Synthesis of 4-amino-5-fluoropyrimidines and 5-amino-4-fluoropyrazoles from a β-fluoroenolate salt

Lucas, Tobias; Dietz, Jule‐Philipp; Opatz, Till

doi:10.3762/bjoc.16.41

Cited by 3 publications

(3 citation statements)

References 37 publications

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“…In 2020, Opatz synthesized fluoro-substituted salt 44 in three steps from chloroacetamide (45) in 42% yield (Scheme 8). 44 Condensation of compound 44 with hydrazines afforded 4fluoro-5-aminopyrazoles of type 46−48 in 20−46% yield.…”

Section: Oxidative Fluorination Of Pyrazolesmentioning

confidence: 99%

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: Oxidative Fluorination Of Pyrazolesmentioning

confidence: 99%

Fluorinated Pyrazoles: From Synthesis to Applications

2020

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“…Thus, the reaction of fluoroacetonitrile with ethyl formate in the presence of KOBu t gave potassium (Z)-2-cyano-2-fluoroethenolate (360) (77%) (Scheme 141), 35 an attractive and readily available building-block for the synthesis of fluorinated heterocycles such as fluorinated pyrimidines and pyrazoles. 151 The approach was expanded by using of various bases such as KOBu t , NaOBu t , NaOAmyl t , NaHMDS, and methyl/ethyl formates, that allowed preparation of sodium and potassium (Z)-2cyano-2-fluoroethenolates in 35-79% yield. No target product was isolated when such bases as NaOMe, NaH, KOEt were used.…”

Section: R F -Nitriles As Active Methylene Compoundsmentioning

confidence: 99%

Chemistry of fluoroalkyl cyanides

Usachev¹

2020

Arkivoc

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This review is devoted to the chemistry of fluoroalkyl cyanides (R F -nitriles): their synthesis and chemical properties. Syntheses of non-functionalized R F -nitriles (FCH 2 CN, F 2 CHCN, CF 3 CN, C 2 F 5 CN, FCH 2 CH 2 CN, etc.) and dinitriles (NCCHFCN, NCCF 2 CN, NCCF 2 CF 2 CN, etc.) are considered. The synthesis of functionalized R F -nitriles such as F 2 NCF 2 CN, F 2 NCClFCN, Cl 2 CFCN, Br 2 CFCN, (O 2 N) 2 CFCN, O 2 NCF 2 CH 2 CH 2 CN, and dinitriles, such as O(CF 2 CN) 2 , NCCF 2 N=NCF 2 CN, is also considered. R F -Nitriles are attractive electrophilic, enophilic, and dienophilic building-blocks: they were used in the synthesis of various fluorine-containing heterocyclic compounds, such as R F -bearing pyridines, 1,3,5-triazines, tetrazoles, and others. R F -nitriles were also used in the synthesis of unusual acyclic compounds, such as fluoroalkylated N,N-difluoroamines, F 2 NCF 2 CF 2 N=SF 2 , R Fimino esters, and others.

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“…Thus, MCR approach has gained significant popularity in the fields of pharmaceutical chemistry and drug development, including control of stereo isomers [38]. In the sequence of the reaction, intercoordination between the reactants, solvent and catalyst is crucial for the success of MCRs [39]. Consequently, with choice for diverse molecular entities as reactants, MCRs have cherished in the designing of different organic blocks to prepare various fascinating heterocyclic frameworks [40].…”

Section: Introductionmentioning

confidence: 99%

review on green multicomponent synthesis of heterocyclic compounds

D’souza

D’Souza

Mendonca

et al. 2022

ijhs

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Heterocyclic compounds are of very much concern in our daily life. These compounds constitute the largest and most varied family of organic compounds. Heterocyclic compounds have one or more hetero atoms in their structure., Day by day the number is increasing rapidly due to the enormous synthetic research and also their synthetic utility. They may be cyclic or non-cyclic in nature. They are predominantly used as pharmaceuticals, as agrochemicals and as veterinary products. They also find applications as sanitizers, developers, antioxidants, as corrosion inhibitors, as copolymers, dye stuff and anticancer drugs. They are used as vehicles in the synthesis of other organic compounds. In this review, we cover most biological active heterocyclic compounds that it’s recently synthesized or extracted from the plants e.g. antibiotics such as penicillin’s, cephalosporin; alkaloids such as vinblastine, morphine, reserpine etc. have heterocyclic moiety.

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Synthesis of 4-amino-5-fluoropyrimidines and 5-amino-4-fluoropyrazoles from a β-fluoroenolate salt

Cited by 3 publications

References 37 publications

Fluorinated Pyrazoles: From Synthesis to Applications

Fluorinated Pyrazoles: From Synthesis to Applications

Chemistry of fluoroalkyl cyanides

review on green multicomponent synthesis of heterocyclic compounds

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