Chlorination of 2-substituted 1-hydroxyindoles

被引：2

作者：

Chirkova, Zh. V. ^{[1
]}

Kabanova, M. V. ^{[1
]}

Filimonov, S. I. ^{[1
]}

Samet, A. V. ^{[2
]}

Stashina, G. A. ^{[2
]}

Sudzilovskaya, T. N. ^{[1
]}

机构：

[1] Yaroslavl State Tech Univ, 88 Moskovskii Prosp, Yaroslavl 150023, Russia

[2] Russian Acad Sci, ND Zelinsky Inst Organ Chem, 47 Leninsky Prosp, Moscow 119991, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 2018年 / 67卷 / 06期

关键词：

chlorination; N-chlorosuccinimide; 1-hydroxyindole-5,6-dicarbonitriles; 1-hydroxypyrrolo[3,4-f]indole-5,7(1H,6H)-diones; 3,3-dichloro-3H-indole 1-oxides; 3-chloro-1-hydroxyindole-5,6-dicarbonitriles; 3-chloroindole-5,6-dicarbonitriles; reduction; TERTIARY AMINE OXIDES; EFFICIENT SYNTHESIS; MONOAMINE-OXIDASE; IN-SITU; DERIVATIVES; HALOGENATION; ACID; OXIDATION; ESTER;

D O I：

10.1007/s11172-018-2184-6

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chlorination of 1-hydroxyindole-5,6-dicarbonitriles and 1-hydroxypyrrolo[3,4-f]indole-5,7(1H,6H)-diones with N-chlorosuccinimide afforded previously unknown 3,3-dichloro-3Hindole 1-oxides instead of the expected 3-chloro-1-hydroxyindoles. The latter, however, were prepared in good yields by treatment of the above 3,3-dichloro-3H-indole 1-oxides with piperidine in ethanol. Reduction of 3,3-dichloro-5,6-dicyano-3H-indole 1-oxides with Zn in AcOH yielded the corresponding 3-chloroindole-5,6-dicarbonitriles.

引用

页码：1083 / 1087

页数：5

共 28 条

[21]

NAGAYOSHI T, 1984, CHEM PHARM BULL, V32, P3678

[22]

NAGAYOSHI T, 1981, CHEM PHARM BULL, V29, P1920

[23] Selective Halogenation Using an Aniline Catalyst [J].

Samanta, Ramesh C. ;

Yamamoto, Hisashi .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (34) :11976-11979

[24] Heterocyclic analogs of 5,12-naphthacenequinone 7. Synthesis of naphtho-[2,3-f]isatin-5,10-dione derivatives [J].

Shchekotikhin, A. E. ;

Luzikov, Y. N. ;

Sinkevich, Y. B. ;

Buyanov, V. N. ;

Preobrazhenskaya, M. N. .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2008, 44 (10) :1245-1249

[25] Efficient synthesis of 3-selanyl- and 3-sulfanylindoles employing trichloroisocyanuric acid and dichalcogenides [J].

Silveira, Claudio C. ;

Mendes, Samuel R. ;

Wolf, Lucas ;

Martins, Guilherme M. ;

von Muehlen, Lisandro .

TETRAHEDRON, 2012, 68 (51) :10464-10469

[26] Oxygenation of 2,3-dihydroindoles [J].

Slätt, J ;

Bergman, J .

TETRAHEDRON, 2002, 58 (45) :9187-9191

[27]

VANDERWOLF L, 1977, RECL TRAV CHIM PAY B, V96, P72

[28] Simple and efficient procedures for selective preparation of 3-haloindoles and 2,3-dihaloindoles by using 1,3-dibromo-5, 5-dimethylhydantoin and 1,3-dichloro-5,5-dimethylhydantoin [J].

Yan, Jianwei ;

Ni, Tianjun ;

Yan, Fulin .

TETRAHEDRON LETTERS, 2015, 56 (09) :1096-1098

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