An efficient one-pot reaction of indoles, nitroacetate, and paraformaldehyde for the synthesis of tryptophan derivatives

被引:20
作者
Sui, Yong
Liu, Li [1 ]
Zhao, Jun-Ling
Wang, Dong
Chen, Yong-Jun
机构
[1] Chinese Acad Sci, Inst Chem, Ctr Mol Sci, Biol Chem Lab, Beijing 100080, Peoples R China
[2] Chinese Acad Sci, Grad Sch, Beijing 100080, Peoples R China
基金
中国国家自然科学基金;
关键词
tryptophan; one-pot; indole; nitroacetate;
D O I
10.1016/j.tetlet.2007.04.002
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient method for the synthesis of tryptophan analogues has been developed via one-pot reaction of commercial available indoles, ethyl nitroacetate, and paraformaldehyde in the presence of molecular sieves. The reaction provided tryptophan nitro-precursors in moderate to good yields, which were further converted to alpha-hydroxymethylated tryptophan derivatives catalyzed by DABCO in high yields. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3779 / 3782
页数:4
相关论文
共 50 条
  • [41] A simple and one-pot multi-component reaction to the synthesis of methylenebisamides
    Bagher Mohammadi
    Bahareh Rezaei Khorrami
    Monatshefte für Chemie - Chemical Monthly, 2018, 149 : 1089 - 1092
  • [42] Efficient One-Pot Synthesis of Indolhydroxy Derivatives Catalyzed by SnCl2, DFT Calculations and Docking Study
    Hakmaoui, Yassine
    Esme, Asli
    El Ajlaoui, Rahhal
    Belghiti, M. E.
    Zeroual, Abdellah
    Rakib, El Mostapha
    CHEMISTRY AFRICA-A JOURNAL OF THE TUNISIAN CHEMICAL SOCIETY, 2022, 5 (04): : 827 - 839
  • [43] Efficient Synthesis of Chloromethyl Methyl Ether and One-Pot Hydroxyl Protection
    Zheng, Dongqing
    Cao, Wei
    Ma, Haiyan
    Ding, Kai
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2016, 36 (05) : 1122 - 1126
  • [44] Ionic liquid catalyzed one-pot synthesis of spiropyran derivatives via three-component reaction in water
    Jin, Shuai-Shuai
    Ding, Mao-Hua
    Guo, Hong-Yun
    HETEROCYCLIC COMMUNICATIONS, 2013, 19 (02) : 139 - 143
  • [45] SULFAMIC ACID CATALYZED FIVE COMPONENT REACTION FOR EFFICIENT AND ONE-POT SYNTHESIS OF DENSELY FUNCTIONALIZED TETRAHYDROPYRIDINE SCAFFOLD
    Sarkate, Aniket P.
    Sangshetti, Jaiprakash N.
    Dharbale, Nanasaheb B.
    Sarkate, Ajinkya P.
    Shinde, Devanand B.
    JOURNAL OF THE CHILEAN CHEMICAL SOCIETY, 2015, 60 (01): : 2832 - 2836
  • [46] One-Pot Multicomponent Selective Synthesis of 5-Trifluoromethyl Pyrimidine Derivatives
    Lou, Dingyuan
    Ding, Yuxin
    Jin, Zhening
    Huang, Wenkai
    Shi, Yuan
    Zhang, Changjun
    Xie, Yuanyuan
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (12) : 2715 - 2720
  • [47] A One-pot Green Synthesis of Alkylidenesuccinimides
    Yan Lin
    Yang Wenguo
    Li Lixin
    Shen Yang
    Jiang Zhiyong
    CHINESE JOURNAL OF CHEMISTRY, 2011, 29 (09) : 1906 - 1910
  • [48] One-pot Synthesis of Condensed Azepines
    Bhardwaj, Khushboo
    Jaiswal, Shivangi
    Bhardwaj, Annu
    Kishore, Dharma
    Dwivedi, Jaya
    Sharma, Swapnil
    CURRENT ORGANIC CHEMISTRY, 2024, 28 (11) : 815 - 829
  • [49] One-Pot Synthesis of Polysubstituted Indoles via the Indium-Promoted Regioselective Hydrohydrazination of Terminal Alkynes
    Sakai, Norio
    Yokoyama, Takahiro
    Ishida, Kento
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2025, 14 (03)
  • [50] 3-Chlorophenylboronic acid-promoted, one-pot, aza-Friedel-Crafts reaction of indoles
    Goswami, Santosh V.
    Thorat, Prashant B.
    Shukla, Mahesh V.
    Bhusare, Sudhakar R.
    RESEARCH ON CHEMICAL INTERMEDIATES, 2015, 41 (04) : 2583 - 2589