One-pot synthesis of tryptanthrin by the Dakin oxidation of indole-3-carbaldehyde

被引:40
作者
Abe, Takumi [1 ]
Itoh, Tomoki [1 ]
Choshi, Tominari [2 ]
Hibino, Satoshi [2 ]
Ishikura, Minoru [1 ]
机构
[1] Hlth Sci Univ Hokkaido, Sch Pharmaceut Sci, Ishikari, Hokkaido 0610293, Japan
[2] Fukuyama Univ, Fac Pharm & Pharmaceut Sci, Fukuyama, Hiroshima 7290292, Japan
关键词
Oxidative coupling; Indole-3-carbaldehyde; Indolo[2,1-b]quinazoline; Urea hydrogen peroxide; Dakin oxidation; DERIVATIVES; CANDIDINE; ALKALOIDS; INDOLES; ANALOGS; AGENTS;
D O I
10.1016/j.tetlet.2014.07.113
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A one-pot approach to indolo[2,1-b]quinazolines from indole-3-carbaldehydes through the Dakin oxidation was developed. It was shown that the reaction proceeded through the condensation of indole-3-carbaldehydes with isatoic anhydrides, derived in situ from indole-3-carbaldehydes by the Dakin oxidation, and further oxidation/cyclization steps. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5268 / 5270
页数:3
相关论文
共 28 条
  • [1] Concise Total Synthesis of Calothrixins A and B
    Abe, Takumi
    Ikeda, Toshiaki
    Yanada, Reiko
    Ishikura, Minoru
    [J]. ORGANIC LETTERS, 2011, 13 (13) : 3356 - 3359
  • [2] Synthesis of 4,7-indoloquinones from indole-7-carbaldehydes by Dakin oxidation
    Alamgir, Mahiuddin
    Mitchell, Peter S. R.
    Bowyer, Paul K.
    Kumar, Naresh
    Black, David StC.
    [J]. TETRAHEDRON, 2008, 64 (30-31) : 7136 - 7142
  • [3] Electrosynthesis of tryptanthrin
    Batanero, Belen
    Barba, Fructuoso
    [J]. TETRAHEDRON LETTERS, 2006, 47 (47) : 8201 - 8203
  • [4] THE IDENTITY OF CANDIDINE AND QINGDAINONE
    BERGMAN, J
    [J]. PHYTOCHEMISTRY, 1989, 28 (12) : 3547 - 3547
  • [5] STRUCTURE DETERMINATION OF CANDIDINE, A VIOLET INDOLIC CONSTITUENT FROM CULTURE SOLUTIONS OF CANDIDA-LIPOLYTICA
    BERGMAN, J
    TILSTAM, U
    [J]. TETRAHEDRON, 1985, 41 (14) : 2883 - 2884
  • [6] I2/TBHP-Catalyzed Chemoselective Amination of Indoles
    Cai, Zhong-Jian
    Wang, Shun-Yi
    Ji, Shun-Jun
    [J]. ORGANIC LETTERS, 2013, 15 (20) : 5226 - 5229
  • [7] Alkaloids from the Root of Isatis indigotica
    Chen, Minghua
    Gan, Lishe
    Lin, Sheng
    Wang, Xiaoliang
    Li, Li
    Li, Yuhuan
    Zhu, Chenggen
    Wang, Yanan
    Jiang, Bingya
    Jiang, Jiandong
    Yang, Yongchun
    Shi, Jiangong
    [J]. JOURNAL OF NATURAL PRODUCTS, 2012, 75 (06): : 1167 - 1176
  • [8] Total Synthesis of a Pyrroloindoloquinazoline Alkaloid
    Gahtory, Digvijay
    Chouhan, Mangilal
    Sharma, Ratnesh
    Nair, Vipin A.
    [J]. ORGANIC LETTERS, 2013, 15 (15) : 3942 - 3945
  • [9] Design, Synthesis, and Structure-Activity Relationship Studies of Tryptanthrins As Antitubercular Agents
    Hwang, Jae-Min
    Oh, Taegwon
    Kaneko, Takushi
    Upton, Anna M.
    Franzblau, Scott G.
    Ma, Zhenkun
    Cho, Sang-Nae
    Kim, Pilho
    [J]. JOURNAL OF NATURAL PRODUCTS, 2013, 76 (03): : 354 - 367
  • [10] One-pot synthesis of simple alkaloids: 2,3-polymethylene-4(3H)-quinazolinones, luotonin A, tryptanthrin, and rutaecarpine
    Jahng, Katherine Chae
    Kim, Seung Ill
    Kim, Dong Hyeon
    Seo, Chang Seob
    Son, Jong-Keun
    Lee, Seung Ho
    Lee, Eung Seok
    Jahng, Yurngdong
    [J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 2008, 56 (04) : 607 - 609