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 [J].
Abe, Takumi ;
Ikeda, Toshiaki ;
Yanada, Reiko ;
Ishikura, Minoru .
ORGANIC LETTERS, 2011, 13 (13) :3356-3359
[2]   Synthesis of 4,7-indoloquinones from indole-7-carbaldehydes by Dakin oxidation [J].
Alamgir, Mahiuddin ;
Mitchell, Peter S. R. ;
Bowyer, Paul K. ;
Kumar, Naresh ;
Black, David StC. .
TETRAHEDRON, 2008, 64 (30-31) :7136-7142
[3]   Electrosynthesis of tryptanthrin [J].
Batanero, Belen ;
Barba, Fructuoso .
TETRAHEDRON LETTERS, 2006, 47 (47) :8201-8203
[4]   THE IDENTITY OF CANDIDINE AND QINGDAINONE [J].
BERGMAN, J .
PHYTOCHEMISTRY, 1989, 28 (12) :3547-3547
[5]   STRUCTURE DETERMINATION OF CANDIDINE, A VIOLET INDOLIC CONSTITUENT FROM CULTURE SOLUTIONS OF CANDIDA-LIPOLYTICA [J].
BERGMAN, J ;
TILSTAM, U .
TETRAHEDRON, 1985, 41 (14) :2883-2884
[6]   I2/TBHP-Catalyzed Chemoselective Amination of Indoles [J].
Cai, Zhong-Jian ;
Wang, Shun-Yi ;
Ji, Shun-Jun .
ORGANIC LETTERS, 2013, 15 (20) :5226-5229
[7]   Alkaloids from the Root of Isatis indigotica [J].
Chen, Minghua ;
Gan, Lishe ;
Lin, Sheng ;
Wang, Xiaoliang ;
Li, Li ;
Li, Yuhuan ;
Zhu, Chenggen ;
Wang, Yanan ;
Jiang, Bingya ;
Jiang, Jiandong ;
Yang, Yongchun ;
Shi, Jiangong .
JOURNAL OF NATURAL PRODUCTS, 2012, 75 (06) :1167-1176
[8]   Total Synthesis of a Pyrroloindoloquinazoline Alkaloid [J].
Gahtory, Digvijay ;
Chouhan, Mangilal ;
Sharma, Ratnesh ;
Nair, Vipin A. .
ORGANIC LETTERS, 2013, 15 (15) :3942-3945
[9]   Design, Synthesis, and Structure-Activity Relationship Studies of Tryptanthrins As Antitubercular Agents [J].
Hwang, Jae-Min ;
Oh, Taegwon ;
Kaneko, Takushi ;
Upton, Anna M. ;
Franzblau, Scott G. ;
Ma, Zhenkun ;
Cho, Sang-Nae ;
Kim, Pilho .
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 [J].
Jahng, Katherine Chae ;
Kim, Seung Ill ;
Kim, Dong Hyeon ;
Seo, Chang Seob ;
Son, Jong-Keun ;
Lee, Seung Ho ;
Lee, Eung Seok ;
Jahng, Yurngdong .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2008, 56 (04) :607-609