Reaction of N-arylcarbamoyl-1,4-benzoquinone imines with sodium azide

被引:2
作者
Konovalova, S. A. [1 ]
Avdeenko, A. P. [1 ]
Sergeeva, A. G. [1 ]
Marchenko, I. L. [1 ]
机构
[1] Donbass State Engn Acad, UA-84313 Kramatorsk, Ukraine
关键词
HYDRAZOIC ACID; MONOIMINES;
D O I
10.1134/S1070428014030075
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-Arylcarbamoyl-1,4-benzoquinone imines reacted with sodium azide in completely regioselective fashion according to the 1,4-addition pattern with formation of 1-(3-azido-4-hydroxyphenyl)-3-arylureas. The reaction of N-arylcarbamoyl-2,6-dichloro-3,5-dimethyl-1,4-benzoquinone imines with sodium azide afforded N-arylcarbamoyl-2,6-diazido-3,5-dimethyl-1,4-benzoquinone imines as a result of nucleophilic substitution of the chlorine atoms.
引用
收藏
页码:346 / 350
页数:5
相关论文
共 9 条
[1]   QUINONE IMIDES .29. ADDITION OF HYDRAZOIC ACID AND PHENOLS TO PARA-QUINONEDIBENZENESULFONIMIDE AND ITS DERIVATIVES [J].
ADAMS, R ;
BLOMSTROM, DC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (14) :3405-3408
[2]  
ADAMS R, 1958, B SOC CHIM FR, P23
[3]   Reaction of N-acyl- and N-[N-arylsulfonylbenz(acet)imidoyl]-1,4-benzoquinone monoimines with hydrazoic acid [J].
Avdeenko, A. P. ;
Marchenko, I. L. .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 42 (06) :873-878
[4]   Reaction of N-alkyl(aryl)aminocarbonyl-1,4-benzoquinone monoimines with alcohols [J].
Avdeenko, A. P. ;
Konovalova, S. A. ;
Sergeeva, A. G. ;
Palamarchuk, G. V. ;
Shishkin, O. V. .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 45 (05) :674-680
[5]   Synthesis and structure of N-alkyl(aryl)aminocarbonyl-1,4-benzoquinone imines [J].
Avdeenko, A. P. ;
Konovalova, S. A. ;
Sergeeva, A. G. ;
Zubatyuk, R. I. ;
Palamarchuk, G. V. ;
Shishkin, O. V. .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 44 (12) :1765-1772
[6]  
Avdeenko A. P., 1998, RUSS J ORG CHEM+, V34, P210
[7]   Reactivity of N-arylsulfonyl-1,4-benzoquinone imines.: Reaction with hydrazoic acid [J].
Avdeenko, AP ;
Menafova, YV .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 42 (03) :403-405
[8]  
Menafova Yu.V., 1999, THESIS DNEPROPETROVS
[9]  
TOROPIN NV, 1991, ZH ORG KHIM+, V27, P376