N-Alkylation and N-amination of isomeric nitro derivatives of 3-methyl-4-(1H-pyrazol-3(5)-yl)furazan

被引：12
|
作者：
Dalinger, Igor L. [1 ]
Kormanov, Alexandr V. [1 ]
Vatsadze, Irina A. [1 ]
Shkineva, Tatyana K. [1 ]
Kozeev, Andrei M. [1 ]
Averkiev, Boris B. [2 ]
Sheremetev, Aleksei B. [1 ]
机构：
[1] Russian Acad Sci, ND Zelinskii Organ Chem Inst, Moscow 119991, Russia
[2] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia
来源：
CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2015年 / 51卷 / 09期
关键词：
furazan; nitropyrazole; N-acetonylation; N-amination; conformational analysis; multinuclear NMR; regioselectivity; X-ray structural study; NUCLEOPHILIC-SUBSTITUTION; DENSITY FUNCTIONALS; EFFICIENT SYNTHESIS; CRYSTAL-STRUCTURE; C-NUCLEOSIDE; NITROPYRAZOLES; NITROAZOLES; PYRAZOLES; FURAZANS; DESIGN;
D O I：
10.1007/s10593-015-1781-7
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction of bromoacetone and hydroxylamine-O-sulfonic acid with isomeric mono-and dinitropyrazoles containing a furazanyl moiety at position 3(5) gave pairs of regioisomeric products from pyrazole ring N-acetonylation and N-amination, respectively, that were characterized in detail by multinuclear NMR spectroscopy. X-ray structural study of the four synthesized N-amino derivatives indicated a non-planar structure, while the conformational analysis pointed to conformational lability of such molecules, and the role of intermolecular interactions in determining the crystal structure.
引用
收藏
页码：819 / 828
页数：10
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