Highly efficient copper-catalyzed cascade synthesis of quinazoline and quinazolinone derivatives.

We have developed a general and highly efficient copper-catalyzed method for synthesis of quinazoline and quinazolinone derivatives, the target products were obtained in good to excellent yields via cascade reactions of amidine hydrochlorides with substituted 2-halobenzaldehydes, 2-halophenylketones, or methyl 2-halobenzoates, and the method is of simple, economical and practical advantages.

[1]  G. Evano,et al.  Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis. , 2008, Chemical reviews.

[2]  Hua Fu,et al.  A mild and efficient method for copper-catalyzed ullmann-type N-arylation of aliphatic amines and amino acids , 2007 .

[3]  D. Ma,et al.  Synthesis of 1,2-disubstituted benzimidazoles by a Cu-catalyzed cascade aryl amination/condensation process. , 2007, Angewandte Chemie.

[4]  Yuyang Jiang,et al.  CuBr/rac-BINOL-catalyzed N-arylations of aliphatic amines at room temperature. , 2007, The Journal of organic chemistry.

[5]  N. Argade,et al.  The Chemistry of Recently Isolated Naturally Occurring Quinazolinone Alkaloids , 2006 .

[6]  Xun Guo,et al.  An Inexpensive and Efficient Copper Catalyst for N‐Arylation of Amines, Amides and Nitrogen‐Containing Heterocycles , 2006 .

[7]  S. Moro,et al.  Structural investigation of the 7-chloro-3-hydroxy-1H-quinazoline-2,4-dione scaffold to obtain AMPA and kainate receptor selective antagonists. Synthesis, pharmacological, and molecular modeling studies. , 2006, Journal of medicinal chemistry.

[8]  Stuart C. Wilson,et al.  Targeting the alpha-folate receptor with cyclopenta[g]quinazoline-based inhibitors of thymidylate synthase. , 2006, Bioorganic & medicinal chemistry.

[9]  Yuyang Jiang,et al.  A versatile and efficient ligand for copper-catalyzed formation of C-N, C-O, and P-C bonds: pyrrolidine-2-phosphonic acid phenyl monoester. , 2006, Chemistry.

[10]  D. Ma,et al.  Mild Ullmann-type biaryl ether formation reaction by combination of ortho-substituent and ligand effects. , 2006, Angewandte Chemie.

[11]  J. Ellman,et al.  Rhodium-catalyzed direct C-H addition of 3,4-dihydroquinazolines to alkenes and their use in the total synthesis of vasicoline. , 2006, The Journal of organic chemistry.

[12]  P. Guiry,et al.  Synthesis of Quinazolinones and Quinazolines , 2005 .

[13]  T. Nomura,et al.  Luotonin A: A Lead toward Anti-Cancer Agent Development , 2005 .

[14]  Yuyang Jiang,et al.  Copper-catalyzed arylation of amines using diphenyl pyrrolidine-2-phosphonate as the new ligand. , 2005, The Journal of organic chemistry.

[15]  Libing Yu,et al.  Three-component one-pot total syntheses of glyantrypine, fumiquinazoline F, and fiscalin B promoted by microwave irradiation. , 2005, The Journal of organic chemistry.

[16]  Christopher J. Wilson,et al.  Novel one-pot total syntheses of deoxyvasicinone, mackinazolinone, isaindigotone, and their derivatives promoted by microwave irradiation. , 2005, Organic Letters.

[17]  I. Beletskaya,et al.  Copper in cross-coupling reactions: The post-Ullmann chemistry , 2004 .

[18]  J. Chern,et al.  Nucleosides XI. Synthesis and antiviral evaluation of 5'-alkylthio-5'-deoxy quinazolinone nucleoside derivatives as S-adenosyl-L-homocysteine analogs. , 2004, Chemical & pharmaceutical bulletin.

[19]  Ying Han,et al.  Efficient synthesis of 4-aminoquinazoline and thieno[3,2-d]pyrimidin-4-ylamine derivatives by microwave irradiation. , 2004, Organic letters.

[20]  M. Marschall,et al.  Novel Chemical Class of pUL97 Protein Kinase-Specific Inhibitors with Strong Anticytomegaloviral Activity , 2004, Antimicrobial Agents and Chemotherapy.

[21]  P. S. Leventhal,et al.  Synthesis of AX7593, a quinazoline-derived photoaffinity probe for EGFR. , 2004, Organic letters.

[22]  A. Kamal,et al.  Microwave enhanced reduction of nitro and azido arenes to N-arylformamides employing Zn–HCOONH4: synthesis of 4(3H)-quinazolinones and pyrrolo[2,1-c][1,4]benzodiazepines , 2004 .

[23]  C. Massera,et al.  Synthesis of 4H-3,1-benzoxazines, quinazolin-2-ones, and quinoline-4-ones by palladium-catalyzed oxidative carbonylation of 2-ethynylaniline derivatives. , 2004, The Journal of organic chemistry.

[24]  Artis Klapars,et al.  Synthesis of medium ring nitrogen heterocycles via a tandem copper-catalyzed C-N bond formation-ring-expansion process. , 2004, Journal of the American Chemical Society.

[25]  C. Bailly,et al.  Synthesis of condensed quinolines and quinazolines as DNA ligands. , 2004, Bioorganic & medicinal chemistry.

[26]  P. Plé,et al.  Discovery of a new class of anilinoquinazoline inhibitors with high affinity and specificity for the tyrosine kinase domain of c-Src. , 2004, Journal of medicinal chemistry.

[27]  U. Scholz,et al.  Renaissance of Ullmann and Goldberg Reactions - Progress in Copper Catalyzed C-N-, C-O- and C-S-Coupling , 2003 .

[28]  S. Ley,et al.  Modern Synthetic Methods for Copper‐Mediated C(aryl) ? O, C(aryl) ? N, and C(aryl) ? S Bond Formation , 2003 .

[29]  L. Doyle,et al.  Multidrug resistance mediated by the breast cancer resistance protein BCRP (ABCG2) , 2003, Oncogene.

[30]  P. Forster,et al.  Alkaloids and limonoids from Bouchardatia neurococca: systematic significance. , 2003, Phytochemistry.

[31]  J. Bergman,et al.  Recent Developments in the Field of Quinazoline Chemistry , 2003 .

[32]  A. Lewerenz,et al.  A3 receptors in cortical neurons: Pharmacological aspects and neuroprotection during hypoxia , 2003 .

[33]  J Kaustová,et al.  Influence of the replacement of the oxo function with the thioxo group on the antimycobacterial activity of 3-aryl-6,8-dichloro-2H-1,3-benzoxazine-2,4(3H)-diones and 3-arylquinazoline-2,4(1H,3H)-diones. , 2001, Farmaco.

[34]  J. Kuneš,et al.  Quinazoline derivatives with antitubercular activity. , 2000, Farmaco.

[35]  Alper,et al.  Palladium-catalyzed cyclocarbonylation of o-iodoanilines with heterocumulenes: regioselective preparation of 4(3H)-quinazolinone derivatives , 2000, The Journal of organic chemistry.

[36]  K. Nicolaou,et al.  New Synthetic Technology for the Synthesis of Aryl Ethers: Construction of C-O-D and D-O-E Ring Model Systems of Vancomycin , 1997 .

[37]  T. Nomura,et al.  TWO NEW PYRROLOQUINAZOLINOQUINOLINE ALKALOIDS FROM PEGANUM NIGELLASTRUM , 1997 .

[38]  T. Aoyagi,et al.  Production of 2-methyl-4[3H]-quinazolinone, an inhibitor of poly(ADP-ribose) synthetase, by bacterium. , 1991, The Journal of antibiotics.