Synthesis of 5-alkoxy-4-alkylamino-1,2-benzoquinones

被引：0
|
作者：
Viallon, L
Reinaud, O
Capdevielle, P
Maumy, M
机构：
来源：
SYNTHESIS-STUTTGART | 1995年 / 12期
关键词：
1,2-benzoquinones; aminoquinones; nucleophilic substitution by amines; regioselectivity;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple and efficient method is described for a general synthesis of 4-dialkylamino-5-methoxy-1,2-benzoquinones 3 which involves, in polar solvents, a regioselective (> 95 %) nucleophilic monosubstitution by a wide range of secondary aliphatic amines on an easily prepared 1,2-quinone 1. Regioselectivity is not observed in the reaction of primary amines with 1, but a further reaction with an alcohol in basic medium allows valorization of the undesirable product.
引用
收藏
页码：1534 / +
页数：1
相关论文
共 50 条
  • [1] SYNTHESIS OF HALODIMETHOXY-1,2-BENZOQUINONES
    WRIEDE, U
    FERNANDEZ, M
    WEST, KF
    HARCOURT, D
    MOORE, HW
    JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (20): : 4485 - 4489
  • [2] SYNTHESIS OF TETRAHYDROAZOCINO-1,2-BENZOQUINONES AND DIHYDROAZEPINO-1,2-BENZOQUINONES VIA AMINO-CLAISEN REARRANGEMENT OF 4-(2-VINYL-AZETIDINO AND AZIRIDINO)-1,2-BENZOQUINONES
    VIALLON, L
    REINAUD, O
    CAPDEVIELLE, P
    MAUMY, M
    TETRAHEDRON LETTERS, 1995, 36 (27) : 4787 - 4790
  • [3] SYNTHESIS OF VINYLKETENES - THERMOLYSIS OF 3-AZIDO-1,2-BENZOQUINONES
    DORSEY, DA
    KING, SM
    MOORE, HW
    JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (14): : 2814 - 2816
  • [4] Routes of π-Electron Delocalization in 4-Substituted-1,2-benzoquinones
    Szatylowicz, Halina
    Krygowski, Tadeusz M.
    Palusiak, Marcin
    Poater, Jordi
    Sola, Miquel
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (02): : 550 - 556
  • [5] REACTION OF 1,2-BENZOQUINONES WITH ENAMINES
    OMOTE, Y
    TOMOTAKE, A
    KASHIMA, C
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (02): : 151 - 156
  • [6] Synthesis of tetrahydroazocino- and dihydroazepino-1,2-benzoquinones via amino-Claisen rearrangement of 4-(2-vinyl-azetidino and aziridino)-1,2-benzoquinones
    Viallon, L.
    Reinaud, O.
    Capdevielle, P.
    Maumy, M.
    Tetrahedron Letters, 1995, 36 (27):
  • [7] REDOX POTENTIAL OF SUBSTITUTED 4,5-METHYLENEDIOXY-1,2-BENZOQUINONES
    DALLACKER, F
    LOHNERT, G
    KIM, I
    CHEMISCHE BERICHTE-RECUEIL, 1974, 107 (07): : 2415 - 2417
  • [8] DFT studies of the toxicity of 4-substituted 1,2-benzoquinones
    Steklac, Marek
    Breza, Martin
    POLYHEDRON, 2021, 210
  • [9] DIMERIZATION PRODUCTS OF SUBSTITUTED 1,2-BENZOQUINONES
    WATSON, WH
    NAGL, A
    STEGLICH, W
    EBERT, B
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1988, 44 : 2178 - 2182
  • [10] One-pot preparation of 4,5-disubstituted-1,2-benzoquinones
    Zhang, XC
    Huang, ZS
    Wei, HF
    Wang, ZC
    Ma, L
    Gu, LQ
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 1999, 19 (02) : 200 - 203
12345