Selective reduction of the nitro group in the presence of the azoxy group.: Synthesis of 2-(alkyl-NNO-azoxy)anilines

被引：6

作者：

Lipilin, DL ^{[1
]}

Churakov, AM ^{[1
]}

Strelenko, YA ^{[1
]}

Tartakovsky, VA ^{[1
]}

机构：

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

来源：

RUSSIAN CHEMICAL BULLETIN | 2002年 / 51卷 / 02期

关键词：

nitrosobenzenes; nitrobenzenes; anilines; azoxy compounds; reduction of the nitro group;

D O I：

10.1023/A:1015463912286

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Tin(II) chloride selectively reduces the aromatic nitro group to the amino group, the azoxy group remaining intact. This allows the preparation of 2-(R-NNO-azoxy)anilines from 2-(R-NNO-azoxy)nitrobenzenes bearing electron-donating or weak electron-withdrawing substituents (Me or Br) in the benzene ring and alkyl substituents at the distal N atom of the azoxy group. The presence of electron-withdrawing substituents at the azoxy group (for example, CO2Et) leads to a change in the direction of the reaction resulting in selective reduction of the azoxy group to the hydrazo group.

引用

页码：311 / 318

页数：8

共 50 条

[1] Selective reduction of the nitro group in the presence of the azoxy group. Synthesis of 2-(alkyl-NNO-azoxy)anilines
D. L. Lipilin
A. M. Churakov
Yu. A. Strelenko
V. A. Tartakovsky
Russian Chemical Bulletin, 2002, 51 : 311 - 318
[2] Selective Reduction of an Aromatic Nitro Group to an Azoxy Unit in the Presence of an Aliphatic Nitro Group
Ulrich Siemeling
Thomas Türk
Udo Vorfeld
Heinrich Fink
Monatshefte für Chemie / Chemical Monthly, 2003, 134 : 419 - 423
[3] Selective reduction of an aromatic nitro group to an azoxy unit in the presence of an aliphatic nitro group
Siemeling, U
Türk, T
Vorfeld, U
Fink, H
MONATSHEFTE FUR CHEMIE, 2003, 134 (03): : 419 - 423
[4] SYNTHESIS OF BROMINATED 2-(TERT-BUTYL-NNO-AZOXY)ANILINES
CHURAKOV, AM
SMIRNOV, OY
IOFFE, SL
STRELENKO, YA
TARTAKOVSKY, VA
RUSSIAN CHEMICAL BULLETIN, 1994, 43 (09) : 1532 - 1535
[5] Novel energetic aminofurazans with a nitro-NNO-azoxy group
Leonov, Nikita E.
Semenov, Sergei E.
Klenov, Michael S.
Churakova, Aleksandr M.
Strelenko, Yurii A.
Pivkina, Alla N.
V. Fedyanin, Ivan
Lempert, David B.
Kon'kova, Tatiana S.
Matyushin, Yurii N.
Miroshnichenko, Evgeny A.
Tartakovsky, Vladimir A.
MENDELEEV COMMUNICATIONS, 2021, 31 (06) : 789 - 791
[6] A NEW REACTION OF THE AZOXY GROUP WITH ALKYL THIOLATES - REDUCTION TO AMINO VIA A SULFENAMIDO INTERMEDIATE
DARIO, MT
MONTANARI, S
PARADISI, C
SCORRANO, G
TETRAHEDRON LETTERS, 1994, 35 (02) : 301 - 302
[7] SELECTIVE REDUCTION OF A BENZYLOXYAMINO GROUP IN THE PRESENCE OF A NITRO GROUP
TAYLOR, EC
BARTON, JW
JOURNAL OF ORGANIC CHEMISTRY, 1959, 24 (01): : 127 - 128
[8] Ammonium Dinitramide as a Prospective N-NO2 Synthon: Electrochemical Synthesis of Nitro-NNO-Azoxy Compounds from Nitrosoarenes
Budnikov, Alexander S.
Leonov, Nikita E.
Klenov, Michael S.
Shevchenko, Mikhail I.
Dvinyaninova, Tatiana Y.
Krylov, Igor B.
Churakov, Aleksandr M.
Fedyanin, Ivan V.
Tartakovsky, Vladimir A.
Terent'ev, Alexander O.
MOLECULES, 2024, 29 (23):
[9] Synthesis of energetic compounds bearing a (3,4-dinitro-1H-pyrazol-1-yl)-NNO-azoxy group
Konnov, A. A.
Dubrovin, I. M.
Klenov, M. S.
Anikin, O. V.
Churakov, A. M.
Strelenko, Yu. A.
Pivkina, A. N.
Tartakovsky, V. A.
RUSSIAN CHEMICAL BULLETIN, 2021, 70 (11) : 2189 - 2194
[10] UNSOLVATED MAGNESIUM DIISOPROPYLAMIDE IN ORGANIC-SYNTHESIS .2. REDUCTION OF NITRO, NITROSO, AND AZOXY COMPOUNDS
SANCHEZ, R
VEST, G
SCOTT, W
ENGEL, PS
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (17): : 4026 - 4027

← 1 2 3 4 5 →