A CONVENIENT SYNTHESIS OF 2-ALKYL-MONO-O-ALKYLATED AND 2-ALKYL RESORCINOLS

被引：16
|
作者：
STEALEY, MA
SHONE, RL
MIYANO, M
机构：
[1] Dept. of Medicinal Chemistry., G. D. Searle and Co., Skokie, Illinois
来源：
SYNTHETIC COMMUNICATIONS | 1990年 / 20卷 / 12期
关键词：
D O I：
10.1080/00397919008053113
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The title C,O -dialkylated resorcinols have seldom been prepared. We have developed a practical synthesis of this class of compounds starting with cyclohexane-1,3-dione. The key features of the synthesis are mono-O-alkylation of a 2-alkyl cyclohexane-1,3-dione and Pd-C catalyzed or NBS/DBU aromatization of the resultant O-alkyl-2-alkyl cyclohexane-1,3-dione. The use of cyclohexane-1,3-dione allows regioselective alkylations that would not be possible with resorcinol itself. A convenient synthesis of 2-alkyl resorcinols from cyclohexane-1,3-dione has also been achieved. © 1990, Taylor & Francis Group, LLC. All rights reserved.
引用
收藏
页码：1869 / 1876
页数：8
相关论文
共 50 条
  • [1] Synthesis of 2-alkyl(aryl)thietanes
    N. P. Volynskii
    S. E. Shevchenko
    Petroleum Chemistry, 2007, 47 (2) : 109 - 117
  • [2] Convenient syntheses of 2-alkyl(aryl)-4,5-diphenyloxazoles and 2-alkyl(aryl)-4-phenyloxazoles
    Pei, WW
    Li, SH
    Nie, XP
    Li, YW
    Pei, J
    Chen, BZ
    Wu, J
    Ye, XL
    SYNTHESIS-STUTTGART, 1998, (09): : 1298 - 1304
  • [3] Synthesis of 2-alkyl(aryl)thietanes
    Volynskii, N. P.
    Shevchenko, S. E.
    PETROLEUM CHEMISTRY, 2007, 47 (02) : 109 - 117
  • [4] Microwave assisted one pot synthesis of 2-alkyl amino benzimidazoles, 2-alkyl amino benzoxazoles and 2-alkyl amino benzthiazoles by using various carbodiimides
    Rapolu, Thirupathi
    Naveen, Polkam
    Kumar, K. V. P. Pavan
    Leleti, Krishnakanth Reddy
    Korapolu, Raghubabu
    RESULTS IN CHEMISTRY, 2022, 4
  • [5] ENANTIOSELECTIVE SYNTHESIS OF 2-ALKYL SUBSTITUTED CYSTEINES
    PATTENDEN, G
    THOM, SM
    JONES, MF
    TETRAHEDRON, 1993, 49 (10) : 2131 - 2138
  • [6] Synthesis and pharmacology of 2-alkyl raloxifene analogs
    Grese, TA
    Cho, S
    Bryant, HU
    Cole, HW
    Glasebrook, AL
    Magee, DE
    Phillips, DL
    Rowley, ER
    Short, LL
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (02) : 201 - 206
  • [7] GENERAL SYNTHESIS OF 2-ALKYL TETRONIC ACIDS
    DAMON, RE
    LUO, T
    SCHLESSINGER, RH
    TETRAHEDRON LETTERS, 1976, (32) : 2749 - 2752
  • [8] Synthesis of 2-alkyl triazoles with solvothermal conditions
    Ma, Youcai
    Zhang, Xiaohui
    Yang, Yawen
    Hu, Liangzhen
    Xiong, Yan
    TETRAHEDRON, 2022, 113
  • [9] Synthesis and characterization of (N→B) phenyl[N-alkyl-N-(2-alkyl) aminodiacetate-O,O′,N]boranes and phenyl[N-alkyl-N-(2-alkyl) aminodiacetate-O,O′,N]boranes
    Mancilla, Teresa
    Calixto Romo, Maria de los Angeles
    Amaya Delgado, Lorena
    POLYHEDRON, 2007, 26 (05) : 1023 - 1028
  • [10] A NEW SYNTHESIS OF 2-ALKYL AND 2-ACYL KETONES
    STORK, G
    TERRELL, R
    SZMUSZKOVICZ, J
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (07) : 2029 - 2030
12345