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

页码：819 / 828

页数：10

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