Synthesis of Novel 1,4-Benzoxazine-2,3-Dicarboximides from Maleic Anhydride and Substituted Aromatic Amines

REFERENCES

• Achari , B. ; Mandal , S. B. ; Dutta , P. K. ; Chowdhury , P. C. Perspectives on 1,4-benzodioxins, 1,4-benzoxazines and their 2,3-dihydro derivatives . Synlett. 2004 , 14 , 2449 – 2467 .
   Google Scholar
• Iakovou , K. ; Kazanis , M. ; Vavayannis , A. ; Bruni , G. ; Romeo , M. R. ; Massarelli , P. ; Teramoto , S. ; Fujiki , H. ; Mori , T. Synthesis of oxypropanolamine derivatives of 3,4-dihydro-2H-1,4-benzoxazine, β-adrenergic affinity, inotropic, chronotropic and coronary vasodilating activities . Eur. J. Med. Chem. 1999 , 34 , 903 – 917 .
   PubMedGoogle Scholar
• Nicolaides , D. N. ; Gautam , D. R. ; Litinas , K. E. ; Hadjipavlou-Litina , D. J. ; Kontogiorgis , C. A. Synthesis and biological evaluation of benzo[7,8]chromeno[5,6-b][1,4]oxazin-3-ones. J. Heterocyclic Chem. 2004, 41, 605–611.
   Google Scholar
• Touzeau , F. ; Arrault , A. ; Guillaumet , G. ; Scalbert , E. ; Pfeiffer , B. ; Rettori , M-C. : Renard , P. ; Merour , J.-Y. Synthesis and biological evaluation of new 2-(4,5-dihydro-1H-imidazol-2-yl)-3,4-dihydro-2H-1,4-benzoxazine derivatives . J. Med. Chem. 2003 , 46 , 1962 – 1979 .
   PubMed Web of Science ®Google Scholar
• Jiao , P.-F. ; Zhao , B.-X. ; Wang , W.-W. ; He , Q.-X. ; Wan , M.-S. ; Shin , D.-S. ; Miao , J.-Y. Design, synthesis, and preliminary biological evaluation of 2,3-dihydro-3-hydroxymethyl-1,4-benzoxazine derivatives . Bioorg. Med. Chem. Lett. 2006 , 16 , 2862 – 2867 .
   PubMed Web of Science ®Google Scholar
• Macchiarulo , A. ; Costantino , G. ; Fringuelli , D. ; Vecchiarelli , A. ; Schiaffella , F. ; Fringuelli , R. 1,4-benzothiazine and 1,4-benzoxazne imidazole derivatives with antifungal activity : A docking study . Bioorg. Med. Chem. 2002 , 10 , 3415 – 3423 .
   PubMed Web of Science ®Google Scholar
• Mashevskaya , I. V. ; Tolmacheva , I. A. ; Voronova , E. V. ; Odegova , T. F. ; Aleksandrova , G. A. ; Goleneva , A. F. ; Kol' tsova , S. V. ; Maslivets , A. N. A comparative study of the antimicrobial activity of some quinoxalines, 1,4-benzoxazines, and aza-analogs . Pharm. Chem. J. 2002 , 36 , 86 – 88 .
   Google Scholar
• Alper-Hayta , S. ; Aki-Sener , E. ; Tekiner-Gulbas , B. ; Yildiz , I. ; Temiz-Arpaci , O. ; Yalcin , I. ; Altanlar , N. Synthesis, antimicrobial activity and OSARs of new benzoxazine-3-ones . Eur. J. Med. Chem. 2006 , 41 , 1398 .
   PubMed Web of Science ®Google Scholar
• Macias , F. A. ; Marin , D. ; Oliveros-Bastidas , A. ; Castellano , D. ; Simonet , A. M. ; Molinillo , J. M. G. Structure–activity relationship studies of benzoxazinones and related compounds. Phytotoxicity on Echinochloa crus-galli (L.) P. Beauv . J. Agric. Food Chem. 2005 , 53 , 538 – 548 .
   PubMed Web of Science ®Google Scholar
• Chioccara , F. ; Prota , G. ; Thomson , R. H. New benzoxazine and benzothiazine dyes . Tetrahedron. 1976 , 32 , 1407 – 1409 .
   Web of Science ®Google Scholar
• Hassan , G. S. Synthesis and pharmacological evaluation of certain furo-1,3-benzoxazole and furo-1,4-benzoxazine derivatives as analgesic, antipyretic, and anti-inflammatory agents . Alexandria J. Pharm. Sci. 2004 , 18 , 129 – 137 .
   Google Scholar
• Blattes , E. ; Lockhart , B. ; Lestage , P. ; Schwendimann , L. ; Gressens , P. ; Fleury , M.-B. ; Largeron , M. Novel 2-alkylamino-1,4-benzoxazine derivatives as potent neuroprotective agents: Structure-activity relationship studies . J. Med. Chem. 2005 , 48 , 1282 – 1286 .
   PubMedGoogle Scholar
• Largeron , M. ; Mesples , B. ; Gressens , P. ; Cecchelli , R. ; Spedding , M. ; Le Ridant , A. ; Fleury , M.-B. The neuroprotective activity of 8-alkylamino-1,4-benzoxazine antioxidants . Eur. J. Pharmacol. 2001 , 424 , 189 – 194 .
   PubMed Web of Science ®Google Scholar
• Breznik , M. ; Mrcina , A. ; Kikelj , D. Enatioselective synthesis of (R)- and (S)-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxamides . Tetrahedron: Asymmetry. 1998 , 9 , 1115 – 1116 .
   Google Scholar
• Chen , X. L. ; Zheng , Y. G. ; Shen , Y. C. Natural products with maleic anhydride structure: Nonadrides, Tautomycin, Chaetomellic anhydride, and other compounds . Chem. Rev. 2007 , 107 , 1777 – 1830 .
   PubMed Web of Science ®Google Scholar
• Pompe , T. ; Renner , L. ; Grimmer , M. ; Herold , N. ; Werner , C. Functional films of maleic anhydride copolymers under physiological conditions. Macromol. Biosci. 2005, 5, 890–895.
   PubMed Web of Science ®Google Scholar
• Hao , X. J. ; Stenzel , M. H. ; Barner-Kowollik , C. ; Davis , T. P. ; Evans , E. Molecular composite materials formed from block copolymers containing a side-chain liquid crystalline segment and an amorphous styrene/maleic anhydride segment . Polymer. 2004 , 45 , 7401 – 7415 .
   Web of Science ®Google Scholar
• Halim , D. ; Caron , K. ; Keillor , J. W. Synthesis and evaluation of peptidic maleimides as transglutaminase inhibitors . Bioorg. Med. Chem. Lett. 2007 , 17 , 305 – 308 .
   PubMedGoogle Scholar
• Le , S. C. Maleimide spacers as versatile linkers in the synthesis of bioconjugates of anthracyclines . Nat. Prod. Rep. 2006 , 23 , 357 – 367 .
   PubMedGoogle Scholar
• Gaina , C. Synthesis and characterization of new comounds containing 1,4-dithiintetra-carboxydiimide units . Rev. Roum. Chim. 2005 , 50 , 601 – 607 .
   Google Scholar
• Mao , Y. Q. ; Maley , L. ; Waston , W. H. Syntheses and structures of N-phenylmaleimide-triazoles and by-products . J. Chem. Crystallogr. 2005 , 35 , 385 – 403 .
   Google Scholar
• Hayakawa , H. ; Nanya , S. ; Yamamoto , T. ; Maekawa , E. ; Ueno , Y. Synthesis of 1- and 4-substituted 5H-benzo[a]phenoxazin-5-ones . J. Heterocycl. Chem. 1986 , 23 , 1737 – 1740 .
   Google Scholar
• Ueno , Y. ; Maeda , K. ; Koshitani , J. ; Yoshida , T. The photochemical reactions of 5H-benzo[a]phenothiazin-5-one with alkylthiols and thiophenol . J. Heterocycl. Chem. 1982 , 19 , 189 – 191 .
   Google Scholar
• Agarwal , N. L. ; Schaefer , W. Quinone chemistry: Reaction of 2,3-dichloro-1,4-naphthoquinone with 2-aminophenols in pyridine . J. Org. Chem. 1980 , 45 , 5144 – 5149 .
   Google Scholar
• Augustin , M. ; Schneider , B. ; Koehler , M. Reaction of 2,3-dichloromaleimides with ethyoxycarbonylmethylenetriphenylphosphorane and secondary reactions . J. Prakt. Chemie (Leipzig). 1976 , 321 , 797 – 803 .
   Google Scholar