Synthesis of trifluoromethylated isoxazoles and their elaboration through inter- and intra-molecular C–H arylation

Poh, Jian‐Siang; García‐Ruiz, Cristina; Zúñiga, Andrea; Meroni, Francesca; Blakemore, David C.; Browne, Duncan L.; Ley, Steven V.

doi:10.1039/c6ob00970k

Cited by 39 publications

(13 citation statements)

References 63 publications

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“…Under basic conditions bromide was transformed into nitrile oxide on reaction with the terminal alkynes to form the respective 3‐trifluoromethyl‐5‐substituted isoxazoles ( 176 ) in excellent yields (Scheme 30). [72] …”

Section: Five‐membered Heterocycle Having Nitrogen and Oxygen Atomsmentioning

confidence: 99%

Recent advances in the synthesis of five‐ and six‐membered heterocycles as bioactive skeleton: A concise overview

et al. 2022

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Heterocyclic compounds play a tremendous role in the field of medicinal chemistry due to their association with diverse pharmacological properties. Most of the pharmaceutical drugs used in medicines possess a wide range of heterocyclic nucleus. It was decided basis on literature studies that various synthetic protocols like microwave‐assisted, nanocatalysed, green synthesis, click reaction, and multicomponent routes could be used for the betterment of the purity of products, selectivity, and better yields of the products. We have focused attention on the development of synthetic strategies of the above‐mentioned moieties because N‐, O‐ and S‐ containing heterocyclic compounds have seemed owing to a wide diversity of their biological activities viz. antioxidant, anticancer, anticonvulsant, anti‐inflammatory, neuroprotective, antiproliferative, anti‐obesity, antihyperglycemic, antihypercholesteroler, antiulcer, antidiabetic, antileishmanial, antitrypanosomal, antibiotic, etc. In this review article, an overview of the applications of synthetic protocols for the preparation of five‐membered and six‐membered heterocyclic compounds containing two or more heteroatoms (O, N, S) at different‐different positions along with their different potent and competent candidates against various diseases is presented in last 10–15 years.

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Section: Five‐membered Heterocycle Having Nitrogen and Oxygen Atomsmentioning

confidence: 99%

Recent advances in the synthesis of five‐ and six‐membered heterocycles as bioactive skeleton: A concise overview

et al. 2022

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“…The use of triarylphosphines as ligands in the intramolecular CÀ H arylation reaction was found to be critical in reducing the reaction temperature, time and this led to an increase in the reaction yield. [24] Scheme 13. Pd-catalyzed C4 arylation of 3,5-disubstituted isoxazoles with aryl chlorides.…”

Section: C-4 Arylationmentioning

confidence: 99%

Transition Metal‐Mediated Functionalization of Isoxazoles: A Review

2021

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Isoxazoles are an important class of heterocycles with nitrogen and oxygen in a 1,2-relationship. They find wide applications in synthetic organic chemistry and are part of several drug molecules. Since the last two decades, great progress has been achieved in the synthesis and functionalization of isoxazoles, in which transition metal catalysis played a pivotal role towards achieving this goal. In particular, the transition metal (TM)-mediated site-selective functionalizations of isoxazoles which retain the pharmacologically and synthetically valuable isoxazole skeleton, are highly appealing. This comprehensive review is solely dedicated to the TM-mediated functionalization of isoxazoles, wherein we have included isoxazoles as directing groups (DG) for TM-catalyzed CÀ H functionalization reactions, TM-catalyzed direct CÀ H functionalization, along with cross-coupling reactions of isoxazoles, TM-catalyzed annulation reactions of isoxazoles and finally ring-opening reactions of isoxazoles under TMcatalysis are also discussed. Also, incorporated are discussions on reaction designs, their advantages and limitations, mechanistic details and challenges that need to be addressed to inspire synthetic organic and medicinal chemists to explore new reaction arenas and make use of this key scaffold.Scheme 1. Synthetic approaches for functionalized isoxazoles.Scheme 2. Functionalization of isoxazoles via the 4-isoxazolyl anion species.

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“…(3-(Trifluoromethyl)isoxazol-5-yl)methanol (20b). 20 Yield 70.1 g (93%) from 120 g of 13b. Colorless liquid, bp = 49−52 °C/ 1 mbar.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Regioselective Synthesis of Functionalized 3- or 5-Fluoroalkyl Isoxazoles and Pyrazoles from Fluoroalkyl Ynones and Binucleophiles

et al. 2019

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A facile synthetic route toward either 3- or 5-fluoroalkyl-substituted isoxazoles or pyrazoles containing an additional functionalization site was developed and applied on a multigram scale. The elaborated approach extends the scope of fluoroalkyl substituents for introduction into the heterocyclic moiety, and uses convenient transformations of the side chain for incorporation of fluoroalkyl-substituted azoles into the structures of biologically active molecules. The utility of the obtained building blocks for isosteric replacement of alkyl-substituted isoxazole and pyrazole was shown by the synthesis of fluorinated Isocarboxazid and Mepiprazole analogues.

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Synthesis of trifluoromethylated isoxazoles and their elaboration through inter- and intra-molecular C–H arylation

Cited by 39 publications

References 63 publications

Recent advances in the synthesis of five‐ and six‐membered heterocycles as bioactive skeleton: A concise overview

Recent advances in the synthesis of five‐ and six‐membered heterocycles as bioactive skeleton: A concise overview

Transition Metal‐Mediated Functionalization of Isoxazoles: A Review

Regioselective Synthesis of Functionalized 3- or 5-Fluoroalkyl Isoxazoles and Pyrazoles from Fluoroalkyl Ynones and Binucleophiles

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