Synthesis of 2-Aminobenzo[b]thiophenes from 4-(2-Haloaryl)-1,2,3-thiadiazoles

被引：6

作者：

Androsov, D. A. ^{[1
]}

Popova, E. A. ^{[1
]}

Petrov, M. L. ^{[1
]}

Ponyaev, A. I. ^{[1
]}

机构：

[1] Tech Univ, St Petersburg State Inst Technol, St Petersburg 190013, Russia

来源：

RUSSIAN JOURNAL OF GENERAL CHEMISTRY | 2014年 / 84卷 / 12期

关键词：

acetophenone; hydrazone; thiadiazole; thioamide; 2-aminobenzothiophene;

D O I：

10.1134/S1070363214120093

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new approach to the synthesis of 2-aminobenzo[b] thiophenes was developed on the basis of reaction of 4-aryl-1,2,3-thiadiazoles with amines in the presence of potassium carbonate. The effect of the nature of substituent in the benzene ring of the starting 4-aryl-1,2,3-thiadiazoles on the structure of the final product was studied.

引用

页码：2405 / 2408

页数：4

共 9 条

[1] DESTABILIZED CARBOCATIONS - NUCLEAR-MAGNETIC-RESONANCE DETECTION AND REACTIVITIES OF ARYL ALPHA-THIOFORMAMIDYL CATIONS [J].

ABLENAS, FJ ;

GEORGE, BE ;

MALEKI, M ;

JAIN, R ;

HOPKINSON, AC ;

LEERUFF, E .

CANADIAN JOURNAL OF CHEMISTRY, 1987, 65 (08) :1800-1803

[2] Synthesis and reactivity of 4-(2-chloro-5-nitrophenyl)-1,2,3-thiadiazole. A novel one-pot synthesis of N-substituted indole-2-thiols [J].

Androsov, Dmitry A. ;

Neckers, Douglas C. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (14) :5368-5373

[3] HALOGEN REACTIVITIES .4. KINETIC STUDY OF THE DISPLACEMENT REACTIONS OF BROMOTHIANAPHTHENES WITH PIPERIDINE [J].

BROWER, KR ;

AMSTUTZ, ED .

JOURNAL OF ORGANIC CHEMISTRY, 1954, 19 (03) :411-414

[4] ADDITION OF CYCLIC SECONDARY-AMINES TO BENZO[B]THIOPHENE AND 3-METHYLBENZO[B]THIOPHENE [J].

GRANDCLAUDON, P ;

LABLACHECOMBIER, A .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (22) :4379-4381

[5] Synthesis and pharmacology of conformationally restricted raloxifene analogues: Highly potent selective estrogen receptor modulators [J].

Grese, TA ;

Pennington, LD ;

Sluka, JP ;

Adrian, MD ;

Cole, HW ;

Fuson, TR ;

Magee, DE ;

Phillips, DL ;

Rowley, ER ;

Shetler, PK ;

Short, LL ;

Venugopalan, M ;

Yang, NN ;

Sato, M ;

Glasebrook, AL ;

Bryant, HU .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (08) :1272-1283

[6] Parallel synthesis of 1,2,3-thiadiazoles employing a "catch and release" strategy [J].

Hu, YH ;

Baudart, S ;

Porco, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) :1049-1051

[7] STUDIES ON THE WILLGERODT REACTION .4. THE PREPARATION OF NUCLEAR-SUBSTITUTED PHENYLACETIC ACIDS AND SOME FURTHER EXTENSIONS OF THE REACTION [J].

KING, JA ;

MCMILLAN, FH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1946, 68 (11) :2335-2339

[8] Synthesis and binding affinities of fluoroalkylated raloxifenes [J].

Lee, KC ;

Moon, BS ;

Lee, JH ;

Chung, KH ;

Katzenellenbogen, JA ;

Chi, DY .

BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (17) :3649-3658

[9] 2-AMINOBENZO[B]THIOPHENE . AN AROMATIC RING TAUTOMER [J].

STACY, GW ;

VILLAESC.FW ;

WOLLNER, TE .

JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (12) :4074-&

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