Synthesis and Tautomerism of Substituted Pyrazolo[4,3-c]pyrazoles
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14740%2F13%3A00066252" target="_blank" >RIV/00216224:14740/13:00066252 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1002/ejoc.201300606" target="_blank" >http://dx.doi.org/10.1002/ejoc.201300606</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/ejoc.201300606" target="_blank" >10.1002/ejoc.201300606</a>
Alternative languages
Result language
angličtina
Original language name
Synthesis and Tautomerism of Substituted Pyrazolo[4,3-c]pyrazoles
Original language description
Fused five-membered nitrogen heterocycles comprise a very important group of compounds frequently utilized in pharmaceutical applications. In this study, we report the first systematic synthesis of substituted pyrazolo[4,3-c]pyrazoles and three regio-isomers of their N-methyl derivatives. All compounds were fully characterized by using NMR spectroscopy in solution and selected compounds also by X-ray diffraction in the solid state. 1H, 13C, and 15N NMR data for all isomers were interpreted by DFT calculations of nuclear shielding constants and indirect spin-spin coupling constants. The N-methyl isomers were used in the following steps as model compounds to investigate a potential N1-H/N4-H, N2-H/N4-H, and N1-H/N5-H tautomerism of 3,6-substituted pyrazolo[4,3-c]pyrazoles by using low-temperature NMR spectroscopy. All bases were shown to occur predominantly in the N1-H/N4-H tautomeric form and the structure of minor form was governed by the substituents at positions 3 and 6.
Czech name
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2013
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
European Journal of Organic Chemistry
ISSN
1434-193X
e-ISSN
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Volume of the periodical
2013
Issue of the periodical within the volume
30
Country of publishing house
DE - GERMANY
Number of pages
12
Pages from-to
6811-6822
UT code for WoS article
000328739500009
EID of the result in the Scopus database
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