p-methoxybenzyl group as a protecting group of the nitrogen in indole derivatives: Deprotection by DDQ or trifluoroacetic acid

被引:24
|
作者
Miki, Y [1 ]
Hachiken, H [1 ]
Kashima, Y [1 ]
Sugimura, W [1 ]
Yanase, N [1 ]
机构
[1] Kinki Univ, Fac Pharmaceut Sci, Higashiosaka, Osaka 577, Japan
关键词
D O I
10.3987/COM-97-7990
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Deprotection of 9-p-methoxybenzylcarbazole with DDQ gave a carbazole. However, methyl 1-p-methoxybenzylindole-2-carboxylate and dimethyl 1-p-methoxybenzyl-2,3-indoledicarboxylate were treated with TFA to yield the corresponding methyl indole-2-carboxylate and dimethyl indole-2,3-dicarboxylate.
引用
收藏
页码:1 / 4
页数:4
相关论文
共 50 条
  • [21] Development of p-phenylbenzyl as a new protecting group:: protection and deprotection of alcohols
    Sharma, GVM
    Rakesh
    TETRAHEDRON LETTERS, 2001, 42 (32) : 5571 - 5573
  • [22] Mild and efficient deprotection of the amine protecting p-methoxyphenyl (PMP) group
    Verkade, Jorge M. M.
    van Hemert, Lieke J. C.
    Quaedflieg, Peter J. L. M.
    Alsters, Paul L.
    van Delft, Floris L.
    Rutjes, Floris P. J. T.
    TETRAHEDRON LETTERS, 2006, 47 (46) : 8109 - 8113
  • [23] Optimizing the Deprotection of the Amine Protecting p-Methoxyphenyl Group in an Automated Microreactor Platform
    Koch, Kaspar
    van Weerdenburg, Bram J. A.
    Verkade, Jorge M. M.
    Nieuwland, Pieter J.
    Rutjes, Flons P. J. T.
    van Hest, Jan C. M.
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2009, 13 (05) : 1003 - 1006
  • [24] Energetic Effect of the Carboxylic Acid Functional Group in Indole Derivatives
    Carvalho, Tania M. T.
    Amaral, Luisa M. P. F.
    Morais, Victor M. F.
    Ribeiro da Silva, Maria D. M. C.
    JOURNAL OF PHYSICAL CHEMISTRY A, 2017, 121 (15): : 2980 - 2989
  • [25] A mild and efficient method for the selective cleavage of primary p-methoxybenzyl protecting group of saccharides by Co2(CO)8-Me2PhSiH-CO system
    Qian, Peng-zhan
    Yao, Wang
    Huang, Lu-bai
    Meng, Xiang-bao
    Li, Zhong-jun
    TETRAHEDRON LETTERS, 2015, 56 (37) : 5238 - 5241
  • [26] H2SO4-Silica: An Efficient Promoter for Selective Removal of Benzylidene and Isopropylidene Groups in the Presence of p-Methoxybenzyl Group
    Verma, Prashant Rajan
    Mukhopadhyay, Balaram
    JOURNAL OF CARBOHYDRATE CHEMISTRY, 2015, 34 (06) : 319 - 337
  • [27] SINGLE-STEP REMOVAL OF THE ALLYL ETHER PROTECTING GROUP WITH (PH3P)4RHH AND TRIFLUOROACETIC-ACID
    ZIEGLER, FE
    BROWN, EG
    SOBOLOV, SB
    JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11): : 3691 - 3693
  • [28] A Trifluoroacetic Acid-labile Sulfonate Protecting Group and Its Use in the Synthesis of a Near-IR Fluorophore
    Pauff, Steven M.
    Miller, Stephen C.
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (02): : 711 - 716
  • [29] Trifluoroacetic acid-mediated cleavage of a triethylsilyl protecting group: Application in the final step of the semisynthetic route to paclitaxel (Taxol)
    Singh, AK
    Weaver, RE
    Powers, GL
    Rosso, VW
    Wei, CK
    Lust, DA
    Kotnis, AS
    Comezoglu, FT
    Liu, M
    Bembenek, KS
    Phan, BD
    Vanyo, DJ
    Davies, ML
    Mathew, R
    Palaniswamy, VA
    Li, WS
    Gadamsetti, K
    Spagnuolo, CJ
    Winter, WJ
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2003, 7 (01) : 25 - 27
  • [30] Synthesis of α-glucuronic acid and amide derivatives in the presence of a participating 2-acyl protecting group
    Tosin, M
    Murphy, PV
    ORGANIC LETTERS, 2002, 4 (21) : 3675 - 3678