One-step synthesis of polypyrazoles and self-assembled polypyrazole–copper catalysts for click chemistry

Xiao, Longqiang; Cai, Shaojun; Liu, Qingye; Liao, Liqiong; Guo, Xin; Li, Yan; Jia, Xiangxiang; Li, Feifei; Liu, Lijian

doi:10.1039/c3py01105d

Cited by 14 publications

(9 citation statements)

References 41 publications

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“…Reactions of bis-nitrilimines 3 , bis-sydnones 4 and bis-azides 5 with diacetylenes have been used successfully to produce the polypyrazoles. In recent year, it was also successfully produced via click reaction of diazos with diacetyelenes 6 . In addition, Bass and coworkers have used the reactions of bis-hydrazines with acetylenic ketones and esters to prepare thermally stable polypyrazoles 7 .…”

Section: Introductionmentioning

confidence: 99%

“…Moreover, polyisoxazoles were successfully synthesized by click reaction in one-pot manner in our laboratory 20 , which benefited from the high efficiency and regioselectivity of click chemistry. Polypyrazoles are also important heterocyclic polymers and they can be synthesized by click reactions 6 . Inspired by these advances, we investigated the regioselective synthesis of 3,5-disubstituted polypyrazoles by a one-pot three-step process.…”

Section: Introductionmentioning

confidence: 99%

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One-Pot Synthesis of Polypyrazoles by Click Reactions

Wang

Chen

2017

Sci Rep

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AbastractWe developed an efficient one-pot metal-free click polymerization procedure for the synthesis of 3,5-disubstituted polypyrazoles with high yields, high molecular weights, and narrow molecular weight distribution. The method involved two click reactions in a one-pot synthesis. The first reaction was the carbonyl chemistry of “non-aldol” type (condensation reaction of aldehydes with p-toluenesulfonylhydrazide), and the second was a click polymerization reaction of diazo compounds with alkynes. The reactions occurred sequentially by adding the reactants step by step. The diazo compound needed for the second click reaction was generated in situ by the first click reaction. The structures of the polypyrazoles were characterized by IR and 1H NMR analyses. And their thermal properties and solubility were also tested.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

One-Pot Synthesis of Polypyrazoles by Click Reactions

Wang

Chen

2017

Sci Rep

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“…Pyrazole is another important heterocyclic with wide applications as blue fluorophores, optical brighteners, ligands for metal–organic frameworks, building blocks for liquid crystalline displays, and intermediates for biological molecules . Polypyrazoles are also promising materials with potential blue emission; , however, there are still lack of efficient synthetic methods. , Alkynone can react with hydrazines to form pyrazole rings after cascade addition–cyclocondensation reactions (Scheme ). A similar strategy of combining Sonogashira coupling–Michael addition–cyclocondensation reactions is adopted to synthesize multisubstituted pyrazoles in good to excellent yields in moderate condition with good regioselectivity and wide substrate applicability. , …”

Section: Introductionmentioning

confidence: 99%

“…28 Polypyrazoles are also promising materials with potential blue emission; 29,30 however, there are still lack of efficient synthetic methods. 31,32 Alkynone can react with hydrazines to form pyrazole rings after cascade addition− cyclocondensation reactions (Scheme 1). 33 A similar strategy of combining Sonogashira coupling−Michael addition−cyclocondensation reactions is adopted to synthesize multisubstituted pyrazoles in good to excellent yields in moderate condition with good regioselectivity and wide substrate applicability.…”

Section: ■ Introductionmentioning

confidence: 99%

Multicomponent Tandem Polymerizations of Aromatic Diynes, Terephthaloyl Chloride, and Hydrazines toward Functional Conjugated Polypyrazoles

et al. 2016

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Multicomponent tandem polymerizations (MCTPs) of alkynes enjoying concise procedure, operational simplicity, synthetic efficiency, large structural diversity, high atom economy, and environmental benefit are recently developed as efficient strategies to synthesize functional conjugated polymers, which have attracted much attention from polymer scientists. In this work, through combination of Sonogashira coupling–Michael addition–cyclocondensation reactions in a one-pot procedure, an efficient three-component tandem polymerization of alkyne, carbonyl chloride, and hydrazine hydrate was reported to proceed smoothly under mild conditions at room temperature, affording polypyrazoles with high molecular weights (M w up to 19 400 g/mol) in excellent yields (up to 95%). This MCTP also applies to various aromatic diynes and aromatic hydrazines, producing polypyrazoles with improved solubility and processability, higher M ws of up to 30 700 g/mol, and high yields. Structural characterization of the polymers such as IR, 1H NMR, and 13C NMR spectra suggested total consumption of monomers and complete conversion of the polymer intermediate, proving the desired well-defined structure of polypyrazoles. These polypyrazoles generally enjoy good solubility and film-forming ability, high thermal stability, high light refractivity, and luminescence behavior. Such MCTPs are not just a simple reaction to connect functional units together in a polymer chain; they can also build functional units such as the newly formed multisubstituted heterocyclics embedded in the polymer main chain at the same time.

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“…(2-oxo-2-phenylethyl)-1H-1,2,3-triazole-4-carboxylate (6a)[43].Methyl 1-(2-ethoxy-2-oxoethyl)-1H-1,2,3-triazole-4-carboxylate (12b)[44]. Colorless solid, purified by recrystallization from ethanol/hexanes.…”

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confidence: 99%

Regioselective Reduction of 1H-1,2,3-Triazole Diesters

2021

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Regioselective reactions can play pivotal roles in synthetic organic chemistry. The reduction of several 1-substituted 1,2,3-triazole 4,5-diesters by sodium borohydride has been found to be regioselective, with the C(5) ester groups being more reactive towards reduction than the C(4) ester groups. The amount of sodium borohydride and reaction time required for reduction varied greatly depending on the N(1)-substituent. The presence of a β-hydroxyl group on the N(1)-substituent was seen to have a rate enhancing effect on the reduction of the C(5) ester group. The regioselective reduction was attributed to the lower electron densities of the C(5) and the C(5) ester carbonyl carbon of the 1,2,3-triazole, which were further lowered in cases involving intramolecular hydrogen bonding.

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One-step synthesis of polypyrazoles and self-assembled polypyrazole–copper catalysts for click chemistry

Cited by 14 publications

References 41 publications

One-Pot Synthesis of Polypyrazoles by Click Reactions

One-Pot Synthesis of Polypyrazoles by Click Reactions

Multicomponent Tandem Polymerizations of Aromatic Diynes, Terephthaloyl Chloride, and Hydrazines toward Functional Conjugated Polypyrazoles

Regioselective Reduction of 1H-1,2,3-Triazole Diesters

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