Ecofriendly and Efficient One-Pot Procedure for the Synthesis of Quinazoline Derivatives Catalyzed by an Acidic Ionic Liquid Under Aerobic Oxidation Conditions

REFERENCES

• (a) Zhu , J. ; Bienaymé , H. (Eds.) . Multicomponent Reactions ; Wiley-VCH : Weinheim , Germany , 2005 ; (b) Ramon , D. J. ; Yus , M. Asymmetric multicomponent reactions (AMCRs): The new frontier. Angew. Chem., Int. Ed. 2005, 44, 1602 ; (c) Nair , V. ; Rajesh , C. ; Vinod , A. U. ; Bindu , S. ; Sreekenth , A. R. ; Balagopal , L. Strategies for heterocyclic construction via novel multicomponent reactions based on isocyanides and nucleophilic Carbenes. Acc. Chem. Res. 2003, 36, 899 ; (d) Orru , R. V. A. ; De Greef , M. Recent advances in solution-phase multicomponent methodology for the synthesis of heterocyclic compounds. Synthesis 2003, 1471 ; (e) Balme , G. ; Bossharth , E. ; Monteiro , N. Pd-assisted multicomponent synthesis of heterocycles. Eur. J. Org. Chem. 2003, 4101 ; (f) Dömling , A. ; Ugi , I. Multicomponent reactions with isocyanides. Angew. Chem., Int. Ed. 2000, 39, 3169 ; (g) Bienaymé , H. ; Hulme , C. ; Oddon , G. ; Schmitt , P. Maximizing synthetic efficiency: Multicomponent transformations lead the way. Chem. Eur. J. 2000, 3321 ; (h) Weber , L. ; Illgen , K. ; Almstetter , M. Discovery of new multicomponent reactions with combinatorial methods. Synlett 1999, 366 .
   Google Scholar
• (a) Nicolaou , K. C. ; Vourloinis , D. ; Winssinger , N. ; Baran , P. S. The art and science of total synthesis at the dawn of the twenty-first century . Angew. Chem., Int. Ed. 2000 , 39 , 45 ; (b) Arya , P. ; Chou , D. T. H. ; Back , M. G. Diversity-based organic synthesis in the era of genomics and proteomics . Angew. Chem., Int. Ed. 2001 , 40 , 339 .
   Web of Science ®Google Scholar
• (a) Johne , S. The Alkaloids, Chemistry and Pharmacology ; A. Brossi (Ed.); Academic Press , New York , 1986 ; vol. 29 , chap. 2; (b) Henderson , E. A. ; Bavetsias , V. ; Theti , D. S. ; Wilson , S. C. ; Clauss , R. ; Jackman , A. L. Targeting the α-folate receptor with cyclopenta[g]quinazoline-based inhibitors of thymidylate synthase. Bioorg. Med. Chem. 2006, 14, 5020 ; (c) Herget , T. ; Freitag , M. ; Morbitzer , M. ; Kupfer , R. ; Stamminger , T. ; Marschall , M. Novel chemical class of pUL97 protein kinase-specific inhibitors with strong anticytomegaloviral activity. Antimicrob. Agents Chemother. 2004, 48, 4154 .
   Google Scholar
• (a) Bridges , A. J. Chemical inhibitors of protein kinases . Chem. Rev. 2001 , 101 , 2541 ; (b) Tsou , H. R. ; Mamuya , N. ; Johnson , B. D. ; Reich , M. F. ; Gruber , B. C. ; Ye , F. ; Nilakantan , R. ; Shen , R. ; Discafani , C. ; DeBlanc , R. ; Davis , R. ; Koehn , R. E. ; Greenberger , L. M. ; Wang , Y. F. ; Wissner , A. 6-Substituted-4-(3-bromophenylamino)quinazolines as putative irreversible inhibitors of the epidermal growth factor receptor (EGFR) and human epidermal growth factor receptor (HER-2) tyrosine kinases with enhanced antitumor activity . J. Med. Chem. 2001 , 44 , 2719 ; (c) Berger , M. ; Albrecht , B. ; Berces , A. , Ettmayer , P. ; Neruda , W. ; Woisetschlager , M. S(+)-4-(1-Phenylethylamino)quinazolines as inhibitors of human immunoglobulin E synthesis: Potency is dictated by stereochemistry and atomic point charges at N-1 . J. Med. Chem. 2001 , 44 , 3031 .
   PubMed Web of Science ®Google Scholar
• (a) Yokoyama , K. ; Ishikawa , N. ; Igarashi , S. ; Kawano , N. ; Hattori , K. ; Miyazaki , T. ; Ogino , S. I. ; Matsumoto , Y. ; Takeuchi , M. ; Ohta , M. Discovery of potent CCR4 antagonists: Synthesis and structure–activity relationship study of 2,4-diaminoquinazolines . Bioorg. Med. Chem. 2008 , 16 , 7021 ; (b) Yokoyama , K. ; Ishikawa , N. ; Igarashi , S. ; Kawano , N. ; Masuda , N. ; Hattori , K. ; Miyazaki , T. ; Ogino , S. I. ; Orita , M. ; Matsumoto , Y. ; Takeuchi , M. ; Ohta , M. Potent CCR4 antagonists: Synthesis, evaluation, and docking study of 2,4-diaminoquinazolines . Bioorg. Med. Chem. 2008 , 16 , 7968 .
   PubMed Web of Science ®Google Scholar
• Alexandre , F.-R. ; Berecibar , A. ; Wrigglesworth , R. ; Besson , T. Novel series of 8H-quinazolino[4,3-b]quinazolin-8-ones via two Niementowski condensations. Tetrahedron 2003, 59, 1413.
   Web of Science ®Google Scholar
• Tobe , M. ; Isobe , Y. ; Tomizawa , H. ; Nagasaki , T. ; Takahashi , H. ; Fukazawa , T. ; Hayashi , H. Discovery of quinazolines as a novel structural class of potent inhibitors of NF-κB activation . Bioorg. Med. Chem. 2003 , 11 , 383 .
   PubMed Web of Science ®Google Scholar
• Akazome , M. ; Yamamoto , J. ; Kondo , T. ; Watanabe , Y. Palladium complex–catalyzed intermolecular reductive N-heterocyclization: Novel synthesis of quinazoline derivatives from 2-nitrobenzaldehyde or 2-nitrophenyl ketones with formamide . J. Organomet. Chem. 1995 , 494 , 229 .
   Web of Science ®Google Scholar
• (a) Hill , M. D. ; Movassaghi , M. Direct synthesis of substituted pyrimidines and quinazolines . Synthesis 2008 , 823 ; (b) Sakai , N. ; Youichi , A. ; Sasada , T. ; Konakahara , T. New approach to the practical synthesis of tri- or tetrasubstituted pyrimidine derivatives: A four-component coupling reaction from a functionalized silane, two types of aromatic nitriles, and acetals . Org. Lett. 2005 , 7 , 4705 ; (c) Yoon , D. S. ; Han , Y. ; Stark , T. M. ; Haber , J. C. ; Gregg , B. T. ; Stankovich , S. B. Efficient synthesis of 4-aminoquinazoline and thieno[3,2-d]pyrimidin-4-ylamine derivatives by microwave irradiation . Org. Lett. 2004 , 6 , 4775 ; (d) Kakiya , H. ; Yagi , K. ; Shinokubo , H. ; Oshima , K. Reaction of α,α-dibromo oxime ethers with Grignard reagents: Alkylative annulation providing a pyrimidine core . J. Am. Chem. Soc. 2002 , 124 , 9032 .
   Google Scholar
• (a) Chinchilla , R. ; Nájera , C. ; Yus , M. Metalated heterocycles and their applications in synthetic organic chemistry . Chem. Rev. 2004 , 104 , 2667 ; (b) Turck , A. ; Plé , N. ; Mongin , F. ; Quéguiner , G. Advances in the directed metallation of azines and diazines (pyridines, pyrimidines, pyrazines, pyridazines, quinolines, benzodiazines, and carbolines), part 2: Metallation of pyrimidines, pyrazines, pyridazines, and benzodiazines . Tetrahedron 2001 , 57 , 4489 .
   PubMed Web of Science ®Google Scholar
• (a) Marzaro , G. ; Chilin , A. ; Pastorini , G. ; Guiotto , A. A novel convenient synthesis of benzoquinazolines . Org. Lett. 2006 , 8 , 255 ; (b) Chilin , A. ; Marzaro , G. ; Zanatta , S. ; Barbieri , V. ; Pastorini , G. ; Manzini , P. ; Guiotto , A. A new access to quinazolines from simple anilines . Tetrahedron 2006 , 62 , 12351 .
   PubMed Web of Science ®Google Scholar
• Ferrini , S. ; Ponticelli , F. ; Taddei , M. Convenient synthetic approach to 2,4-disubstituted quinazolines . Org. Lett. 2007 , 9 , 69 .
   PubMed Web of Science ®Google Scholar
• Shi , D. ; Rong , L. ; Wang , J. ; Zhuang , Q. ; Wang , X. ; Hu , H. Synthesis of quinazolin-4(3H)-ones and 1,2-dihydroquinazolin-4(3H)-ones with the aid of a low-valent titanium reagent . Tetrahedron Lett. 2003 , 44 , 3199 .
   Web of Science ®Google Scholar
• (a) Dupont , J. ; De Souza , R. F. ; Suarez , P. A. Z. Ionic liquid (molten salt) phase organometallic catalysis . Chem. Rev. 2002 , 102 , 3667 ; (b) Jain , N. ; Kumar , A. ; Chauhan , S. ; Chauhan , S. M. S. Chemical and biochemical transformations in ionic liquids . Tetrahedron 2005 , 61 , 1015 .
   PubMed Web of Science ®Google Scholar
• Wasserscheid , P. ; Keim , W. Ionic liquids—New “solutions” for transition-metal catalysis . Angew. Chem., Int. Ed. 2000 , 39 , 3773 .
   Web of Science ®Google Scholar
• Handy , S. T. Greener solvents: Room-temperature ionic liquids from biorenewable sources . Chem. Eur. J. 2003 , 9 , 2938 .
   Web of Science ®Google Scholar
• Doyle , M. ; Choi , S. K. ; Proulx , G. High-temperature proton-conducting membranes based on perfluorinated ionomer membrane–ionic liquid composites . J. Electrochem. Soc. 2000 , 147 , 34 .
   Web of Science ®Google Scholar
• Wilkes , J. S. Properties of ionic liquid solvents for catalysis . J. Mol. Catal. A 2004 , 214 , 11 .
   Web of Science ®Google Scholar
• Sotgiu , G. ; Chiarotto , I. ; Feroci , M. ; Orsini , M. ; Rossi , L. ; Inesi , A. An electrochemical alternative strategy to the synthesis of β-lactams, part 3: Room-temperature ionic liquids vs molecular organic solvents . Electrochim. Acta 2008 , 53 , 7852 .
   Web of Science ®Google Scholar
• Qi , F. ; Wang , H. Application of Prigogine–Flory–Patterson theory to excess molar volume of mixtures of 1-butyl-3-methylimidazolium ionic liquids with N-methyl-2-pyrrolidinone. J. Chem. Thermodyn. 2009, 41, 265.
   Web of Science ®Google Scholar
• Dabiri , M. ; Salehi , P. ; Baghbanzadeh , M. ; Bahramnejad , M. A facile procedure for the one-pot synthesis of unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles . Tetrahedron Lett. 2006 , 47 , 6983 .
   Web of Science ®Google Scholar
• (a) Baghbanzadeh , M. ; Salehi , P. ; Dabiri , M. ; Kozehgary , G. Water-accelerated synthesis of novel bis-2,3-dihydroquinazolin-4(1H)-one derivatives . Synthesis 2006 , 344 ; (b) Dabiri , M. ; Salehi , P. ; Mohammadi , A. ; Baghbanzadeh , M. Montmorillonite K-10–catalysed solvent-free synthesis of 2,3-disubstituted-4(3H)quinazolinones under microwave irradiation . J. Chem. Res., Synop. 2004 , 8 , 570 .
   Google Scholar
• Dabiri , M. ; Salehi , P. ; Zolfigol , M. A. ; Baghbanzadeh , M. Silica sulfuric acid as an efficient and reusable catalyst for the Pechmann synthesis of coumarins under solvent-free conditions . Heterocycles 2007 , 71 , 677 .
   Web of Science ®Google Scholar
• Dabiri , M. ; Baghbanzadeh , M. ; Arzroomchilar , E. 1-Methylimidazolium triflouroacetate ([Hmim]TFA): An efficient reusable acidic ionic liquid for the synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxo-decahydroacridines . Catal. Commun. 2008 , 9 , 939 .
   Web of Science ®Google Scholar
• Shaabani , A. ; Maleki , A. ; Behnam , M. Tandem oxidation process using ceric ammonium nitrate: Three-component synthesis of trisubstituted imidazoles under aerobic oxidation conditions . Synth. Commun. 2009 , 39 , 102 .
   Web of Science ®Google Scholar