Approach to the Synthesis of 2,3-Disubstituted-3H-quinazolin-4-ones Mediated by Ph3P-I2.

Readily available N-substituted amides or their requisite carboxylic acids or acid chlorides have been used to construct 2,3-disubstituted-3H-quinazolin-4-ones in a one-pot procedure. Key transformation in this convergent approach involves Ph3P-I2-mediated formation of amidine upon condensation of an amide or the intermediate amide with methyl anthranilate. Cyclization of the amidine-tethered anthranilate then affords 2,3-disubstituted-3H-quinazolin-4-ones in good to excellent yields under mild conditions.

[1]  M. Pattarawarapan,et al.  Ph3P/I2-mediated synthesis of N,N′-disubstituted and N,N,N′-trisubstituted amidines , 2016 .

[2]  J. Niu,et al.  A facile vanadium-catalyzed aerobic oxidative synthesis of quinazolinones from 2-aminobenzamides with aldehydes or alcohols , 2016 .

[3]  T. M. M. Maiden,et al.  Recent developments in transition metal catalysis for quinazolinone synthesis. , 2016, Organic & biomolecular chemistry.

[4]  Bin-dong Li,et al.  Iron nitrate/TEMPO-catalyzed aerobic oxidative synthesis of quinazolinones from alcohols and 2-aminobenzamides with air as the oxidant , 2016 .

[5]  A. Saeed,et al.  Quinazolines and quinazolinones as ubiquitous structural fragments in medicinal chemistry: An update on the development of synthetic methods and pharmacological diversification. , 2016, Bioorganic & medicinal chemistry.

[6]  Yalin Tang,et al.  Metal-free synthesis of quinazolinones without any additives in water , 2016 .

[7]  K. El-Bayouki,et al.  Utilization of isatoic anhydride in the syntheses of various types of quinazoline and quinazolinone derivatives , 2016 .

[8]  A. Bhavani,et al.  Kumada cross coupling reaction based synthesis, antimicrobial and computational studies of 6-aryl-2-phenyl-3-methylquinazolin-4(3H)-ones , 2016, Russian Journal of General Chemistry.

[9]  U. A. Kshirsagar,et al.  Advanced Synthetic Strategies for Constructing Quinazolinone Scaffolds , 2016, Synthesis.

[10]  Haifeng Zhou,et al.  FeCl3-catalyzed tandem condensation/intramolecular nucleophilic addition/C–C bond cleavage: a concise synthesis of 2-substitued quinazolinones from 2-aminobenzamides and 1,3-diketones in aqueous media , 2016 .

[11]  Veerababurao Kavala,et al.  Synthesis of 2,3‐Disubstituted Quinazolinone Derivatives through Copper Catalyzed C–H Amidation Reactions , 2016 .

[12]  K. Nagaiah,et al.  Rhodium(II)-Catalyzed Carbenoid Insertion of N-Tosylhydrazones into Amide NH Bonds: An Efficient Approach to N3-Benzyl/Alkyl-2-arylquinazolinones , 2016 .

[13]  Corinne Fruit,et al.  Cu/Pd-Catalyzed C-2–H Arylation of ­Quinazolin-4(3H)-ones with (Hetero)aryl Halides , 2015 .

[14]  Lei Lu,et al.  Acceptorless dehydrogenative condensation of o-aminobenzamides with aldehydes to quinazolinones in water catalyzed by a water-soluble iridium complex [Cp*Ir(H2O)3][OTf]2 , 2015 .

[15]  Haifeng Zhou,et al.  Brønsted acid-catalyzed selective C–C bond cleavage of 1,3-diketones: a facile synthesis of 4(3H)-quinazolinones in aqueous ethyl lactate , 2015 .

[16]  S. Yin,et al.  Metal- and Oxidant-Free Synthesis of Quinazolinones from β-Ketoesters with o-Aminobenzamides via Phosphorous Acid-Catalyzed Cyclocondensation and Selective C-C Bond Cleavage. , 2015, The Journal of organic chemistry.

[17]  Dinesh Kumar,et al.  Convenient synthesis of 2,3-disubstituted quinazolin-4(3H)-ones and 2-styryl-3-substituted quinazolin-4(3H)-ones: applications towards the synthesis of drugs , 2015 .

[18]  Corinne Fruit,et al.  Ligand-free Pd-catalyzed and copper-assisted C-H arylation of quinazolin-4-ones with aryl iodides under microwave heating. , 2015, Organic letters.

[19]  M. Pattarawarapan,et al.  Significance of reagent addition sequence in the amidation of carboxylic acids mediated by PPh3 and I2 , 2015 .

[20]  Xinzhong Li,et al.  One-pot solvent-free synthesis of 2, 3- disubstituted 4(3H)- quinazolinones catalyzed by long-chain double SO3H-functionalized Brønsted acidic ionic liquids under microwave irradiation , 2015, Journal of the Iranian Chemical Society.

[21]  Xuesen Fan,et al.  Rapid assembly of quinazolinone scaffold via copper-catalyzed tandem reaction of 2-bromobenzamides with aldehydes and aqueous ammonia: application to the synthesis of the alkaloid tryptanthrin , 2014 .

[22]  C. Cheon,et al.  Synthesis of quinazolinones from anthranilamides and aldehydes via metal-free aerobic oxidation in DMSO , 2014 .

[23]  G. Deng,et al.  Iron-catalyzed one-pot 2,3-diarylquinazolinone formation from 2-nitrobenzamides and alcohols. , 2013, Organic letters.

[24]  R. Cheng,et al.  One-Pot Synthesis of Quinazolinones from Anthranilamides and Aldehydes via p-Toluenesulfonic Acid Catalyzed Cyclocondensation and Phenyliodine Diacetate Mediated Oxidative Dehydrogenation , 2013 .

[25]  Yunyang Wei,et al.  Iodine-catalyzed oxidative system for cyclization of primary alcohols with o-aminobenzamides to quinazolinones using DMSO as the oxidant in dimethyl carbonate , 2013 .

[26]  Angel H. Romero,et al.  A Simple One-Pot Synthesis of 2-Substituted Quinazolin-4(3H)-ones from 2-Nitrobenzamides by Using Sodium Dithionite , 2013 .

[27]  S. Chiba,et al.  Oxidative radical skeletal rearrangement induced by molecular oxygen: synthesis of quinazolinones. , 2013, Organic letters.

[28]  Takao Saito,et al.  Functionalized Carbodiimide Mediated Synthesis of 2,3-Disubstituted Quinazolin-4(3H)-ones via the Tandem Strategy of C-Nucleophilic Addition and Intramolecular NH-Substitution Cyclization , 2012 .

[29]  Hidemasa Hikawa,et al.  Pd-catalyzed benzylic C-H amidation with benzyl alcohols in water: a strategy to construct quinazolinones. , 2012, The Journal of organic chemistry.

[30]  H. Alper,et al.  Palladium-catalyzed intermolecular cyclocarbonylation of 2-iodoanilines with N-toluenesulfonyl aldimines , 2012 .

[31]  A. Khalafi‐Nezhad,et al.  An Efficient One-Pot Accessto Quinazolinone Derivatives Using TiO2 Nanoparticlesas Catalyst: Synthesis and Vasorelaxant Activity Evaluation , 2012 .

[32]  Jianguang Zhou,et al.  Efficient syntheses of 2,3-disubstituted natural quinazolinones via iridium catalysis. , 2012, Organic & biomolecular chemistry.

[33]  Yongwen Jiang,et al.  Synthesis of 3-substituted and 2,3-disubstituted quinazolinones via Cu-catalyzed aryl amidation. , 2012, Organic letters.

[34]  M. Adib,et al.  One-Pot Three-Component Synthesisof 4(3H)-Quinazolinones from Benzyl Halides,Isatoic Anhydride, and Primary Amines , 2012 .

[35]  A. Mohammadi,et al.  KAl(SO4)2·12H2O (Alum) Catalyzed One‐Pot Three‐Component Synthesis of 2‐Alkyl and 2‐Aryl‐4(3H)‐quinazolinone under Microwave Irradiation and Solvent Free Conditions , 2011 .

[36]  Jianguang Zhou,et al.  One-pot synthesis of quinazolinones via iridium-catalyzed hydrogen transfers. , 2011, The Journal of organic chemistry.

[37]  K. Reddy,et al.  Synthesis of 3H-Quinazolin-4-ones and 4H-3,1-Benzoxazin-4-ones via Benzylic Oxidation and Oxidative Dehydrogenation using Potassium Iodide-tert-Butyl Hydroperoxide , 2011 .

[38]  M. Dabiri,et al.  A practical and versatile approach toward a one-pot synthesis of 2,3-disubstituted 4(3H)-quinazolinones , 2010 .

[39]  Xiong Huang,et al.  Theoretical study on acidities of (S)-proline amide derivatives in DMSO and its implications for organocatalysis. , 2010, The journal of physical chemistry. A.

[40]  Keith Jones,et al.  An efficient synthesis of 2,3-diaryl (3H)-quinazolin-4-ones via imidoyl chlorides , 2008 .

[41]  H. Choo,et al.  Novel quinazolinone derivatives as 5-HT7 receptor ligands. , 2008, Bioorganic & medicinal chemistry.

[42]  H. Alper,et al.  Palladium-catalyzed cyclocarbonylation of o-iodoanilines with imidoyl chlorides to produce quinazolin-4(3H)-ones. , 2008, Organic letters.

[43]  Rubén Haro,et al.  Automated liquid-liquid extraction workstation for library synthesis and its use in the parallel and chromatography-free synthesis of 2-alkyl-3-alkyl-4-(3H)-quinazolinones. , 2007, Journal of combinatorial chemistry.

[44]  U. A. Kshirsagar,et al.  Hexamethyldisilazane-iodine induced intramolecular dehydrative cyclization of diamides: a general access to natural and unnatural quinazolinones , 2007 .

[45]  A. Judkins,et al.  A novel highly stereoselective synthesis of 2,3-disubstituted 3H-quinazoline-4-one derivatives. , 2007, Organic letters.

[46]  I. Mohammadpoor‐Baltork,et al.  Bi(TFA)3–[nbp]FeCl4: a new, efficient and reusable promoter system for the synthesis of 4(3H)-quinazolinone derivatives , 2006 .

[47]  Christopher J. Wilson,et al.  Design and synthesis of a quinazolinone natural product-templated library with cytotoxic activity. , 2006, Journal of combinatorial chemistry.

[48]  M. Zolfigol,et al.  A new approach to the facile synthesis of mono- and disubstituted quinazolin-4(3H)-ones under solvent-free conditions , 2005 .

[49]  Libing Yu,et al.  Microwave-assisted one-pot synthesis of 2,3-disubstituted 3 H-quinazolin-4-ones , 2005 .

[50]  M. Dabiri,et al.  One‐Pot Synthesis of Mono‐ and Disubstituted (3H)‐Quinazolin‐4‐ones in Dry Media Under Microwave Irradiation , 2005 .

[51]  S. Xue,et al.  A facile synthesis of C2,N3-disubstituted-4-quinazolone. , 2004, The Journal of organic chemistry.

[52]  M. Dabiri,et al.  Microwave-assisted One-Pot Three Component Synthesis of Some New 4(3H)-Quinazolinone Derivatives , 2004 .

[53]  S. P. Chavan,et al.  A facile total synthesis of rutaecarpine , 2004 .

[54]  B. Snider,et al.  Amine-induced rearrangement of 4-imino-4H-3,1-benzoxazines to 4-quinazolinones Via amidine carboxamides , 2003 .

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

[56]  Y. Jahng,et al.  A facile synthesis of simple alkaloids—synthesis of 2,3-polymethylene-4(3H)-quinazolinones and related alkaloids , 2003 .

[57]  Y. Jahng,et al.  A SIMPLE SYNTHESIS OF TRYPTANTHRIN , 2003 .

[58]  M. Adib,et al.  Vinyltriphenylphosphonium salt mediated serendipitous synthesis of aryliminophosphoranes , 2002 .

[59]  S. Kuo,et al.  Antitumor agents. Part 204: synthesis and biological evaluation of substituted 2-aryl quinazolinones. , 2001, Bioorganic & medicinal chemistry letters.

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

[61]  A. Ganesan,et al.  Total synthesis of the fumiquinazoline alkaloids: solution-phase studies. , 2000, The Journal of organic chemistry.

[62]  A. Ganesan,et al.  Total Synthesis of the Quinazoline Alkaloids (-)-Fumiquinazoline G and (-)-Fiscalin B. , 1998, The Journal of organic chemistry.

[63]  K. Tamura,et al.  One-pot synthesis of trifluoroacetimidoyl halides , 1993 .

[64]  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.

[65]  F. G. Bordwell,et al.  Equilibrium Acidities in Dimethyl Sulfoxide Solution , 1988 .

[66]  A. Takada,et al.  Reaction of Triethyloxonium Fluoroborate with Acid Amide. III. Formation of Quinazoline and 4H-3, 1-Benzoxazin-4-one Derivatives , 1976 .