About: Synthesis and Tautomerism of Substituted Pyrazolo[4,3-c]pyrazoles

Facets (new session)
Description
Metadata
Settings
- owl:sameAs
- Inference Rule:

About: Synthesis and Tautomerism of Substituted Pyrazolo[4,3-c]pyrazoles Goto Sponge NotDistinct Permalink

An Entity of Type : http://linked.opendata.cz/ontology/domain/vavai/Vysledek, within Data Space : linked.opendata.cz associated with source document(s)

Attributes	Values
rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
rdfs:seeAlso	http://dx.doi.org/10.1002/ejoc.201300606
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. 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. (en)
Title	Synthesis and Tautomerism of Substituted Pyrazolo[4,3-c]pyrazoles Synthesis and Tautomerism of Substituted Pyrazolo[4,3-c]pyrazoles (en)
skos:prefLabel	Synthesis and Tautomerism of Substituted Pyrazolo[4,3-c]pyrazoles Synthesis and Tautomerism of Substituted Pyrazolo[4,3-c]pyrazoles (en)
skos:notation	RIV/00216224:14740/13:00066252!RIV14-MSM-14740___
http://linked.open...avai/predkladatel	Středoevropský technologický institut
http://linked.open...avai/riv/aktivita	P
http://linked.open...avai/riv/aktivity	P(ED1.1.00/02.0068), P(GAP206/12/0539)
http://linked.open...iv/cisloPeriodika	30
http://linked.open...vai/riv/dodaniDat	2014
http://linked.open...aciTvurceVysledku	Toušek, Jaromír Maier, Lukáš Nečas, Marek Marek, Radek Kadam, Shivaji Sambhaji
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Masarykova univerzita / Středoevropský technologický institut
http://linked.open...dnocenehoVysledku	109495
http://linked.open...ai/riv/idVysledku	RIV/00216224:14740/13:00066252
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	NMR chemical shift; synthesis of pyrazolo[4.3-c]pyrazoles; stability of tautomers; regioisomers; low-temperature NMR; X-ray diffraction; DFT calculations (en)
http://linked.open.../riv/klicoveSlovo	NMR chemical shift low-temperature NMR regioisomers stability of tautomers synthesis of pyrazolo[4.3-c]pyrazoles X-ray diffraction DFT calculations
http://linked.open...odStatuVydavatele	DE - Spolková republika Německo
http://linked.open...ontrolniKodProRIV	[72FE4C30AE19]
http://linked.open...i/riv/nazevZdroje	European Journal of Organic Chemistry
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	5 (xsd:int)
http://linked.open...cetTvurcuVysledku	8 (xsd:int)
http://linked.open...vavai/riv/projekt	Central european institute of technology Structure and dynamics of transition-metal complexes and their interaction with cavitands
http://linked.open...UplatneniVysledku	2013
http://linked.open...v/svazekPeriodika	2013
http://linked.open...iv/tvurceVysledku	Marek, Radek Nečas, Marek Kadam, Shivaji Sambhaji Maier, Lukáš Toušek, Jaromír Kostakis, Ioannis Marakos, Panagiotis Pouli, Nicole
http://linked.open...ain/vavai/riv/wos	000328739500009
issn	1434-193X
number of pages	12 (xsd:int)
http://bibframe.org/vocab/doi	10.1002/ejoc.201300606
http://localhost/t...ganizacniJednotka	14740

Faceted Search & Find service v1.16.118 as of Jun 21 2024

Alternative Linked Data Documents: ODE Content Formats:

RDF

ODATA

Microdata

About

OpenLink Virtuoso version 07.20.3240 as of Jun 21 2024, on Linux (x86_64-pc-linux-gnu), Single-Server Edition (126 GB total memory, 48 GB memory in use)
Data on this page belongs to its respective rights holders.
Virtuoso Faceted Browser Copyright © 2009-2024 OpenLink Software