Isocyanide‐Based Three‐Component Synthesis of Pyrano‐pyrido‐quinoxalines

by Roya Akbarzadeh, Tayebeh Amanpour, Peiman Mirzaei, and Ayoob Bazgir*Department of Chemistry, Shahid Beheshti University, G. C. Tehran, 1983963113, Iran(e-mail: a_bazgir@sbu.ac.ir)Pyrano-pyrido-quinoxaline derivatives were synthesized in good yields by a three-componentreaction of isocyanides, dialkyl acetylenedicarboxylates, and pyrido[1,2-a]quinoxaline-triones in DMFat1008.

[1]  M. Adib,et al.  Synthesis of 2-(alkylamino)-5-{alkyl[(2-oxo-2H-chromen-3-yl)carbonyl]amino}-3,4-furandicarboxylates using a multi-component reaction in water , 2010 .

[2]  P. Mirzaei,et al.  A simple synthesis of ferrocenyl bis-amides by a Ugi four-component reaction , 2010 .

[3]  A. Bazgir,et al.  An efficient synthesis of ferrocenyl imidazo[1,2-a]pyridines , 2010 .

[4]  M. Adib,et al.  A multi-component synthesis of 3-aryl-1-(arylmethylideneamino)pyrrolidine-2,5-diones , 2010 .

[5]  A. Bazgir,et al.  Grindstone chemistry: one-pot synthesis of spiro(diindenopyridine-indoline) triones and spiro(acenaphthylene-diindenopyridine)triones , 2010 .

[6]  A. Bazgir,et al.  One-pot, pseudo four-component synthesis of a spiro[diindeno[1,2-b:2',1'-e]pyridine-11,3'-indoline]-trione library. , 2010, Journal of combinatorial chemistry.

[7]  Chunju Li,et al.  CAN-catalyzed syntheses of 3,4-dihydroquinoxalin-2-amine derivatives based on isocyanides , 2009 .

[8]  P. Mirzaei,et al.  Synthesis of spiro[benzopyrazolonaphthyridine-indoline]-diones and spiro[chromenopyrazolopyridine-indoline]-diones by one-pot, three-component methods in water , 2009 .

[9]  M. Bayat,et al.  An Efficient Synthesis of Functionalized6,10-Dioxo-6,10-dihydro-5H-pyrido[1,2-a]quinoxalines and 6,10-Dioxo-6,10-dihydropyrido[2,1-c][1,4]benz­oxazines , 2009 .

[10]  A. Shaabani,et al.  Synthesis of fully substituted pyrano[2,3-c]pyrazole derivatives via a multicomponent reaction of isocyanides , 2009 .

[11]  A. Bazgir,et al.  Novel one-pot, three-component synthesis of spiro[indoline-pyrazolo[4',3':5,6]pyrido[2,3-d]pyrimidine]trione library. , 2009, Journal of combinatorial chemistry.

[12]  A. Bazgir,et al.  Efficient synthesis of spiro[chromeno[2,3-d]pyrimidine-5,3'-indoline]-tetraones by a one-pot and three-component reaction. , 2009, Journal of combinatorial chemistry.

[13]  M. Heravi,et al.  A novel three-component reaction for the synthesis of N-cyclohexyl-3-aryl-quinoxaline-2-amines , 2009 .

[14]  A. Shaabani,et al.  A simple and efficient approach to the synthesis of 4H-furo[3,4-b]pyrans via a three-component reaction of isocyanides. , 2008, Bioorganic & medicinal chemistry letters.

[15]  M. Teimouri,et al.  Simple synthesis of 7H-phenaleno[1,2-b]furan-7-one derivatives by one-pot, three-component reactions. , 2008, Journal of combinatorial chemistry.

[16]  G. Basso,et al.  Isoindolo[2,1-a]quinoxaline derivatives, novel potent antitumor agents with dual inhibition of tubulin polymerization and topoisomerase I. , 2008, Journal of medicinal chemistry.

[17]  A. Maleki,et al.  Novel isocyanide-based three-component synthesis of 3,4-dihydroquinoxalin-2-amine derivatives. , 2008, Journal of combinatorial chemistry.

[18]  H. Khavasi,et al.  One-pot three-component regioselective synthesis of linear naphtho[2,3-b]-furan-4,9-diones , 2007 .

[19]  S. Fujiwara,et al.  Copper(I)-catalyzed highly efficient synthesis of benzoselenazoles and benzotellurazoles. , 2007, The Journal of organic chemistry.

[20]  I. Yavari,et al.  One-Pot Synthesis of Pentaalkyl 7-[(Alkylamino)carbonyl]-2-oxa-1-azabicyclo[3.2.0]hept-3-ene-3,4,5,6,7-pentacarboxylate , 2006 .

[21]  H. Khavasi,et al.  An isocyanide-based three-component reaction: synthesis of fully substituted N-alkyl-2-triphenylphosphoranylidene glutarimides , 2006 .

[22]  Leila Mohammadi,et al.  Reaction of tert-butyl isocyanide and dialkyl acetylenedicarboxylates in the presence of 2-acetylbutyrolactone. Synthesis of functionalized α-methylene-γ-butyrolactones , 2006 .

[23]  A. Maleki,et al.  Ionic liquid promoted one-pot synthesis of 3-aminoimidazo[1,2-a]pyridines , 2006 .

[24]  M. Teimouri,et al.  Reaction between isocyanides and dialkyl acetylenedicarboxylates in the presence of strong CH-acids: one-pot synthesis of highly functionalized annulated 4H-pyrans , 2006 .

[25]  Alexander Dömling,et al.  Recent developments in isocyanide based multicomponent reactions in applied chemistry. , 2006, Chemical reviews.

[26]  M. Esnaashari,et al.  Three-Component One-Pot Synthesis of Functionalized 1,2,3,6-Tetrahydropyrano[4,3-b]pyrroles , 2005 .

[27]  N. Ghosh,et al.  Synthesis and pharmacological evaluation of substituted 5-[4-[2-(6,7-dimethyl-1,2,3,4-tetrahydro-2-oxo-4-quinoxalinyl)ethoxy]phenyl]methylene]thiazolidine-2,4-dione derivatives as potent euglycemic and hypolipidemic agents. , 2005, Bioorganic & medicinal chemistry letters.

[28]  A. Shaabani,et al.  Introducing a novel class of four-component reactions , 2004, Molecular Diversity.

[29]  C. D. Wilfred,et al.  Preparation of quinoxalines, dihydropyrazines, pyrazines and piperazines using tandem oxidation processes. , 2003, Chemical communications.

[30]  Jieping Zhu.  Recent Developments in the Isonitrile‐Based Multicomponent Synthesis of Heterocycles , 2003 .

[31]  James R. Burke,et al.  BMS-345541 Is a Highly Selective Inhibitor of IκB Kinase That Binds at an Allosteric Site of the Enzyme and Blocks NF-κB-dependent Transcription in Mice* , 2003, The Journal of Biological Chemistry.

[32]  I. Ugi,et al.  The Chemistry of Isocyanides, their MultiComponent Reactions and their Libraries† , 2003, Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry.

[33]  C. Hulme,et al.  "Multi-component reactions : emerging chemistry in drug discovery" 'from xylocain to crixivan'. , 2003, Current medicinal chemistry.

[34]  R. Menon,et al.  An efficient multicomponent reaction involving the interception of the zwitterionic intermediate between DMAD and isocyanides with some active methylene compounds , 2002 .

[35]  M. Adib,et al.  Reaction between isocyanides and dialkyl acetylenedicarboxylates in the presence of 3-methylcyclopentane-1,2,4-trione. One-pot diastereoselective synthesis of tetrahydrocyclopenta[b]pyran derivatives , 2002 .

[36]  I. Ugi,et al.  Multicomponent Reactions with Isocyanides. , 2000, Angewandte Chemie.

[37]  L. Tietze,et al.  Multicomponent domino reactions for the synthesis of biologically active natural products and drugs , 2000, Medicinal research reviews.

[38]  J. Li.  Synthesis of Novel 3-Substituted Pyrrolo[2,3-b]quinoxalines via an Intramolecular Heck Reaction on an Aminoquinoxaline Scaffold. , 1999, The Journal of organic chemistry.

[39]  Alan R. Katritzky,et al.  Comprehensive Heterocyclic Chemistry IV , 1996 .

[40]  P. Ornstein,et al.  Synthesis and excitatory amino acid pharmacology of a series of heterocyclic-fused quinoxalinones and quinazolinones. , 1992, Journal of medicinal chemistry.

[41]  B. K. Trivedi,et al.  [1,2,4]Triazolo[4,3-a]quinoxalin-4-amines: a new class of A1 receptor selective adenosine antagonists. , 1988, Journal of medicinal chemistry.

[42]  G. M. Badger,et al.  The chemistry of heterocyclic compounds , 1961 .