Ring contracting rearrangements of 3-amino-4-(arylamino)-1H-isochromen-1-ones

被引:12
|
作者
Opatz, T [1 ]
Ferenc, D [1 ]
机构
[1] Johannes Gutenberg Univ Mainz, Inst Organ Chem, D-55128 Mainz, Germany
关键词
heterocycles; amines; oxidation; ring contraction; rearrangements;
D O I
10.1002/ejoc.200500575
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two new ring contracting rearrangements of 3-amino-4-(arylamino) -1H-isochromen-1-ones, leading to 1-(arylanlino)-3-oxo-1,3-dihydroisobenzofuran-1-carboxamides and 2-aryl-3-oxo-2,3-dihydro-1H-isoindole-1-carboxamides, are described. Both conversions proceed in high yield and no further purification of the products is necessary. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006).
引用
收藏
页码:121 / 126
页数:6
相关论文
共 50 条
  • [41] Synthesis and Transformations of 5-Substituted 2-Aryl-7H-[1,2,4]triazolo[3,2-b][1,3]thiazin-7-ones and 2-Aryl-2,3-dihydro-4H-[1,3]thiazino[3,2-a]benzimidazol-4-ones
    V. N. Britsun
    A. N. Esipenko
    A. N. Chernega
    M. O. Lozinskii
    Russian Journal of Organic Chemistry, 2005, 41 : 108 - 113
  • [42] Strategic synthesis and in vitro antimicrobial evaluation of novel difluoromethylated 1-(1, 3-diphenyl-1H-pyrazol-4-yl)-3, 3-difluoro-1, 3-dihydro-indol-2-ones
    Chundawat, Tejpal Singh
    Kumari, Poonam
    Sharma, Nutan
    Bhagat, Sunita
    MEDICINAL CHEMISTRY RESEARCH, 2016, 25 (10) : 2335 - 2348
  • [43] Synthesis of Benzoxazines, Quinazolines and 4H-Benzo[e][1,3]thiazine by ANRORC Rearrangements of 1,2,4-Oxadiazoles
    Draghici, Bogdan
    El-Gendy, Bahaa El-Dien M.
    Katritzky, Alan R.
    SYNTHESIS-STUTTGART, 2012, 44 (04): : 547 - 550
  • [44] Strategic synthesis and in vitro antimicrobial evaluation of novel difluoromethylated 1-(1, 3-diphenyl-1H-pyrazol-4-yl)-3, 3-difluoro-1, 3-dihydro-indol-2-ones
    Tejpal Singh Chundawat
    Poonam Kumari
    Nutan Sharma
    Sunita Bhagat
    Medicinal Chemistry Research, 2016, 25 : 2335 - 2348
  • [45] Synthesis and Characterization of Substituted 4-Methoxy-1H-quinolin-2-ones
    Ramasamy, A. K.
    Balasubramaniam, V.
    Mohan, K.
    E-JOURNAL OF CHEMISTRY, 2010, 7 (03) : 1066 - 1070
  • [46] Synthesis of Dibenzo[ b , h ][1,5]naphthyridin-7(12 H )-ones: The Pictet-Spengler Reaction versus a Rearrangement of 4-Phenyl[1,3]oxazolo[4,5-c ]quinolines
    Shatsauskasa, Anton L.
    Kirnosov, Sergey A.
    Keyn, Ekaterina S.
    Shuvalov, Vladislav Yu.
    Kostyuchenko, Anastasia S.
    Fisyuk, Alexander S.
    SYNTHESIS-STUTTGART, 2024, 56 (13): : 2100 - 2108
  • [47] 2,3-pihydro-1H-1,3-diazepin-2-ones: synthesis and novel rearrangements into pyrrole derivatives
    Fesenko, Anastasia A.
    Shutalev, Anatoly D.
    TETRAHEDRON LETTERS, 2014, 55 (08) : 1416 - 1420
  • [48] A practical approach for preparation of 2-[(dialkylamino)-methyl]-4-aryl-2H-phthalazin-1-ones via Mannich reaction of 4-aryl-2H-phthalazin-1-ones
    Epsztajn, J
    Malinowski, Z
    Urbaniak, P
    Andrijewski, G
    SYNTHETIC COMMUNICATIONS, 2005, 35 (02) : 179 - 192
  • [49] Quinolone analogues 5.: Synthesis of 1-methylpyridazino[3,4-b]quinoxalin-4(1H)-ones
    Kurasawa, Y
    Takizawa, J
    Maesaki, Y
    Kawase, A
    Okamoto, Y
    Kim, HS
    HETEROCYCLES, 2002, 58 : 359 - 369
  • [50] New 6-amino-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines and [1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-6-ones: Synthesis, characterization and antibacterial activity evaluation
    Almajan, Gabriela Laura
    Barbuceanu, Stefania-Felicia
    Saramet, Ioana
    Draghici, Constantin
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (07) : 3191 - 3195