An approach to the synthesis of 3-substituted piperidines bearing partially fluorinated alkyl groups

Subota, Andrii I.; Gorlova, Alina O.; Grygorenko, Oleksandr O.; Volochnyuk, Dmitriy M.

doi:10.1016/j.jfluchem.2019.05.006

Cited by 8 publications

(2 citation statements)

References 27 publications

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“…17,[40][41][42][43] To the best of our knowledge, synthetic utility of alkoxyvinyl glyoxylates for the construction of fused pyridines was not demonstrated to date. In continuation of our work in the field of pyridine chemistry, [44][45][46][47][48][49][50] we have now aimed at the study of the low-molecular-weight alkoxyvinyl glyoxylates 11a-c as CCC bis-electrophiles in the reactions with common NCC binucleophiles 9 (Scheme 1).…”

Section: Syn Thesismentioning

confidence: 99%

Synthesis of Fused Pyridine Carboxylates by Reaction of β-Alkoxyvinyl Glyoxylates with Amino Heterocycles

et al. 2020

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An efficient approach to the preparation of pyridine carboxylates fused with 5- or 6-membered heteroaromatic rings is described. The method relied on the Combes-type condensation of the low-molecular-weight β-alkoxyvinyl glyoxylates as CCC bis-electrophiles and with heteroaromatic amines as NCC binucleophiles. In most experiments, β-alkoxyvinyl glyoxylates without additional substituent at the β position led to the corresponding α-pyridine carboxylates (67–87% yield). In the case of β-methyl-substituted derivative, γ-pyridine carboxylates were obtained in 84–99% yield. It was found that regioselectivity of the condensation could be efficiently tuned by changing conditions, such as solvents and acidic additives (HOAc, DMSO or HCl–1,4-dioxane).

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Section: Syn Thesismentioning

confidence: 99%

Synthesis of Fused Pyridine Carboxylates by Reaction of β-Alkoxyvinyl Glyoxylates with Amino Heterocycles

et al. 2020

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“…The corresponding transformation of less active acetophenones is also known, but often problematic, however . There are many precedents in the literature on deoxofluorination of five- and six-membered heteroaromatic alkyl ketones with DAST ( 4 ) morph-DAST ( 5 , O(CH 2 CH 2 ) 2 NSF 3 ) or its analogues, yet these examples are not systematic and are often a result of individual extensive optimization. − For example, previously our colleagues synthesized pyridine 6a from ketone 6 and DAST (8 equiv) in 40% yield . The reaction was slowit took place during 14 days.…”

Section: Introductionmentioning

confidence: 99%

Scalable Approach to Fluorinated Heterocycles with Sulfur Tetrafluoride (SF₄)

et al. 2021

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A general approach to fluorinated (hetero)aromatic derivatives is elaborated. The key reaction is a deoxofluorination of substituted acetophenones with sulfur tetrafluoride (SF 4 ). In contrast to previous deoxofluorination methods, this transformation is fast, scalable (up to 70 g), and high-yielding. More than 100 novel or previously hardly accessible fluorinated heterocycles, interesting for medicinal chemistry and agrochemistry, were synthesized.

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Synthesis and chemical transformations of diazolyl α,α-difluoroacetates

Geraschenko

Solomin

Vashchenko

et al. 2020

Journal of Fluorine Chemistry

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An approach to the synthesis of 3-substituted piperidines bearing partially fluorinated alkyl groups

Cited by 8 publications

References 27 publications

Synthesis of Fused Pyridine Carboxylates by Reaction of β-Alkoxyvinyl Glyoxylates with Amino Heterocycles

Synthesis of Fused Pyridine Carboxylates by Reaction of β-Alkoxyvinyl Glyoxylates with Amino Heterocycles

Scalable Approach to Fluorinated Heterocycles with Sulfur Tetrafluoride (SF₄)

Synthesis and chemical transformations of diazolyl α,α-difluoroacetates

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An approach to the synthesis of 3-substituted piperidines bearing partially fluorinated alkyl groups

Cited by 8 publications

References 27 publications

Synthesis of Fused Pyridine Carboxylates by Reaction of β-Alkoxyvinyl Glyoxylates with Amino Heterocycles

Synthesis of Fused Pyridine Carboxylates by Reaction of β-Alkoxyvinyl Glyoxylates with Amino Heterocycles

Scalable Approach to Fluorinated Heterocycles with Sulfur Tetrafluoride (SF4)

Synthesis and chemical transformations of diazolyl α,α-difluoroacetates

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Scalable Approach to Fluorinated Heterocycles with Sulfur Tetrafluoride (SF₄)