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
  • [1] Facile preparation of 3-amino-4-(arylamino)-1H-isochromen-1-ones by a new multicomponent reaction
    Opatz, T
    Ferenc, D
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (05) : 817 - 821
  • [2] Monocyclic 1,2,3-triazin-4(3H)-ones:: Synthesis, structure and photochemical behaviour
    Celli, Angela Maria
    Ferrini, Serena
    Ponticelli, Fabio
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (13) : 3021 - 3025
  • [3] Synthesis of 4-alkyl-1(2H)-phthalazinones and 4-alkyl-2,3-benzoxazin-1-ones via ring cleavage of 3-substituted N-alkylated-3-hydroxyisoindolin-1-ones
    Chun, TG
    Kim, KS
    Lee, S
    Jeong, TS
    Lee, HY
    Kim, YH
    Lee, WS
    SYNTHETIC COMMUNICATIONS, 2004, 34 (07) : 1301 - 1308
  • [4] Moore cyclizations: Rearrangements of 3-heteroatom-pent-1-en-4-yn-1-ones - A computational search for new reactions
    Schreiner, PR
    Bui, BH
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (05) : 1162 - 1165
  • [5] 3-(HETARYLAMINO)- AND 3-[(HETARYLMETHYL)AMINO]ISOQUINOLIN-1(2H)-ONES
    Potikha, L. M.
    Gutsul, R. M.
    Kovtunenko, V. A.
    Tolmachev, A. A.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2010, 46 (04) : 457 - 467
  • [6] Synthesis of 1,2-benzisothiazolin-3-ones by ring transformation of 1,3-benzoxathiin-4-one 1-oxides
    Shimizu, Masao
    Shimazaki, Teruaki
    Yoshida, Tetsuya
    Ando, Wataru
    Konakahara, Takeo
    TETRAHEDRON, 2012, 68 (21) : 3932 - 3936
  • [7] 3-Amino-4-[5-(chloromethyl)-1,2,4-oxadiazol-3-yl]furazan - a multifunctional synthon for the synthesis of 1,2,5-oxadiazole derivatives
    Stepanov, Andrei I.
    Dashko, Dmitry V.
    Stepanova, Elena V.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2019, 55 (12) : 1233 - 1244
  • [8] Quinoxaline-benzimidazole rearrangements in the reactions of 3-alkanoylquinoxalin-2-ones with 1,2-phenylenediamines
    Kalinin A.A.
    Isaikina O.G.
    Mamedov V.A.
    Chemistry of Heterocyclic Compounds, 2007, 43 (10) : 1307 - 1314
  • [9] 3-Amino-4-[5-(chloromethyl)-1,2,4-oxadiazol-3-yl]furazan –a multifunctional synthon for the synthesis of 1,2,5-oxadiazole derivatives
    Andrei I. Stepanov
    Dmitry V. Dashko
    Elena V. Stepanova
    Chemistry of Heterocyclic Compounds, 2019, 55 : 1233 - 1244
  • [10] Synthesis of new 1,5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-ones under catalyst-free and solvent-free conditions
    Niknam, Khodabakhsh
    Mojikhalifeh, Sanaz
    MOLECULAR DIVERSITY, 2014, 18 (01) : 111 - 117