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 40 条

[1] The different, but interesting behaviors of benzyl systems in the Willgerodt-Kindler reaction under solvent-free conditions
Aghapoor, K
Darabi, HR
Tabar-Heydar, K
[J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2002, 177 (05) : 1183 - 1187
[2] Synthesis of 1,1-Dialkylindolium-2-thiolates via Base-Induced Transformation of 4-(2-Chloro-5-nitrophenyl)-1,2,3-thiadiazole in the Presence of Secondary Amines
Androsov, Dmitry A.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (21) : 8612 - 8614
[3] Synthesis and reactivity of 4-(2-chloro-5-nitrophenyl)-1,2,3-thiadiazole. A novel one-pot synthesis of N-substituted indole-2-thiols
Androsov, Dmitry A.
Neckers, Douglas C.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (14) : 5368 - 5373
[4] NEW ACCESS TO 2-(ARYLAZO)INDOLES, 2-(ARYLHYDRAZO)INDOLES, AND 2-AMINOINDOLES, 2-AMINOBENZOFURANS, AND 2-AMINOTHIANAPHTHENES
BENINCORI, T
SANNICOLO, F
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (06) : 1309 - 1312
[5] NITROBENZO[B]THIOPHENES
BOSWELL, DE
BRENNAN, JA
LANDIS, PS
RODEWALD, PG
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1968, 5 (01) : 69 - +
[6] Synthesis of [1]benzothieno[3,2-d]pyrimidines substituted with electron donating substituents on the benzene ring
Bridges, AJ
Zhou, HR
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1997, 34 (04) : 1163 - 1172
[7] HALOGEN REACTIVITIES .4. KINETIC STUDY OF THE DISPLACEMENT REACTIONS OF BROMOTHIANAPHTHENES WITH PIPERIDINE
BROWER, KR
AMSTUTZ, ED
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1954, 19 (03) : 411 - 414
[8] KINETICS AND MECHANISM OF THE REACTION OF THIONYL CHLORIDE WITH SUBSTITUTED ACETOPHENONE SEMICARBAZONES - THE SYNTHESIS OF 1,2,3-THIADIAZOLES
BUTLER, RN
ODONOGHUE, DA
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (05): : 1223 - 1227
[9] PROTON MAGNETIC RESONANCE SPECTRA OF SOME BENZO[B]THIOPHENS . AN INVESTIGATION OF SUBSTITUENT EFFECTS IN A HETEROAROMATIC SYSTEM
CADDY, B
MARTINSM.M
NORRIS, RK
REID, ST
STERNHEL.S
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1968, 21 (07) : 1853 - &
[10] 1,2-BENZISOTHIAZOLES .2. REACTIONS OF 3-CHLORO-1,2-BENZISOTHIAZOLE WITH CARBANIONS
CARRINGTON, DE
CLARKE, K
SCROWSTON, RM
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (23): : 3903 - +

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