Characteristic features of nucleophilic substitution in the series of 4-RSO2-6-nitro-1-phenyl-1H-indazoles and benzo[d]isoxazoles

被引：6

作者：

Starosotnikov, AM ^{[1
]}

Shevelev, SA ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinskii Organ Chem Inst, Moscow 119991, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 2003年 / 52卷 / 08期

基金：

俄罗斯基础研究基金会;

关键词：

1H-indazoles; benzo[d]isoxazoles; nitro compounds; sulfones; nucleophilic substitution;

D O I：

10.1023/A:1026012922607

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Oxidation of 3-substituted 4-R-6-nitro-1-phenyl-1H-indazoles and benzo[d]isoxazoles (R = Ph, CH2CO2Me) gave the corresponding sulfones treatment of which with PhSH-K2CO3 in N-methylpyrrolidone results in replacement of only the RSO2 group in position 4 with the 6-NO2 group remaining intact, contrary to the known sequence of nucleophilic substitution for meta-arranged nucleofuges.

引用

页码：1797 / 1799

页数：3

共 5 条

[1] SERUSHKINA OV, 2002, ZH ORG KHIM, V38, P1819
[2] Regiospecific substitution of the 4-nitro group in 3-amino-4,6-dinitrobenzo[b]thiophene-2-carboxylates:: unexpected activating effect of the amino group
Shevelev, SA
Dalinger, IL
Cherkasova, TI
[J]. TETRAHEDRON LETTERS, 2001, 42 (48) : 8539 - 8541
[3] Starosotnikov A. M., 2003, IZV AKAD NAUK K, P1690
[4] Synthesis and reactions of 1-aryl-3-formyl-4,6-dinitro-1H-indazoles
Vinogradov, VM
Starosotnikov, AM
Shevelev, SA
[J]. MENDELEEV COMMUNICATIONS, 2002, (05) : 198 - 200
[5] Synthesis of 4,6-dinitro-3-R-benzo[d]isoxazoles and their transformations under the action of nucleophiles
Vinogradov, VM
Dalinger, IL
Starosotnikov, AM
Shevelev, SA
[J]. RUSSIAN CHEMICAL BULLETIN, 2001, 50 (03) : 464 - 469

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