Synthesis of 1-Substituted 4(1H)-Quinazolinones Under Solvent-Free Conditions

REFERENCES

• Kempis , I. M. ; Islam , K. ; Then , R. L. DNA and RNA synthesis: Antifolates . Chem. Rev. 2005 , 105 , 593 – 620 .
   PubMed Web of Science ®Google Scholar
• Mahaska , S. B. ; Argade , N. P. The chemistry of recently isolated naturally occurring quinazolinone alkaloids . Tetrahedron 2006 , 62 , 9787 – 9826 .
   Web of Science ®Google Scholar
• Connolly , D. J. ; Cusack , D. ; O'Sullivan , T. P. ; Guiry , P. J. Synthesis of quinazolinones and quinazolines. Tetrahedron 2005, 61, 10153–10202.
   Web of Science ®Google Scholar
• Pakrashi , S. C. ; Bhattacharyya , J. Studies on Indian medicinal plants. IV. Further alkaloids from Glycosmis arborea . J. Sci. Industr. Res. 1962 , 21B , 49 – 50 .
   Google Scholar
• Maillard , J. ; Benard , M. ; Vincent , M. ; Vo-Van-Tri ; Jolly , R. ; Morin , R. ; Benharkate , M. ; Menillet , C. (3H)-Quinazolin-4-one derivatives with anti-inflammatory activity, II: Derivatives substituted in the aromatic nucleus and related compounds . Chim. Ther. 1967 , 2 , 231 – 239 .
   Google Scholar
• Vincent , M. ; Poignant , J.-C. ; Remond , G. 2-(Alkenylamino)benzamides and related 1-(alkenyl)-4(1H)-quinazolinones as analgetics and anti-inflammatories . J. Med. Chem. 1971 , 14 , 714 – 717 .
   Web of Science ®Google Scholar
• Somasekhara , S. ; Shah , G. M. ; Mukherjee , S. L. N-Substituted 1,4-dihydroquinazolin-4-ones . Curr. Sci. 1964 , 33 , 521 – 521 .
   Web of Science ®Google Scholar
• Leonard , N. J. ; Ruyle , W. V. Reactions of 4(1H)-quinazolone, IV: Replacements at the 3-position . J. Org. Chem. 1948 , 13 , 903 – 910 .
   PubMed Web of Science ®Google Scholar
• Kametani , T. ; Loc , C. V. ; Higa , T. ; Ihara , M. ; Fukumoto , K. Studies on the syntheses of heterocyclic compounds, part 724: Total syntheses of the quinazolinone alkaloids glycorine, glomerine, homoglomerine, crysogine, and euxylophoricines A and C . J. Chem. Soc., Perkin Trans. 1 1977 , 21 , 2347 – 2349 .
   Google Scholar
• Rad-Moghadam , K. ; Mohseni , M. An expeditious and solvent-free route to the synthesis of 2-substituted quinazolin-4(3H)-ones under microwave conditions . J. Chem. Res., Synop. 2003 , 6 , 487 – 488 ..
   Google Scholar
• Hughes , L. R. ; Jackman , A. L. ; Oldfield , J. ; Smith , R. C. ; Burrows , K. D. ; Marsham , P. R. ; Bishop , J. A. M. ; Jones , T. R. ; O'Connor , B. M. ; Calvert , A. H. Quinazoline antifolate thymidylate synthase inhibitors: Alkyl, substituted alkyl, and aryl substituents in the C-2 position . J. Med. Chem. 1990 , 33 , 3060 – 3067 .
   PubMed Web of Science ®Google Scholar
• Bavetsias , V. ; Jackman , A. L. ; Kimbell , R. ; Gibson , W. ; Boyle , F. T. ; Bisset , G. M. F. Quinazoline antifolate thymidylate synthase inhibitors: γ-Linked L-D, D-D, and D-L dipeptide analogues of 2-desamino-2-methyl-N 10-propargyl-5,8-dideazafolic acid (ICI 198583) . J. Med. Chem. 1996 , 39 , 73 – 85 .
   PubMed Web of Science ®Google Scholar
• (a) Cao , S. ; Feng , Y. ; Zheng , X. ; Jiang , Y. ; Zhang , M. ; Wang , Y. ; Xu , M. Synthesis of substituted benzylamino- and heterocyclylmethylamino-carbodithioate derivatives of 4(3H)-quinazolinone and their cytotoxic activity . Arch. Pharm. 2006 , 339 , 250 – 254 (b) Cao , S. ; Wang , Y. ; Zhu , L. ; Liao , J. ; Guo , Y. ; Chen , L. ; Liu , H. ; Xu , X. Synthesis and cytotoxic activity of N-((2-methyl-4(3H)-quinazolinon-6-yl)methyl)dithiocarbamates . Eur. J. Med. Chem. 2010 , 45 , 3850 – 3857 .
   PubMed Web of Science ®Google Scholar
• Süsse , M. ; Johne , S. Quinazoline carboxylic acids, 5: 1,4-Dihydroquinazoline-4-on-l-ylacetic acids and esters . Monatsh. Chem. 1986 , 117 , 499 – 509 .
   Web of Science ®Google Scholar
• Nikpour , F. ; Paibast , T. A green, facile, and one-pot synthesis of 1,4-(1H,3H)-quinazolinediones under microwave irradiations . Chem. Lett. 2005 , 34 , 1438 – 1439 .
   Web of Science ®Google Scholar
• Cao , S. ; Ma , X. Synthesis of 6-bromomethyl-3,4-dihydro-2-methyl-4-oxoquinazoline . Huaxue Shiji 2004 , 26 , 27 – 28 .
   Google Scholar
• Wakae , M. ; Konishi , K. Synthesis of alkylanthranilic acid by reductive alkylation . J. Soc. Org. Synth. Chem. 1953 , 11 , 434 – 436 .
   Google Scholar
• Unangst , P. C. ; Brown , R. E. ; Fabian , A. ; Fontsere , F. 2-Indolyl ketone synthesis . J. Heterocycl. Chem. 1979 , 16 , 661 – 666 .
   Web of Science ®Google Scholar