensation of o-phenylenediamines with a variety of electrophilic reagents. Abstract Published data over the last years on the methods of synthesis and biological applications of azolylthiazoles are reviewed here for the first time till 2011. The review was classified according to the type of azole ring linked to thiazole. Abstract A new 1,3-benzoxazine nuclei-based fluorescent system is presented. The photophysical aspects are briefly discussed. The results suggested that the presence of oxazinic methylenes is necessary for fluorescence to be present. Abstract An efficient and mild procedure for the decarboxylative cyanomethyl esterification of arylmalonic acids has been developed. The reaction can be performed at room temperature by using chloroacetonitrile and 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU) in toluene, and the desired arylacetic acid cyanomethyl esters are obtained in high yields within a short period of time.

[1]  Chen Zhang,et al.  Gold-catalyzed oxidation of arylallenes: Synthesis of quinoxalines and benzimidazoles , 2011, Beilstein journal of organic chemistry.

[2]  Khadijeh Soleimani,et al.  SYNTHESIS OF 1,2-DISUBSTITUTED BENZIMIDAZOLES AND 2-SUBSTITUTED BENZOTHIAZOLES CATALYZED BY HCl-TREATED TRANS-3,5-DIHYDROPEROXY-3,5-DIMETHYL-1,2-DIOXOLANE , 2010 .

[3]  L. Ravishankar,et al.  Cerium(III)-Catalyzed Synthesis of Schiff Bases: A Green Approach , 2010 .

[4]  S. Kerwin,et al.  Synthesis and studying the antitumor activity of novel 5-(2-methylbenzimidazol-5-yl)-1,3,4-oxadiazole-2(3H)-thiones , 2010 .

[5]  Babulal Das,et al.  Organocatalyzed One-Pot Synthesis of Substituted 1,5-Benzodiazepine and Benzimidazole Derivatives , 2010 .

[6]  M. Mahmoud,et al.  Heteroannulated Quinazoline and Quinazolinone Derivatives from (Z)-2-[1-Benzamido-2-(3,4,5-trimethoxyphenyl)]vinyl-3,1-benzoxazin-4(3H)-one , 2010 .

[7]  I. A. Hashmi,et al.  Synthesis of Reversed C-Nucleosides , 2010 .

[8]  N. Devanna,et al.  Facile and Simple Synthesis of Novel 1-Methyl-2-(2-substituted-oxazol-4-yl)-1H-benzimidazole Derivatives , 2010 .

[9]  P. M. Reddy,et al.  Synthesis and antimicrobial activities of a new class of 6-arylbenzimidazo[1,2-c]quinazolines , 2010 .

[10]  F. Aldabbagh,et al.  Synthesis of aryl ring-fused benzimidazolequinones using 6-exo-trig radical cyclizations , 2009 .

[11]  Sanjun Zhi,et al.  Microwave-Assisted Catalyst-Free and Solvent-Free Method for the Synthesis of Quinoxalines , 2009 .

[12]  K. Takeda,et al.  One-pot concise syntheses of benzimidazo[2,1-a]isoquinolines by a microwave-accelerated tandem process , 2009 .

[13]  K. Niknam,et al.  Silica Bonded S-Sulfonic Acid: A Recyclable Catalyst for the Synthesis of Quinoxalines at Room Temperature , 2009, Molecules.

[14]  Yueming Sun,et al.  An experimental and computational study of intramolecular charge transfer : Diarylamino derivatives of 7H-benzimidazo(2,1-a)benz(d,e)isoquinolin-7-ones , 2009 .

[15]  D. Konwar,et al.  Practical, Ecofriendly, and Chemoselective Method for the Synthesis of 2-Aryl-1-arylmethyl-1H-benzimidazoles Using Amberlite IR-120 as a Reusable Heterogeneous Catalyst in Aqueous Media , 2009 .

[16]  N. Zhukova,et al.  Fused polycyclic nitrogen-containing heterocycles 21. Condensation of 4-hydroxy-3,5-diphenyl-2-phenyliminothiazolidine with 5-fluoro-4-morpholino- and 4-(4-methylpiperazino)-1,2-phenylenediamines , 2009 .

[17]  Huile Jin,et al.  An efficient catalyst-free protocol for the synthesis of quinoxaline derivatives under ultrasound irradiation , 2009 .

[18]  J. A. Kumar,et al.  Efficient and Inexpensive Synthesis of Benzimidazoles and Quinoxalines , 2008 .

[19]  U. Kazmaier,et al.  Synthesis and reactions of some 5(6)-(1-adamantyl)benzimidazoles , 2008 .

[20]  M. Médebielle,et al.  A CONVENIENT SYNTHESIS OF FLUORINE-CONTAINING DIHYDROBENZO[b][1,4]DIAZEPINOLS AND ITS APPLICATION TO A SYNTHESIS OF NOVEL N-SULFINYLANILINES , 2008 .

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

[22]  Suresh,et al.  RuCl3·xH2O: A Novel and Efficient Catalyst for the Facile Synthesis of 1,5-Benzodiazepines Under Solvent-Free Conditions , 2008 .

[23]  E. De Clercq,et al.  Novel N1-substituted 1,3-dihydro-2H-benzimidazol-2-ones as potent non-nucleoside reverse transcriptase inhibitors. , 2008, Bioorganic & medicinal chemistry.

[24]  A. V. Tsukanov,et al.  Chemosensors based on N-(9-anthrylmethyl)-benzene-1,2-diamine , 2008 .

[25]  M. Doble,et al.  Experimental and QSAR studies on antimicrobial activity of benzimidazole derivatives. , 2008, Chemical & pharmaceutical bulletin.

[26]  H. R. Darabi,et al.  NH 4 Cl-CH 3 OH: an efficient, acid- and metal-free catalyst system for the synthesis of quinoxalines , 2008 .

[27]  A. K. El-ziaty,et al.  Antibacterial Activities of New (E) 2‐Cyano‐3‐(3′,4′‐dimethoxyphenyl)‐2‐propenoylamide Derivatives , 2007 .

[28]  Hui Xu,et al.  A mild and efficient ultrasound-assisted synthesis of diaryl ethers without any catalyst. , 2007, Ultrasonics sonochemistry.

[29]  M. Devereux,et al.  Synthesis, X-ray crystal structures and biomimetic and anticancer activities of novel copper(II)benzoate complexes incorporating 2-(4'-thiazolyl)benzimidazole (thiabendazole), 2-(2-pyridyl)benzimidazole and 1,10-phenanthroline as chelating nitrogen donor ligands. , 2007, Journal of inorganic biochemistry.

[30]  Weisi Li,et al.  Efficient Synthesis of 1,5‐Benzodiazepines Mediated by Sulfamic Acid under Neat Condition or in Solution , 2007 .

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

[32]  H. R. Darabi,et al.  Benign approaches for the microwave-assisted synthesis of quinoxalines , 2007 .

[33]  K. McIntyre,et al.  Synthesis and biological evaluation of 4-amino derivatives of benzimidazoquinoxaline, benzimidazoquinoline, and benzopyrazoloquinazoline as potent IKK inhibitors. , 2007, Bioorganic & medicinal chemistry letters.

[34]  P. Hoffmann,et al.  Versatile Cyclization of Aminoanilino Lactones: Access to Benzotriazoles and Condensed Benzodiazepin‐2‐thiones , 2007 .

[35]  V. Goncharov,et al.  Reaction of 2-(2-oxo-2,3-dihydro-1H-indol-3-ylidene)acetic acid esters with benzene-1,2-diamine and 2-aminobenzenethiol , 2007 .

[36]  M. Preobrazhenskaya,et al.  Heterocyclic analogs of 5,12-naphthacenequinone. 5. Synthesis of 2,3-diamino-1,4-dimethoxyanthraquinone and its heterocyclic derivatives , 2007 .

[37]  A. Lauria,et al.  Isoindolo[2,1-c]benzo[1,2,4]triazines: a new ring system with antiproliferative activity. , 2007, Bioorganic & medicinal chemistry.

[38]  D. Shinde,et al.  Synthesis of antimicrobial 2,9,10-trisubstituted-6-oxo-7,12-dihydro-chromeno[3,4-b]quinoxalines. , 2006, Bioorganic & medicinal chemistry letters.

[39]  V. P. Vaidya,et al.  An Efficient Synthesis of 1,5-Thiadiazepines and 1,5-Benzodiazepines by Microwave-Assisted Heterocyclization , 2006 .

[40]  A. Gubaidullin,et al.  Quinoxaline-benzimidazole rearrangement in the synthesis of benzimidazole-based podands , 2006 .

[41]  H. Fahmy,et al.  Synthesis of novel benzofuran and related benzimidazole derivatives for evaluation ofin vitro anti-HIV-1, anticancer and antimicrobial activities , 2006, Archives of pharmacal research.

[42]  M. Kidwai,et al.  Neat Reaction Technology for the Synthesis of Novel 1,5‐Benzodiazepines , 2006 .

[43]  S. S. Beheshtiha,et al.  Synthesis and Absorption Properties of Some 4-Mercapto-1,8-naphthalimides, 4-Mercapto-7H-benzimidazo[2,1-a]benz[d,e] Isoquinolin-7-one, and 4-Mercapto-7H-benzimidazo [2,1-a]Benz[d, e]isoquinoline-7-one , 2006 .

[44]  R. Mahesh,et al.  Synthesis and biological evaluation of a novel structural type of serotonin 5-HT3 receptor antagonists. , 2006, Bioorganic & medicinal chemistry letters.

[45]  R. Kumar,et al.  Synthesis and anti-bacterial activity of some novel 2-(6-fluorochroman-2-yl)-1-alkyl/acyl/aroyl-1H-benzimidazoles. , 2006, European journal of medicinal chemistry.

[46]  Sherine N. Khattab,et al.  Synthesis of 3-benzyl-2-substituted quinoxalines as novel monoamine oxidase A inhibitors. , 2006, Bioorganic & medicinal chemistry letters.

[47]  Fan Xu,et al.  Efficient Synthesis of 1,5‐Benzodiazepine Derivatives by Ytterbium Trichloride–Catalyzed Condensation of o‐Phenylenediamine and Ketones , 2006 .

[48]  S. Yıldız,et al.  Synthesis and Potent Antimicrobial Activities of Some Novel Retinoidal Monocationic Benzimidazoles , 2006, Archiv der Pharmazie.

[49]  R. Bhosale,et al.  An efficient protocol for the synthesis of quinoxaline derivatives at room temperature using molecular iodine as the catalyst , 2005 .

[50]  A. Mavrova,et al.  Synthesis and antitrichinellosis activity of some 2-substituted-[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-ones. , 2005, Bioorganic & medicinal chemistry.

[51]  V. Saloutin,et al.  3-Methylidene-2,4-dioxo-4-pentafluorophenylbutanoates in the Synthesis of Heterocycles , 2005 .

[52]  B. Rajitha,et al.  Synthesis of Biological Active Chromene Benzothiadiazole Derivatives , 2005 .

[53]  Jun Cheng,et al.  Convenient Method for the Preparation of 2‐Aryl‐1H‐benzimidazole‐4‐carboxylic Acids , 2005 .

[54]  M. Heravi,et al.  Microwave-Assisted Synthesis of Quinoxalines, Benzoxazines, and Benzothiazines Under Solvent-Free Conditions , 2005 .

[55]  A. Monge,et al.  Synthesis of new quinoxaline-2-carboxylate 1,4-dioxide derivatives as anti-Mycobacterium tuberculosis agents. , 2005, Journal of medicinal chemistry.

[56]  R. Taylor,et al.  Quinoxaline synthesis from α-hydroxy ketones via a tandem oxidation process using catalysed aerobic oxidation , 2005 .

[57]  A. Gomtsyan,et al.  Novel transient receptor potential vanilloid 1 receptor antagonists for the treatment of pain: structure-activity relationships for ureas with quinoline, isoquinoline, quinazoline, phthalazine, quinoxaline, and cinnoline moieties. , 2005, Journal of medicinal chemistry.

[58]  S. Goldstein,et al.  Cytotoxic and antitumoral properties in a series of new, ring D modified, olivacine analogues. , 2005, Bioorganic & medicinal chemistry.

[59]  M. Kodess,et al.  Reactions of alkyl 2-benzylidene-2-polyfluoroacylacetates with N,N-dinucleophiles , 2004 .

[60]  Yun-Bong Kim,et al.  Synthesis and biological activity of new quinoxaline antibiotics of echinomycin analogues. , 2004, Bioorganic & medicinal chemistry letters.

[61]  Yu. E. Sapozhnikov,et al.  Acyl Derivatives of 2-Aminobenzimidazole and Their Fungicide Activity , 2004 .

[62]  C. Suresh Reddy,et al.  Synthesis and antimicrobial activity of novel phosphorus heterocycles with exocyclic p-C link. , 2004, Chemical & pharmaceutical bulletin.

[63]  S. N. Reddy,et al.  Studies on the reaction of unsymmetrical trifluoromethyl 1,2-phenylenediamine with various ketones leading to novel fluorinated heterocycles , 2003 .

[64]  N. Curtin,et al.  Tricyclic benzimidazoles as potent poly(ADP-ribose) polymerase-1 inhibitors. , 2003, Journal of medicinal chemistry.

[65]  V. Orlov,et al.  Reaction of 3-Benzoyl-2,3-dibromopropionic Acid with Substituted ortho-Phenylenediamines , 2002 .

[66]  R. Reynolds,et al.  Synthesis and antimycobacterial activity of pyrazine and quinoxaline derivatives. , 2002, Journal of medicinal chemistry.

[67]  Manish P. Patel,et al.  Monoazo disperse dyes derived from 11H-7-amino-2-chloro-isoindolo[2,1-a] benzimidazole-11-one , 2002 .

[68]  E. De Clercq,et al.  Synthesis and anti-hIV activity of 1-(2,6-difluorophenyl)-1H,3H-thiazolo[3,4-a]benzimidazole structurally-related 1,2-substituted benzimidazoles. , 2002, Farmaco.

[69]  S. Hazeldine,et al.  II. Synthesis and biological evaluation of some bioisosteres and congeners of the antitumor agent, 2-(4-[(7-chloro-2-quinoxalinyl)oxy]phenoxy)propionic acid (XK469). , 2002, Journal of medicinal chemistry.

[70]  N. Sonawane,et al.  Synthesis and application of 2‐styryl‐6,7‐dichlorothiazolo[4,5‐b]‐quinoxaline based fluorescent dyes: Part 3 , 2002 .

[71]  S. S. Ibrahim,et al.  Synthesis and Reactions of Some 2-Methyl-4-oxo-4 H -1-benzopyrans and 2-Methyl-4-oxo-4 H -1-benzo[ b ]-thiopheno[3,2- b ]pyrans , 2002 .

[72]  M. Marongiu,et al.  1,5-Benzodiazepines. Part XII. Synthesis and biological evaluation of tricyclic and tetracyclic 1,5-benzodiazepine derivatives as nevirapine analogues. , 2001, European journal of medicinal chemistry.

[73]  F. Foti,et al.  Reactions of 3-substituted chromones with ortho-phenylenediamine , 2001 .

[74]  A. Da Settimo,et al.  Synthesis, in vitro antiproliferative activity and DNA-interaction of benzimidazoquinazoline derivatives as potential anti-tumor agents. , 2001, Farmaco.

[75]  D. Lawrence,et al.  Structure-activity studies of substituted quinoxalinones as multiple-drug-resistance antagonists. , 2001, Journal of medicinal chemistry.

[76]  Y. Tabuchi,et al.  Characterization of the mouse TFF1 (pS2) gene promoter region. , 2001, Biological & pharmaceutical bulletin.

[77]  C. Kumar,et al.  CONDENSATION OF O-PHENYLENEDIAMINE WITH CINNAMIC ACIDS , 2001 .

[78]  M. C. Rezende,et al.  AN ALTERNATIVE PREPARATION OF BISBENZIMIDAZOLES , 2001 .

[79]  A. Babu,et al.  ONE-POT SYNTHESIS OF 1,3,5-BENZOTRIAZEPINES , 2001 .

[80]  I. Sage,et al.  Synthesis and device characterisation of side-chain polymer electron transport materials for organic semiconductor applications , 2001 .

[81]  I. Kawasaki,et al.  Synthesis of a regio-isomer of kealiiquinone, a marine benzimidazole alkaloid , 2001 .

[82]  F. Latif.  An improved synthesis of pyrazolo[3,4‐b][1,5]benzoxazepine, ‐benzothiazepine and ‐benzodiazepine derivatives via a convenient one‐pot synthesis , 2000 .

[83]  A. Guirado,et al.  A new synthetic route to 1-chlorophenazines. The electrochemical monodechlorination of 3,3,6,6-tetrachloro-1,2-cyclohexanedione as a key step , 2000 .

[84]  H. Abdel-ghany,et al.  SYNTHESIS OF POLYFUSED THIENO(2,3-b)THIOPHENES PART 1: SYNTHESIS OF THIENOPYRIMIDINE DERIVATIVES , 2000 .

[85]  M. Ismail,et al.  Synthesis and Antimicrobial Activities of Some Novel Quinoxalinone Derivatives , 2000 .

[86]  I. M. El‐Deen,et al.  Synthesis and Chemical Behavior of 2-Chloro -3-(2″-Thienoylmethyl) Quinoxaline Towards Some Nucleophilic Reagents , 2000 .

[87]  P. Koutentis,et al.  Cyclisation chemistry of 4H-1,2,6-thiadiazines , 2000 .

[88]  V. Kanetkar,et al.  SYNTHESIS AND APPLICATION OF ETHYL 3-(4-DIALKYLAMINOPHENYL)-2-(QUINOXALIN-3(4H)-ON-2-YL)PROPENOATES AND RELATED PRODUCTS , 1999 .

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

[90]  G. Tóth,et al.  Regioselectivity in preparation of unsymmetrically substituted 3-aminoquinoxalin-2(1H)-ones , 1999 .

[91]  B. Nordén,et al.  Interactions of the antiviral quinoxaline derivative 9-OH-B220 [2, 3-dimethyl-6-(dimethylaminoethyl)- 9-hydroxy-6H-indolo-[2, 3-b]quinoxaline] with duplex and triplex forms of synthetic DNA and RNA. , 1998, Journal of molecular biology.

[92]  J. Girardet,et al.  Design, synthesis, and antiviral activity of alpha-nucleosides: D- and L-isomers of lyxofuranosyl- and (5-deoxylyxofuranosyl)benzimidazoles. , 1998, Journal of medicinal chemistry.

[93]  H. Fun,et al.  Syntheses and electronic structures of benzannelated isoquinolinones and their photoinduced cycloaddition reactions with electron deficient alkenes , 1998 .

[94]  Liu Yang,et al.  THE SYNTHESIS OF QUINOXALINES BY CONDENSATION REACTION OF ACYLEINS WITH O-PHENYLENEDIAMINE WITHOUT SOLVENT UNDER MICROWAVE IRRADIATION , 1998 .

[95]  C. Avendaño,et al.  Applications of Ethyl Carboethoxyformimidate to Heterocyclic Synthesis: Preparation of Condensed Pyrazinones and 1,4-Oxazinones , 1997 .

[96]  A. M. El-sayed,et al.  A Novel Synthesis of Heterocyclic Compounds Derived from α-Ketoketene S,S-Acetal , 1996 .

[97]  Donal D. C. Bradley,et al.  Use of poly(phenyl quinoxaline) as an electron transport material in polymer light‐emitting diodes , 1996 .

[98]  G. Mcmahon,et al.  Tyrphostins. 5. Potent inhibitors of platelet-derived growth factor receptor tyrosine kinase: structure-activity relationships in quinoxalines, quinolines, and indole tyrphostins. , 1996, Journal of medicinal chemistry.

[99]  M. Cava,et al.  Synthesis of Thieno[3,4-b]quinoxaline and Derivatives , 1995 .

[100]  M. Nassiri,et al.  Design, synthesis, and antiviral activity of certain 2,5,6-trihalo-1-(beta-D-ribofuranosyl)benzimidazoles. , 1995, Journal of medicinal chemistry.

[101]  H. Suschitzky,et al.  2H-benzimidazoles (isobenzimidazoles). Part 10. Synthesis of polysubstituted o-phenylenediamines and their conversion into heterocycles, particularly 2-substituted benzimidazoles with known or potential anthelminthic activity , 1995 .

[102]  M. Cherkaoui,et al.  Synthesis of New Adamantylated Heterocycles , 1994 .

[103]  C. Yu,et al.  Antineoplastic activity of benzimidazo[1,2-b]-isoquinolines, indolo[2,3-b]quinolines, and pyridocarbazoles. , 1994, Bioorganic & medicinal chemistry.

[104]  G. Bernáth,et al.  Preparation and steric structure of tricyclic and tetracyclic saturated or partially saturated 1,3-heterocycles containing a saturated isoindolone moiety , 1994 .

[105]  R. Perry,et al.  A novel palladium-catalyzed synthesis of 2-arylbenzimidazoles , 1993 .

[106]  K. Ando,et al.  Alkylation of 4H,6H-thieno[3,4-c]furan 5,5-dioxide and its use as a 3,4-dimethylenefuran synthon in intramolecular Diels–Alder reaction , 1993 .

[107]  E. Luk'yanets,et al.  Some new reactions of coumarins , 1992 .

[108]  T. Chou,et al.  Preparation and Reactions of Thiazole-Fused 3-Sulfolenes. Useful Precursors to o-Dimethylene Thiazoles. , 1992 .

[109]  Takashi Hayashi,et al.  Synthesis and Some Reactions of 2-(2-Aminoanilino)cyclohepta[b]pyrroles: Leading to 5H-Cyclohepta[1′,2′: 4,5]pyrrolo[2,3-b][1,5]benzodiazepine, a Novel 20π Antiaromatic System, and Cydohepta[1′,2′: 4,5] pyrrolo[1,2-a]benzimidazoles , 1990 .

[110]  T. Nishio.  Photochemical reactions of quinoxalin-2-ones and related compounds , 1990 .

[111]  A. Bhaduri,et al.  Syntheses and bioevaluation of substituted dihydropyridines for pregnancy-interceptive activity in hamsters. , 1989, Journal of Medicinal Chemistry.

[112]  H. Zimmer,et al.  Dibromotriphenylphosphorane promoted synthesis of condensed heterocyclic systems from aromatic diamines , 1988 .

[113]  K. Makino,et al.  Regent progress in the quinoxaline chemistry. Synthesis and biological activity , 1988 .

[114]  A. F. Temple,et al.  Some novel heterocyclic systems derived from 7-amino-2,3-dihydro-8-nitro-1H-pyrrolo[1,2-α]benzimidazole and the corresponding diamine , 1987 .

[115]  T. Aminabhavi,et al.  New routes to poly(benzylenebenzimidazoles) , 1986 .

[116]  R. K. Robins,et al.  Synthesis and biological activity of 6-azacadeguomycin and certain 3,4,6-trisubstituted pyrazolo[3,4-d]pyrimidine ribonucleosides. , 1985, Journal of Medicinal Chemistry.

[117]  K. C. Eapen,et al.  Reactions of 1,2-bis(trifluoroacetyl)benzene with nucleophiles leading to heterocyclic compounds , 1985 .

[118]  R. Kellogg,et al.  Synthesis and chemistry of 2,2,5,5-tetramethylthiolane-3,4-dione. A route to bicyclo[2.1.0]pentyl-1-sulfonium intermediates , 1982 .

[119]  W. Pfleiderer,et al.  Nucleoside, XXXVIII. Synthese und Eigenschaften von 1‐(β‐D‐Ribofuranosyl)‐2‐chinoxalinonen und ‐2,3‐chinoxalindionen , 1982 .

[120]  C. Avendaño,et al.  Heterocyclic synthesis using ethyl carboethoxyformimidate , 1982 .

[121]  D. Williams,et al.  Structure revision of the antibiotic echinomycin. , 1975, Journal of the American Chemical Society.

[122]  E. Moriconi,et al.  Sulfur dioxide extrusion from 1,3-diphenyl-1,3-dihydrothieno[3,4-b]quinoxaline 2,2-dioxides. A new synthesis of 6-phenylbenzo[b]phenazines , 1969 .

[123]  E. Moriconi,et al.  The Dimethyl Sulfoxide Oxidation of 2,3-Bis(bromomethyl)quinoxaline1,2 , 1965 .

[124]  M. Joullié,et al.  The Ionization Constants, Ultraviolet and Infrared Spectra of Some Substituted Benzimidazoles , 1964 .

[125]  J. Michalský.  Über die roten Anile. Darstellung von α‐(p‐Dialkylaminophenylimino)‐β‐keto‐phthalimido‐alkancarbonsäurenitrilen , 1959 .

[126]  D. W. Hein,et al.  The Use of Polyphosphoric Acid in the Synthesis of 2-Aryl- and 2-Alkyl-substituted Benzimidazoles, Benzoxazoles and Benzothiazoles1 , 1957 .

[127]  K. Trueblood,et al.  Structure of Vitamin B12 : The Crystal Structure of the Hexacarboxylic Acid derived from B12 and the Molecular Structure of the Vitamin , 1955, Nature.

[128]  H. Rydon,et al.  Polyazanaphthalenes. Part I. Some derivatives of 1:4:5-triazanaphthalene and quinoxaline , 1955 .

[129]  J. P. Lambooy,et al.  Synthesis of D-Riboflavin-2-C14 and its Metabolism by Lactobacillus casei1 , 1954 .

[130]  J. H. Boyer,et al.  Azidocarbonyl Compounds. II. The Pyrolysis of α-Azidocarbonyl Compounds1a , 1953 .

[131]  J. K. Landquist.  567. Quinoxaline N-oxides. Part I. The oxidation of quinoxaline and its Bz-substituted derivatives , 1953 .

[132]  C. K. Banks,et al.  2-Hydroxy-3-alkylquinoxalines , 1951 .

[133]  R. Kuhn,et al.  Ringschlüsse mit α,α′‐Dioxymuconsäure‐estern , 1951 .

[134]  J. Clark‐Lewis,et al.  744. The constitution of products formed from o-phenylenediamines and alloxan in neutral solution , 1951 .

[135]  G. Newbold,et al.  543. Quinoxaline oxides. Part II. The action of hydrochloric acid on 3-ethoxy-2-methylquinoxaline 1-oxide , 1949 .

[136]  M. Tishler,et al.  3,4-Dihydro-3-keto-4,6,7-trimethyl-2-quinoxalinecarboxylic acid. , 1947, Journal of the American Chemical Society.

[137]  M. A. Phillips.  CCCXVII.—The formation of 2-substituted benziminazoles , 1928 .

[138]  G. A. R. Kon,et al.  LXXV.—Ring-chain tautomerism. Part I. The occurrence and effect of keto-enol tautomerism between a ring compound and its open-chain isomeride , 2022 .

[139]  O. Hinsberg.  Ueber einige Chinoxalinabkömmlinge , 2022 .