Reaction of 3-Iodoindole with 1,4-Naphthoquinones

被引:4
作者
Tanoue, Yasuhiro [1 ]
Teraoka, Takashi [1 ]
Kai, Norihisa [1 ]
Nagai, Takeshi [2 ]
Ushio, Kazutoshi [3 ]
机构
[1] Univ Shimonoseki, Dept Food Sci & Technol, Shimonoseki, Yamaguchi 7596595, Japan
[2] Tokyo Univ Agr, Dept Food Sci & Technol, Abashiri, Hokkaido 0992493, Japan
[3] Niihama Natl Coll Technol, Dept Appl Chem & Biotechnol, Yakumocho, Niihama 7928580, Japan
关键词
FACILE SYNTHESIS; INDOLE;
D O I
10.1002/jhet.492
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The usefulness of 3-iodoindole available for introduction of an indole unit is presented. The reaction of 3-iodoindole with 2-bromo(or methyl)-1,4-naphthoquinone in acetic acid gave 2-bromo(or methyl)-3-(3-indolyl)-1,4-naphthoquinone. On the other hand, the reaction of 3-iodoindole with 2-bromo-1,4-naphthoquinone in the presence of cesium carbonate in acetonitrile produced 2-(1-indolyl-3-iodo)-1,4-naphthoquinone.
引用
收藏
页码:1447 / 1449
页数:3
相关论文
共 8 条
[1]   INDOXYL ACETATE FROM INDOLE [J].
ARNOLD, RD ;
NUTTER, WM ;
STEPP, WL .
JOURNAL OF ORGANIC CHEMISTRY, 1959, 24 (01) :117-118
[2]   MELANIN AND ITS PRECURSORS .2. MODEL EXPERIMENTS ON THE REACTIONS BETWEEN QUINONES AND INDOLES, AND CONSIDERATION OF A POSSIBLE STRUCTURE FOR THE MELANIN POLYMER [J].
BULOCK, JD ;
HARLEYMASON, J .
JOURNAL OF THE CHEMICAL SOCIETY, 1951, (MAR) :703-712
[3]  
CORRADINI MG, 1989, GAZZ CHIM ITAL, V119, P153
[4]   ROYAL PURPLE-DYE - THE CHEMICAL RECONSTRUCTION OF THE ANCIENT MEDITERRANEAN INDUSTRY [J].
MCGOVERN, PE ;
MICHEL, RH .
ACCOUNTS OF CHEMICAL RESEARCH, 1990, 23 (05) :152-158
[5]   Synthesis of 2-(3-indolyl)-1,4-naphthoquinones using 3-iodoindoles [J].
Tanoue, Y ;
Hamada, M ;
Kai, N ;
Sakata, K ;
Hashimoto, M ;
Nagai, T .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2005, 42 (06) :1195-1199
[6]   A facile synthesis of 6,6′- and 5,5′-dihalogenoindigos [J].
Tanoue, Y ;
Sakata, K ;
Hashimoto, M ;
Hamada, M ;
Kai, N ;
Nagai, T .
DYES AND PIGMENTS, 2004, 62 (02) :101-105
[7]   A facile synthesis of Tyrian purple based on a biosynthetic pathway [J].
Tanoue, Y ;
Terada, A ;
Sakata, K ;
Hashimoto, M ;
Morishita, SI ;
Hamada, M ;
Kai, N ;
Nagai, T .
FISHERIES SCIENCE, 2001, 67 (04) :726-729
[8]   Recent progress in the chemistry of non-monoterpenoid indole alkaloids [J].
Toyota, M ;
Ihara, N .
NATURAL PRODUCT REPORTS, 1998, 15 (04) :327-340