A practical synthetic route to benzofuro[2,3-b]pyridine and trifluoromethyl-α-carbolines

被引：21

作者：

Iaroshenko, Viktor O. ^{[1
,2
]}

Groth, Ulrich ^{[1
]}

Kryvokhyzha, Nadiya V. ^{[3
]}

Obeid, Samra ^{[1
]}

Tolmachev, Andrei A. ^{[2
,4
]}

Wesch, Thomas ^{[1
]}

机构：

[1] Univ Konstanz, Fachbereich Chem, D-78457 Constance, Germany

[2] Natl Taras Shevchenko Univ, UA-01033 Kiev, Ukraine

[3] Univ Glasgow, Dept Chem, Glasgow G12 8QQ, Lanark, Scotland

[4] Enamine Ltd, UA-01103 Kiev, Ukraine

来源：

SYNLETT | 2008年 / 03期

关键词：

furanamine; indoleamine; pyridine; annulation; electrophilic aromatic substitution;

D O I：

10.1055/s-2008-1032042

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In situ generated benzofuran-2-amine reacts with 1,3-CCC-diclectrophiles, such as CF3-containing beta-diketones, 3-formylchromone, methyl-2,4-dioxopentanoate and pentafluorobenzaldehyde, and the reaction leads to the formation of benzofuro[2,3-b]pyridine ring system. By using a similar approach 4-trifluoromethyl-alpha-carbolines were synthesized starting from indole-2-amine.

引用

页码：343 / 346

页数：4

共 50 条

[31] Synthesis of benzofuro[2,3-b]benzofuran derivatives under Hoesch reaction conditions
Kawecki, R
Mazurek, AP
Kozerski, L
Maurin, JK
SYNTHESIS-STUTTGART, 1999, (05): : 751 - 753
[32] Identification of benzofuro[2,3-b]quinoline derivatives as a new class of antituberculosis agents
Yang, Chiao-Li
Tseng, Chih-Hua
Chen, Yeh-Long
Lu, Chih-Ming
Kao, Chai-Lin
Wu, Ming-Hsien
Tzeng, Cherng-Chyi
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (02) : 602 - 607
[33] Multicomponent design of chromeno[2,3-b]pyridine systems
Elinson, Michail N.
Ryzhkova, Yuliya E.
Ryzhkov, Fedor, V
RUSSIAN CHEMICAL REVIEWS, 2021, 90 (01) : 94 - 115
[34] Synthesis of 4-Arylthieno[2,3-b]pyridines and 4-Aminothieno[2,3-b]pyridines via a Regioselective Bromination of Thieno[2,3-b]pyridine
Lucas, Simon C. C.
Moore, Jane E.
Donald, Craig S.
Hawkins, Janet L.
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (24): : 12594 - 12598
[35] Preparation of Novel Pyrrolo[2,3-b] pyridine Derivatives via a New Concise Synthetic Approach
Guo, Na
Jia, Haiyong
You, Xing
Jiang, Du
Lu, Kui
Yu, Peng
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2015, 36 (04) : 1143 - 1147
[36] STEREOCONTROLLED OXIDATIVE ADDITIONS UPON 1,4-DIHYDROPYRIDINES: SYNTHESIS OF HEXAHYDROFURO[2,3-b]PYRIDINE AND HEXAHYDROPYRANO[2,3-b]PYRIDINE DERIVATIVES
Kumar, Rakesh
Kumar, Dhiraj
Prasad, Ashok K.
SYNTHETIC COMMUNICATIONS, 2013, 43 (04) : 520 - 536
[37] New route to furo[2,3-b]quinoline derivatives
Traven, VF
Podkhalyuzina, NY
Kanevskii, DS
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2002, (03): : 395 - 396
[38] Synthesis and reactivity of thieno[2,3-b]pyridine-2,3-diamines
Lipunov, M. M.
Kaigorodova, E. A.
Konyushkin, L. D.
Firgang, S. I.
Krapivin, G. D.
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2007, (09): : 1400 - 1408
[39] Synthesis and reactivity of thieno[2,3-b]pyridine-2,3-diamines
Lipunov M.M.
Kaigorodova E.A.
Konyushkin L.D.
Firgang S.I.
Krapivin G.D.
Chemistry of Heterocyclic Compounds, 2007, 43 (09) : 1189 - 1196
[40] REACTIVITY OF THIENO[2,3-B]PYRIDINE TOWARDS ELECTROPHILIC SUBSTITUTION
ALUNNI, S
CLEMENTI, S
KLEMM, LH
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1976, (10): : 1135 - 1139

← 1 2 3 4 5 →