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Synthesis of tricyclic quinazolinones via intramolecular cyclization of 3-(2-aminoalkyl)-2-(phenylamino)quinazolin-4(3H)-ones
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  • 作者:Xuhong Yang ; Minghu Wu ; Shaofa Sun ; Changfeng Huang ; Haibing Guo…
  • 关键词:Tricyclic quinazoline ; Intramolecular cyclization ; Guanidines
  • 刊名:Molecular Diversity
  • 出版年:2016
  • 出版时间:May 2016
  • 年:2016
  • 卷:20
  • 期:2
  • 页码:551-556
  • 全文大小:878 KB
  • 参考文献:1.Berlinck RGS, Burtoloso ACB, Kossuga MH (2008) The chemistry and biology of organic guanidine derivatives. Nat Prod Rep 25:919–954. doi:10.​1039/​B507874C CrossRef PubMed
    2.Cohen F, Overman LE (2001) Enantioselective total synthesis of batzelladine F: structural revision and stereochemical definition. J Am Chem Soc 123:10782–10783. doi:10.​1021/​ja017067m CrossRef PubMed
    3.Blondeau P, Segura M, Perez-Fernandez R, De Mendoza J (2007) Molecular recognition of oxoanions based on guanidinium receptors. Chem Soc Rev 36:198–210. doi:10.​1039/​B603089K CrossRef PubMed
    4.Leow D, Lin S, Chittimalla SK, Fu X, Tan CH (2008) Enantioselective protonation catalyzed by a chiral bicyclic guanidine derivative. Angew Chem 120:5723–5727. doi:10.​1002/​ange.​200801378 CrossRef
    5.Coles MP (2006) Application of neutral amidines and guanidines in coordination chemistry. Dalton Trans 8:985–1001. doi:10.​1039/​B515490A CrossRef PubMed
    6.Dalla VL, Gia O, Magno SM, Da Settimo A, Marini AM, Primofiore G, Da Settimo F, Salerno S (2001) Synthesis, in vitro antiproliferative activity and DNA-interaction of benzimidazoquinazoline derivatives as potential anti-tumor agents. Farmaco 56:159–167. doi:10.​1016/​S0014-827X(01)01079-5
    7.Chern JW, Liaw YC, Chen CS, Rong JG, Huang CL, Chan CH, Wang AHJ (1993) studies on 1,2,4-benzothiadiazine 1,1-dioxides-vii and quinazolinones-iv-synthesis of novel built-in hydroxyguanidine tricycles as potential anticancer agents. Heterocycles 36:1091–1103CrossRef
    8.Jen T, Dienel B, Bowman H, Petta J, Helt A, Loev B (1972) Amidines. 2. New class of antihypertensive agents. 1,2,3,5-Tetrahydroimidazo[2,1-b]quinazolines. J Med Chem 15:727–731. doi:10.​1021/​jm00277a008 CrossRef PubMed
    9.Lunn WHW, Harper RW, Stone RL (1971) Benzimidazo[2,1-b]quinazolin-12-ones. New class of potent immunosuppressive compounds. J Med Chem 14:1069–1071. doi:10.​1021/​jm00293a012 CrossRef PubMed
    10.Dean WD, Papadopoulos EP (1982) Synthesis of 4(3H)-quinazolinones from derivatives of methyl 2-isothiocyanatobenzoate. J Heterocycl Chem 19:1117–1124. doi:10.​1002/​jhet.​5570190527 CrossRef
    11.Larraufie MH, Ollivier C, Fensterbank L, Malacria M, Lacote E (2009) Radical synthesis of guanidines from N-Acyl cyanamides. Angew Chem Int Ed 49:2178–2181. doi:10.​1002/​anie.​200907237 CrossRef
    12.Yin P, Liu N, Deng YX, Chen Y, Deng Y, He L (2012) Synthesis of 2,4-diaminoquinazolines and tricyclic quinazolines by cascade reductive cyclization of methyl N-cyano-2-nitrobenzimidates. J Org Chem 77:2649–2658. doi:10.​1021/​jo2023697 CrossRef PubMed
    13.Yang XH, Wu MH, Sun SF, Ding MW, Xie JL, Xia QH (2008) Synthesis of 3-aminoalkyl-2-arylaminoquiazolin-4(3H)-ones and 3,3’-disubstituted bis-2-arylaminoquinazolin-4(3H)-ones via reactions of 1-aryl-3-(2-ethoxycarbonylphenyl)carbodiimides with diamines. J Heterocycl Chem 45:1365–1369. doi:10.​1002/​jhet.​5570450518 CrossRef
    14.Yang X, Wu M, Ding M (2010) Synthesis of 2,2 -disubstituted bis(3-arylquinazolin-4(3H)-one)s. Chin J Org Chem 30:1032–1038
    15.Wu MH, Hu JH, Shen DS, Bremond P, Guo H (2010) Regiospecific synthesis of 6-aryl-3-cyano-5-alkylamino/arylamino-1-p-tolyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-ones via iminophosphorane-mediated annulation. Tetrahedron 66:5112–5120. doi:10.​1016/​j.​tet.​2010.​04.​114 CrossRef
    16.Wu MH, Hu JH, Guo HB, Li Y (2012) A facile and efficient one-pot three-step protocol for synthesis of 6-aryl-7-oxo-5-aryoxy/alkoxy-1-(p-tolyl)-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidine-3-carbonitrile. Arkivoc VI:295–303
  • 作者单位:Xuhong Yang (1)
    Minghu Wu (1)
    Shaofa Sun (1)
    Changfeng Huang (2)
    Haibing Guo (1)
    Jian Wang (1)
    John Lee (3)
    Yalan Xing (3)

    1. Hubei Collaborative Innovation Centre for Non-power Nuclear Technology, College of Neuclear Technology & Chemistry and Biology, Hubei University of Science and Technology, Xianning, 437100, China
    2. Bennett Department of Chemistry, West Virginia University, Morgantown, WV, 26506, USA
    3. Department of Chemistry, William Paterson University, 300 Pompton Rd, Wayne, NJ, 07470, USA
  • 刊物类别:Chemistry and Materials Science
  • 刊物主题:Chemistry
    Analytical Chemistry
    Polymer Sciences
    Organic Chemistry
    Pharmacy
  • 出版者:Springer Netherlands
  • ISSN:1573-501X
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