Reactions of 1,2-diaza-1,3-butadienes with propargyl alcohol as an approach to novel bi-heterocyclic systems

2016 ◽  
Vol 14 (37) ◽  
pp. 8674-8678 ◽  
Author(s):  
L. De Crescentini ◽  
F. R. Perrulli ◽  
G. Favi ◽  
S. Santeusanio ◽  
G. Giorgi ◽  
...  
Keyword(s):  
Click Reaction ◽  
Propargyl Alcohol ◽  
Wittig Rearrangement ◽  
Triazole Derivatives

Starting from easily available 1,2-diaza-1,3-dienes and propargyl alcohol, spyro-bicyclic systems, through 2,3-Wittig rearrangement, and pyrazolone–triazole derivatives, through a typical “click reaction”, are obtained.

scholarly journals Fabrication of copper(II)-coated magnetic core-shell nanoparticles Fe3O4@SiO2-2-aminobenzohydrazide and investigation of its catalytic application in the synthesis of 1,2,3-triazole compounds

2021 ◽  
Vol 11 (1) ◽  
Author(s):  
H. Rajabi-Moghaddam ◽  
M. R. Naimi-Jamal ◽  
M. Tajbakhsh
Keyword(s):  
High Efficiency ◽  
Click Reaction ◽  
Magnetic Core ◽  
Core Shell ◽  
Isatoic Anhydride ◽  
Shell Nanoparticles ◽  
Triazole Derivatives ◽  
Catalytic Application ◽  
Ft Ir ◽  
Core Shell Nanoparticles

AbstractIn the present work, an attempt has been made to synthesize the 1,2,3-triazole derivatives resulting from the click reaction, in a mild and green environment using the new copper(II)-coated magnetic core–shell nanoparticles Fe3O4@SiO2 modified by isatoic anhydride. The structure of the catalyst has been determined by XRD, FE-SEM, TGA, VSM, EDS, and FT-IR analyzes. The high efficiency and the ability to be recovered and reused for at least up to 6 consecutive runs are some superior properties of the catalyst.

ChemInform Abstract: Novel Sesquiterpenes from Schisandra grandiflora: Isolation, Cytotoxic Activity and Synthesis of Their Triazole Derivatives Using “click” Reaction.

ChemInform ◽  
2015 ◽  
Vol 46 (26) ◽  
pp. no-no
Author(s):  
B. Poornima ◽  
Bandi Siva ◽  
G. Shankaraiah ◽  
A. Venkanna ◽  
V. Lakshma Nayak ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
Click Reaction ◽  
Triazole Derivatives

Design, synthesis and metal sensing studies of ether-linked bis-triazole derivatives

2015 ◽  
Vol 39 (5) ◽  
pp. 3777-3784 ◽  
Author(s):  
Arasappan Hemamalini ◽  
Sathish Kumar Mudedla ◽  
Venkatesan Subramanian ◽  
Thangamuthu Mohan Das
Keyword(s):  
Click Reaction ◽  
Spectroscopic Techniques ◽  
Computational Studies ◽  
Design Synthesis ◽  
Triazole Derivatives ◽  
Metal Sensing

Ether-linked-bis-triazole derivatives have been synthesized by (CuAAC) “Click” reaction. Interaction of the compound with Hg2+has been demonstrated by various spectroscopic techniques which was further confirmed with computational studies.

scholarly journals Synthesis, Biological Activity, and Molecular Modeling Studies of Pyrazole and Triazole Derivatives as Selective COX-2 Inhibitors

2020 ◽  
Vol 2020 ◽  
pp. 1-14 ◽  
Author(s):  
Mohyeddin Assali ◽  
Murad Abualhasan ◽  
Hadeel Sawaftah ◽  
Mohammed Hawash ◽  
Ahmed Mousa
Keyword(s):  
Aromatic Ring ◽  
Inhibitory Activity ◽  
Click Reaction ◽  
Docking Study ◽  
The Other ◽  
Synthetic Approach ◽  
Triazole Derivatives ◽  
Cox 2 ◽  
Cox 2 Inhibitors

Series of diaryl-based pyrazole and triazole derivatives were designed and synthesized in a facile synthetic approach in order to produce selective COX-2 inhibitor. These series of derivatives were synthesized by different reactions like Vilsmeier–Haack reaction and click reaction. In vitro COX-1 and COX-2 inhibition studies showed that five compounds were potent and selective inhibitors of the COX-2 isozyme with IC50 values in 0.551–0.002 μM range. In the diarylpyrazole derivatives, compound 4b showed the best inhibitory activity against COX-2 with IC50 = 0.017 μM as one of the N-aromatic rings was substituted with sulfonamide and the other aromatic ring was unsubstituted. However, when the N-aromatic ring was substituted with sulfonamide and the other aromatic ring was substituted with sulfone (compound 4d), best COX-2 selectivity was achieved (IC50 = 0.098 μM, SI = 54.847). In the diaryltriazole derivatives, compound 15a showed the best inhibitory activity in comparison to all synthesized compounds including the reference celecoxib with IC50 = 0.002 μM and SI = 162.5 as it could better fit the extra hydrophobic pocket which is present in the COX-2 enzyme. Moreover, the docking study supports the obtained SAR data and binding similarities and differences on both isozymes.

Novel sesquiterpenes from Schisandra grandiflora: Isolation, cytotoxic activity and synthesis of their triazole derivatives using “click” reaction

2015 ◽  
Vol 92 ◽  
pp. 449-458 ◽  
Author(s):  
B. Poornima ◽  
Bandi Siva ◽  
G. Shankaraiah ◽  
A. Venkanna ◽  
V. Lakshma Nayak ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
Click Reaction ◽  
Triazole Derivatives

scholarly journals Experimental and Theoretical DFT Investigations in the [2,3]-Wittig-Type Rearrangement of Propargyl/Allyl-Oxy-Pyrazolones

Molecules ◽  
2021 ◽  
Vol 26 (21) ◽  
pp. 6557
Author(s):  
Lucia De Crescentini ◽  
Gianfranco Favi ◽  
Giacomo Mari ◽  
Gianluca Ciancaleoni ◽  
Marcello Costamagna ◽  
...  
Keyword(s):  
Allyl Alcohol ◽  
Propargyl Alcohol ◽  
Dft Study ◽  
Nucleophilic Attack ◽  
Wittig Rearrangement ◽  
Reaction Proceeds

Here we report the synthesis of interesting 3-alkyl-4-hydroxy-1-aryl-4-(propa-1,2-dienyl)1H-pyrazol-5(4H)-ones and 9-alkyl-7-aryl-1-oxa-7,8-diazaspiro[4.4]nona-3,8-dien-6-ones, starting from 1,2-diaza-1,3-dienes (DDs) and propargyl alcohol. The reaction proceeds through a sequence Michael-type nucleophilic attack/cyclization/[2,3]-Wittig rearrangement. In the same way, the reaction between the aforementioned DDs and allyl alcohol furnished 4-allyl-4-hydroxy-3-alkyl-1-aryl-1H-pyrazol-5(4H)-ones. A DFT study was also carried out, in order to have decisive clarifications about the mechanism.

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