Synthesis of bromocyclopropylpyridines via the Sandmeyer reaction

Striela, Romualdas; Urbelis, Gintaras; Sūdžius, Jurgis; Stončius, Sigitas; Sadzevičienė, Rita; Labanauskas, Linas

doi:10.1016/j.tetlet.2017.03.029

Cited by 5 publications

(4 citation statements)

References 10 publications

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“…During our custom synthesis projects related to the production of various building blocks containing cyclopropylbenzene, amino-and bromocyclopropylpyridine [20] moieties, we successfully applied a catalytic system developed by Buchwald [21]. The palladium (II) acetate and dicyclohexyl(2 ,6 -dimethoxy [1,1 -biphenyl]-2-yl)phosphane (SPhos) ligand's system allows the use of small catalyst loading for the Suzuki-Miyaura cross-coupling reactions.…”

Section: Resultsmentioning

confidence: 99%

Palladium-Catalyzed Synthesis of Cyclopropylthiophenes and Their Derivatization

et al. 2023

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The cyclopropylthiophene moiety has attracted the attention of the scientific community for its potential pharmaceutical applications. However, synthesis of the compounds containing this framework remains challenging, has rarely been reported and remains unresolved. Here we provide optimized syntheses for cyclopropylthiophenes and their derivatives, containing carbonyl, acetyl, carboxylic acid, methyl carboxylate, nitrile, bromide and sulfonyl chloride moieties.

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Section: Resultsmentioning

confidence: 99%

Palladium-Catalyzed Synthesis of Cyclopropylthiophenes and Their Derivatization

et al. 2023

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“…Compound 3p was synthesized using 5-cyclopropylpyridin-2-amine (40 mg, 0.30 mmol), 22 picolinaldehyde (64 mg, 0.60 mmol), and 2a (72 mg, 0.60 mmol) according to General Procedure B. The crude product was purified by reverse phase chromatography (50–70% MeOH:H 2 O) to provide a beige solid (33 mg, 32%).…”

Section: Methodsmentioning

confidence: 99%

Structure–Property Optimization of a Series of Imidazopyridines for Visceral Leishmaniasis

Dichiara,

Simpson,

Quotadamo

et al. 2023

ACS Infect. Dis.

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Leishmaniasis is a collection of diseases caused by more than 20 Leishmania parasite species that manifest as either visceral, cutaneous, or mucocutaneous leishmaniasis. Despite the significant mortality and morbidity associated with leishmaniasis, it remains a neglected tropical disease. Existing treatments have variable efficacy, significant toxicity, rising resistance, and limited oral bioavailability, which necessitates the development of novel and affordable therapeutics. Here, we report on the continued optimization of a series of imidazopyridines for visceral leishmaniasis and a scaffold hop to a series of substituted 2-(pyridin-2-yl)-6,7dihydro-5H-pyrrolo[1,2-a]imidazoles with improved absorption, distribution, metabolism, and elimination properties.

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“…Considering their importance, Striela et al . [ 41 ] prepared bromocyclopropylpyridines by the reaction of aminocyclopropylpyridines (obtained via Suzuki reaction of aminobromopyridines) with amyl nitrite through Sandmeyer approach. Reaction proceeded at room temperature in dibromomethane solvent using 0.5 equivalent CuBr 2 to obtain good yield range.…”

Section: Review Of Literature: Applications Of Sandmeyer Reactionmentioning

confidence: 99%

“…A variety of pharmaceutical agents having cyclopropylpyridine scaffold are good inhibitors of interleukin Scheme 11 Synthesis of pyrazoles by adopting Sandmeyer and Suzuki-Miyaura approaches Scheme 12 Facile synthesis of bromobenzene 60 by using Sandmeyer protocol receptor-associated kinases, PDE4 enzyme inhibitors and have been widely used to synthesize canabinoid receptor 2 agonists. Considering their importance, Striela et al [41] prepared bromocyclopropylpyridines by the reaction of aminocyclopropylpyridines (obtained via Suzuki reaction of aminobromopyridines) with amyl nitrite through Sandmeyer approach. Reaction proceeded at room temperature in dibromomethane solvent using 0.5 equivalent CuBr 2 to obtain good yield range.…”

Section: Bromination Via Sandmeyer Reactionmentioning

confidence: 99%