A convenient approach towards 2-and 3-aminobenzo[b]thiophenes

被引：24

作者：

Androsov, Dmitry A. ^{[1
,2
]}

Solovyev, Andrey Y. ^{[2
]}

Petrov, Mikhail L. ^{[1
]}

Butcher, Ray J. ^{[3
]}

Jasinski, Jerry P. ^{[4
]}

机构：

[1] Str Petersburg State Inst Technol, Dept Organ Chem, St Petersburg 190013, Russia

[2] Bowling Green State Univ, Ctr Photochem Sci, Bowling Green, OH 43403 USA

[3] Howard Univ, Dept Chem, Washington, DC 20059 USA

[4] Keene State Coll, Dept Chem, Keene, NH 03435 USA

来源：

TETRAHEDRON | 2010年 / 66卷 / 13期

关键词：

PALLADIUM-CATALYZED AMINATION; WILLGERODT-KINDLER REACTION; ESTROGEN-RECEPTOR MODULATORS; ONE-POT SYNTHESIS; SECONDARY-AMINES; 1,2,3-THIADIAZOLES; EFFICIENT; DERIVATIVES; MECHANISM; BASE;

D O I：

10.1016/j.tet.2010.01.069

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of 1-(2-chloro-5-nitrophenyl)ethanone via Willgerodt-Kindler route with primary or secondary amines and Sulfur allows a simple, efficient one-pot synthesis of 3-aminobenzo[b]thiophenes. Base-catalyzed transformation of 4-(2-chloro-5-nitrophenyl)-1,2,3-thiadiazole in the presence of primary and secondary amines offers a convenient approach towards 2-aminobenzo[b]thiophenes. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：2474 / 2485

页数：12

共 50 条

[41] Convenient synthesis of 3-substituted benzo[b]thiophenes by iodine-mediated cyclization of α-substituted 2-(1-Phenylethylthio)styrenes
Kobayashi, Kazuhiro
Nakamura, Daizo
Miyamoto, Kazuna
Morikawa, Osamu
Konishi, Hisatoshi
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2007, 80 (09) : 1780 - 1784
[42] SYNTHESIS AND TAUTOMERIC PROPERTIES OF SOME POTENTIAL 2-HYDROXYTHIENO[3,2-B]THIOPHENES AND 2-HYDROXYTHIENO[2,3-B]THIOPHENES
MARTELLI, G
TESTAFERRI, L
TIECCO, M
ZANIRATO, P
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (23): : 3384 - 3391
[43] Controlled Synthesis of 2-and 3-Substituted Benzo[b]furans
Pei, Tao
Chen, Cheng-yi
DiMichele, Lisa
Davies, Ian W.
ORGANIC LETTERS, 2010, 12 (21) : 4972 - 4975
[44] Regiospecific Synthesis of 2-Halo-3-(2′-glucalyl)benzo[b]thiophenes
Kinfe, Henok H.
Makolo, Felix L.
Adokoh, Christian K.
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (16): : 7718 - 7722
[45] ORGN 126-Preparation of 5-nitro-2-aminobenzo[b]thiophenes and 1-(2-amino-5-nitrophenyl) ethanones via microwave irradiation
Rais, Afsha A.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 237
[46] An approach to the construction of 3-aryl- and 3-hydroxy-substituted benzo[b]selenopheno[2,3-d]thiophenes
Irgashev, Roman A.
Rusinov, Gennady L.
TETRAHEDRON LETTERS, 2022, 110
[47] DYEING PROPERTIES OF REACTIVE AZO DISPERSE DYES FROM N-ETHYL-N-BETA-VINYLSULPHONYLETHYL-META-TOLUIDINE AS COUPLING COMPONENT AND SUBSTITUTED 3-AMINOBENZO (B) THIOPHENS AS DIAZO COMPONENTS
NISHIDA, K
ANDO, Y
SHIMAZU, K
KASHIMA, T
MORIMOTO, T
IWAMOTO, H
KANAMORI, T
JOURNAL OF THE SOCIETY OF DYERS AND COLOURISTS, 1981, 97 (11): : 469 - 470
[48] 2-AMINOBENZO[B]THIOPHENECARBOXYLIC ESTERS FROM 3-HYDROXY-2-NITRO-1-THIOCHROMONE
EIDEN, F
FELBERMEIR, G
ARCHIV DER PHARMAZIE, 1984, 317 (08) : 675 - 680
[49] A convenient approach towards 2′-analogs of zoapatanol from D-glucose
Ovaa, H
van der Marel, GA
van Boom, JH
TETRAHEDRON LETTERS, 2001, 42 (33) : 5749 - 5752
[50] RESEARCH IN SERIES OF BENZO(B)THIOPHENES .1. 3 OR 2-(4-DIALKYLAMINOALKYLOXY-3,5-HALOGENO-2-BENZOYL) BENZO(B)THIOPHENES
CLAEYS, N
GOLDENBE.C
WANDESTR.R
DERAY, E
DESCAMPS, M
DELAUNOI.G
BAUTHIER, J
CHARLIER, R
CHIMICA THERAPEUTICA, 1972, 7 (05): : 377 - 384

← 1 2 3 4 5 →