Sequential one-pot three-step synthesis of polysubstituted 4-(5-(trifluoromethyl)-1H-pyrazol-4-yl)-1H-1,2,3-triazole systems

Bonacorso, Hélio G.; Forno, Gean M. Dal; Wiethan, Carson W.; Ketzer, Alex; Zanatta, Nilo; Frizzo, Clarissa P.; Martins, Marcos A. P.; Stradiotto, Mark

doi:10.1039/c7ra07960e

Cited by 12 publications

(5 citation statements)

References 32 publications

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“…The subsequent fluoride-mediated cleavage of the TMS group and click reaction with azides gave fluorinated pyrazoles of type 519. 209 In 2017, Itami and Torii reported the discovery of small synthetic molecules that enhance a number of stomata. 210 pyrazoles 520 with substituted aryl bromides (Scheme 88).…”

Section: Derivatizations Of Fluorinated Pyrazolesmentioning

confidence: 99%

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Fluorinated Pyrazoles: From Synthesis to Applications

2020

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Fluorinated pyrazoles play an important role in medicinal chemistry, drug discovery, agrochemistry, coordination chemistry, and organometallic chemistry. Since the early 1990s, their popularity has grown exponentially. Moreover, more than 50% of all contributions on the topic have been published in the last 5 years. In this review, analysis of novel synthetic approaches to fluorinated pyrazoles that appeared in recent years is performed. A particular emphasis is devoted to a detailed consideration of reaction mechanisms. In addition, the reasons that have led to the ever-increasing popularity of fluorinated pyrazoles in various areas of science are discussed. At the end of the review, several potentially interesting but yet mostly unknown classes of fluorinated pyrazoles are outlined.

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Section: Derivatizations Of Fluorinated Pyrazolesmentioning

confidence: 99%

“…In the following year, the authors performed a Sonogashira coupling of bromopyrazoles with alkyne 518 (Scheme ). The subsequent fluoride-mediated cleavage of the TMS group and click reaction with azides gave fluorinated pyrazoles of type 519 …”

Section: Preparation Of Fluoroalkyl-substituted Pyrazolesmentioning

confidence: 99%

Fluorinated Pyrazoles: From Synthesis to Applications

2020

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“…The structures of 6-aminoquinolines 4a-f were characterized by 1 H-, 13 C-, and 19 F-NMR spectroscopy and GC-MS techniques, and also compared with reported data of similar compounds. 22,[35][36][37] It is reported that the synthesis of quinolines can lead to a mixture of two types of isomers (2-CF 3 and 4-CF 3 ) when the reaction involves the use of anilines with 1,3-dicarbonyl compounds in acid medium. 38,39 However, our research group recently reported Scheme 1 Synthesis of 6-amino-4-(trifluoromethyl)quinolines 4. a successful regioselective intramolecular cyclization reaction that enabled the isolation of the 4-CF 3 isomer.…”

Section: Synthesismentioning

confidence: 99%

Synthesis and photophysical, thermal and antimycobacterial properties of novel 6-amino-2-alkyl(aryl/heteroaryl)-4-(trifluoromethyl) quinolines

et al. 2019

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“…AB1 and AB2 molecules were synthesized using the reaction pathway in Scheme 1 [45][46][47][48]. First of all, pyrazole derivatives were synthesized from acetylacetone (1 ).…”

Section: Synthesismentioning

confidence: 99%

Prediction of the Charge Transport and Electronic Properties of Two Pyrazole Derivatives in terms of Their Solid Molecular Arrangements and Reorganization Energy: The Effects of Nitro Groups on Structure-Property Relationship

Biçer

Cin

Yakalı

2022

Preprint

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Pyrazole derivatives have noteworthy attention in optoelectronic field since they demonstrate distinctive properties in semiconducting devices such as organic light emitting diodes (OLEDs), nonlinear optical (NLO) and solar cells. organic field effect transistors (OFETs). Therefore, to establish the relationship between the structure and property of the molecules, we explored influence of nitro groups on the 3D molecular structures, reorganization energy, absorption spectra, frontier orbitals, ionization potential (IP), electronic affinity (EA), intra-molecular charge transfer (ICT) and charge transport behaviour of the two π-conjugated pyrazole compunds through single crystal x-ray crystallographic and quantum chemical calculations by considering Marcus Electron Transfer Theory and Density Functional Theory. Our experimental and theoretical results predicted that incorporation of the nitro groups to the molecule skeleton increased the rigidity of the conjugated system and improve the efficient charge injection in electronic devices by lowering the hole (λ_h) and electron (λ_e) reorganization energy from 0.48eV to 0.34 eV, 0.44 eV to 0.26 eV, respectively which can be effective way to design molecules with desired electronic properties via smart chemical structural modification. In addition, both molecules aggregate with the close preferred π⋯π stacking interactions (J and antiparallel H type) and multiple intermolecular interactions in their solid phases. Accordingly, both molecules are suggested to be quite suitable for p-type semiconducting materials with small reorganization energy and preferred stacking modes in solid phase. In addition, this study paves the way for the design and synthesis of new conjugated pyrazole molecules for high device performance.

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Sequential one-pot three-step synthesis of polysubstituted 4-(5-(trifluoromethyl)-1H-pyrazol-4-yl)-1H-1,2,3-triazole systems

Abstract: Sequential one-pot, three-step synthesis of polysubstituted 4-(5-(trifluoromethyl)-1H-pyrazol-4-yl)-1H-1,2,3-triazoles.

Cited by 12 publications

References 32 publications

Fluorinated Pyrazoles: From Synthesis to Applications

Fluorinated Pyrazoles: From Synthesis to Applications

Synthesis and photophysical, thermal and antimycobacterial properties of novel 6-amino-2-alkyl(aryl/heteroaryl)-4-(trifluoromethyl) quinolines

Prediction of the Charge Transport and Electronic Properties of Two Pyrazole Derivatives in terms of Their Solid Molecular Arrangements and Reorganization Energy: The Effects of Nitro Groups on Structure-Property Relationship

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