Synthesis and antimicrobial activity of new aldehydes and acetals

Keiko, N. A.; Степанова, Л. Г.; Kleptsova, E. A.; Vdovina, G. P.; Одегова, Т. Ф.

doi:10.1007/s11094-009-0339-3

Cited by 5 publications

(2 citation statements)

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“…Bromoacetaldehyde diethyl acetal (1) is commercially available and can be prepared by several procedures: from diethylacetal 2 and bromosuccinimide, 6 from vinyl acetate 3 with bromine in ethanol, 7 and from 2,4,6-trimethyl-1,3,5-trioxane 4 with bromine in ethanol. 8 (B) Diaryl-1,2,4-triazoles 11 bearing an N-hydroxyurea moiety can be obtained in a reaction sequence beginning with the preparation of oxime 9 from bromoacetal 1, followed by the bromide displacement in 9 after reaction with the thiol 10, and a two-step installation of a carbamoyl fragment.…”

Section: Preparationmentioning

confidence: 99%

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Bromoacetaldehyde Diethyl Acetal

Gotkowska

2015

Synlett

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Section: Preparationmentioning

confidence: 99%

Section: Preparationmentioning

confidence: 99%

Bromoacetaldehyde Diethyl Acetal

Gotkowska

2015

Synlett

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Dihydropyrans by Cycloadditions of Oxadienes

et al. 2020

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3,4‐Dihydro‐2H‐pyrans are present in the skeletons of several natural products, and these versatile synthetic intermediates are readily transformed into tetrahydropyrans, pyridines, or 1,5‐dicarbonyl units. Among the strategies developed to access 3,4‐dihydro‐2H‐pyrans, the hetero‐Diels‐Alder reaction between an oxadiene and a dienophile is particularly valuable because up to three contiguous stereogenic centers can be created diastereo‐ and/or enantioselectively in a single step. This review addresses the mechanism of the reaction and presents methods for preparing the product dihydropyrans enantio‐ and diastereoselectively. Thermal and Lewis acid promoted cycloadditions are discussed, as is the role of activating groups on the oxadiene.

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Hydroformylation of Alkynyl Sulfides: A Stereo‐ and Regioselective Route to α‐Sulfenyl Acroleins

Wagner,

Gulea,

Girard

2024

Adv Synth Catal

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The rhodium‐catalyzed hydroformylation of alkynyl sulfides under mild conditions is described. The method gives access to α‐sulfenyl acroleins with good regioselectivities (ratio α/β up to 89/11) and is applicable to variously substituted substrates. It is effective even on more complex substrates, such as cysteine and cholesterol derivatives. To demonstrate the synthetic potential of the obtained products, (Z)‐3‐cyclohexyl‐2‐methylsulfenyl acrolein was selected as an example and its sulfur atom selectively oxidized to the corresponding sulfoxide or sulfone. Acid‐promoted (Z) to (E) isomerization of the double bond occurred during oxidation. The three obtained sulfenyl‐, sulfinyl‐, and sulfonyl‐functionalized acroleins have been then used as dienophiles to access cyclohexene carbaldehydes.

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Synthesis and antimicrobial activity of new aldehydes and acetals

Abstract: Methods for the synthesis of new aldehydes and acetals have been developed. The antimicrobial activity of the synthesized compounds against Staphylococcus aureus and Escherichia coli was estimated.

Cited by 5 publications

References 1 publication

Bromoacetaldehyde Diethyl Acetal

Bromoacetaldehyde Diethyl Acetal

Dihydropyrans by Cycloadditions of Oxadienes

Hydroformylation of Alkynyl Sulfides: A Stereo‐ and Regioselective Route to α‐Sulfenyl Acroleins

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