Synthesis of 4-Acetoxyindoles and Related Derivatives by Means of Air Oxidation of 4-Oxo-4,5,6,7-tetrahydroindoles Obtained from Nitroalkenes and Cyclohexane-1,3-diones

被引:24
作者
Arai, Masaki [1 ]
Miyauchi, Yayoi [2 ]
Miyahara, Tadashi [2 ]
Ishikawa, Teruhiko [1 ,2 ]
Saito, Seiki [1 ]
机构
[1] Okayama Univ, Grad Sch Nat Sci & Technol, Dept Med & Bioengn Sci, Okayama 7008530, Japan
[2] Okayama Univ, Grad Sch Educ, Okayama 7008530, Japan
关键词
indoles; cyclohexane-1,3-diones; nitroalkenes; Michael additions; oxidations; SUBSTITUENTS; DISCOVERY; VERSATILE; PSILOCIN; INDOLES;
D O I
10.1055/s-0028-1087386
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel method for synthesizing 4-hydroxyindole derivatives from cyclohexane-1,3-diones and nitroalkenes have been developed in which a newly developed air oxidation of 4-oxo-4,5,6,7-tetrahydroindoles is playing a crucial role.
引用
收藏
页码:122 / 126
页数:5
相关论文
共 21 条
[1]   SYNTHESES OF INDOLES AND CARBOLINES VIA AMINOACETALDEHYDE ACETALS [J].
BOBBITT, JM ;
KULKARNI, CL ;
DUTTA, CP ;
KOFOD, H ;
CHIONG, KN .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (18) :3541-3544
[2]   Preparation of the 4-hydroxytryptamine scaffold via palladium-catalyzed cyclization: A practical and versatile synthesis of psilocin [J].
Gathergood, N ;
Scammells, PJ .
ORGANIC LETTERS, 2003, 5 (06) :921-923
[3]   PALLADIUM(0)-CATALYZED SYNTHESES OF INDOLOQUINONES [J].
HEGEDUS, LS ;
MULHERN, TA ;
MORI, A .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (22) :4282-4288
[4]   One-pot multistep synthesis of 4-acetoxy-2-amino-3-arylbenzofurans from 1-aryl-2-nitroethylenes and cyclohexane-1,3-diones [J].
Ishikawa, T ;
Miyahara, T ;
Asakura, M ;
Higuchi, S ;
Miyauchi, Y ;
Saito, S .
ORGANIC LETTERS, 2005, 7 (07) :1211-1214
[5]   Revisiting [3+3] route to 1,3-cyclohexanedione frameworks: Hidden aspect of thermodynamically controlled enolates [J].
Ishikawa, T ;
Kadoya, R ;
Arai, M ;
Takahashi, H ;
Kaisi, Y ;
Mizuta, T ;
Yoshikai, K ;
Saito, S .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (24) :8000-8009
[6]   Air oxidation of 2-aryl-1-tetralones in basic, neutral, and acidic media: An unprecedented oxidative aryl migration to 2-aryloxy-1-naphthols under acidic condition [J].
Ishikawa, T ;
Hino, K ;
Yoneda, T ;
Murota, M ;
Yamaguchi, K ;
Watanabe, T .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (15) :5691-5695
[7]   Synthesis of 1,2,3,4-tetrasubstituted pyrrole derivatives via the palladium-catalyzed reaction of 1,3-diketones with methyleneaziridines [J].
Kathriarachchi, Kalum K. A. D. S. ;
Siriwardana, Amal I. ;
Nakamura, Itaru ;
Yamamoto, Yoshinori .
TETRAHEDRON LETTERS, 2007, 48 (13) :2267-2270
[8]   Direct and practical synthesis of 2-arylbenzoxazoles promoted by activated carbon [J].
Kawashita, Y ;
Nakamichi, N ;
Kawabata, H ;
Hayashi, M .
ORGANIC LETTERS, 2003, 5 (20) :3713-3715
[9]  
LEONARDA P, 2008, TETRAHEDRON LETT, V49, P459
[10]   Discovery of 4-amino and 4-hydroxy-1-aroylindoles as potent tubulin polymerization inhibitors [J].
Liou, Jing-Ping ;
Wu, Zi-Yi ;
Kuo, Ching-Chuan ;
Chang, Chi-Yen ;
Lu, Pei-Yi ;
Chen, Chi-Ming ;
Hsieh, Hsing-Pang ;
Chang, Jang-Yang .
JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (14) :4351-4355