Microwave-Assisted Synthesis of Quinoxalines, Benzoxazines, and Benzothiazines Under Solvent-Free Conditions

The addition of dialkyl acetylenedicarboxylate to o-phenylenediamine, o-aminophenol, and o-aminothiophenol under microwave irradiation in solventless system rapidly afforded quinoxaline, benzoxazine, and benzothiazine derivatives, respectively.

[1]  M. Rahimizadeh,et al.  Pd–Cu catalyzed heterocyclization during Sonogashira coupling: synthesis of 3-benzylthiazolo[3,2-a]benzimidazole , 2004 .

[2]  M. Heravi,et al.  Regeneration of Carbonyl Compounds from Phenylhydrazones Under Microwave Irradiation , 2002 .

[3]  M. Rahimizadeh,et al.  Sulfuric Acid: A Mild Catalyst for the Regioselective Synthesis of 2-Substituted [1,2,4]Triazolo[5,1-b][1,3]thiazin-7-ones , 2001 .

[4]  G. Rajabzadeh,et al.  A CONVENIENT AND GENERAL SYNTHESIS OF A NOVEL HETEROCYCLIC SYSTEM; 5H-[1,3,4]THIADIAZOLO[2,3-d] [1,2,4]TRIAZIN-5-ONES , 2001 .

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

[6]  M. M. Heravi,et al.  Reaction of Dimethyl Acetylene-Dicarobxylate With Triazinone , 2000 .

[7]  M. Ghassemzadeh,et al.  Zeolite-induced Heterocyclization: A Superior Method of Synthesis of Condensed Imidazoles† , 2000 .

[8]  M. Heravi,et al.  A convenient oxidative deprotection of tetrahydropyranyl ethers with iron(III) nitrate and clay under microwave irradiation in solvent free conditions , 1999 .

[9]  M. Heravi,et al.  ‘Zeofen’, a user-friendly oxidizing reagent , 1999 .

[10]  A. Monteil,et al.  New substituted 1,4-benzoxazine derivatives with potential intracellular calcium activity. , 1998, Journal of medicinal chemistry.

[11]  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.

[12]  M. Mafi,et al.  Regioselective N-Methylation of Methylthio-Substituted Pyrimidinones and 1,2,4-Triazinone with Methanol over H-Y Zeolite. , 1997 .

[13]  M. Maghsoodlou,et al.  REACTION BETWEEN 1,10-PHENANTHROLINE AND DIALKYL ACETYLENEDICARBOXYLATES. A FACILE SYNTHETIC ROUTE TO HELICAL DIPYRROLOPHENANTHROLINES , 1997 .

[14]  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.

[15]  Y. Okamoto,et al.  1H-NMR study on the tautomer ratios between the hydrazone imine and diazenylenamine forms in 3-(arylhydrazono)-methyl-2-oxo-1,2-dihydroquinoxalines , 1996 .

[16]  Mark E. Davis,et al.  Studies on the Catalytic-Oxidation of Alkanes and Alkenes by Titanium Silicates , 1994 .

[17]  M. Kajino,et al.  Synthesis and biological activities of new 2-substituted 1,4-benzoxazine derivatives. , 1991, Chemical & pharmaceutical bulletin.

[18]  J. Stowell,et al.  Concurrent strong acid and base catalysis. Synthesis of cyclopentenones , 1981 .

[19]  J. Wallis,et al.  Addition reactions of heterocyclic compounds. Part 74. Products from dimethyl acetylenedicarboxylate with thiourea, thioamide, and guanidine derivatives , 1981 .

[20]  R. Acheson,et al.  Reactions of Acetylenecarboxylic Esters with Nitrogen-Containing Heterocycles , 1979 .

[21]  I. Weinryb,et al.  Synthesis and central nervous system activity of 2-arylidene-4-aminoalkyl-2H-1,4-benzoxazin-3(4H)-ones and related compounds. , 1977, Journal of medicinal chemistry.

[22]  H. Suschitzky,et al.  Synthesis of quinoxalinones by the reaction of o-phenylenediamines with dimethyl acetylenedicarboxylate , 1975 .

[23]  Y. Iwanami The Reaction of Acetylenecarboxylic Acid with Amines. XV. Reaffirmation of the Enamine Structure Facilitated by Intramolecular Hydrogen Bonding Common to the Reaction Products , 1971 .

[24]  S. Kalbag,et al.  On the structure of the product of the reaction of 2-aminothiophenol with diethyl acetylene dicarboxylate , 1967 .

[25]  Y. Iwanami The Reaction of Diethyl Acetylenedicarboxylate with o-Aminothiophenol , 1962 .

[26]  泰夫 岩波 アセチレンカルボン酸とアミンとの反応(第3~4報) (第3報)アセチレンジカルボン酸とο-フェニレンジアミンとの反応 , 1961 .