A convenient method for the preparation of chiral phosphonoacetamides and their Horner–Wadsworth–Emmons reaction

Ordóñez, Mario; Hernández-Fernández, Eugenio; Montiel‐Perez, Martin; Bautista, Rafael; Bustos, Paola; Rojas-Cabrera, Haydée; Fernández‐Zertuche, Mario; García-Barradas, Óscar

doi:10.1016/j.tetasy.2007.09.033

Cited by 18 publications

(3 citation statements)

References 86 publications

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“…The latter compound was made by the reaction of triethyl phosphite with bromo-N,N-dimethylacetamide as performed by Barlett et al with trimethyl phosphite. 44 Horner-Wadsworth-Emmons reactions using ylides stabilized by acetamido groups have been performed on a number of occasions, [45][46][47][48][49] but never with dialdehydes, as far as we are aware. The conjugated amides were obtained exclusively as trans alkenes, as established from the magnitudes of the 3 J H,H values across the alkene (16 Hz).…”

Section: Jocarticlementioning

confidence: 99%

Synthesis of Surfactants Based on Pentaerythritol. I. Cationic and Zwitterionic Gemini Surfactants

et al. 2009

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Simple strategies for the synthesis of five series of cationic gemini surfactants and one series of zwitterionic gemini surfactants from pentaerythritol have been developed. Two lipophilic groups were introduced onto pentaerythritol by alkylation of the known compound, O-benzylidenepentaerythritol, with 1-bromooctane, 1-bromodecane, 1-bromododecane, and 1-bromotetradecane. Hydrogenolysis of the benzylidene acetals gave diols which were converted into three different series of trimethylammonium derivatives. The diiodides derived from the diols could be displaced by dimethylamine, even though they are adjacent to a quaternary carbon atom. Alkylation with methyl iodide gave the first series. The iodides were easily displaced by cyanide ion and the resulting dinitriles were hydrolyzed, converted to N,N-dimethylamides, and reduced to give a second series. Oxidation of the diols to dialdehydes under Swern conditions followed by Horner−Wadsworth−Emmons reactions with diethyl N,N-dimethylcarbamoylmethylphosphonate followed by two-stage reduction gave a third series. The dialkoxides derived from the four di-O-alkylpentaerthritol diols were reacted with 2-dimethylaminoethyl chloride and 3-dimethylaminopropyl chloride in neighboring-group assisted double Williamson ether syntheses to give precursors to two more series. As expected because the neighboring group participation occurs through a four-membered-ring intermediate, considerably more vigorous conditions were required for the reactions with 3-dimethylaminopropyl chloride. 2-Diethylaminoethyl bromide was found to be less reactive than 2-dimethylaminoethyl chloride. The products were alkylated with methyl iodide and, in some cases, other alkyl halides to give cationic gemini surfactants. Alkylation of one series with ethyl bromoacetate followed by anion exchange resin catalyzed ester hydrolysis gave zwitterionic gemini surfactants. The members of all series have superior surfactant properties.

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Section: Jocarticlementioning

confidence: 99%

Synthesis of Surfactants Based on Pentaerythritol. I. Cationic and Zwitterionic Gemini Surfactants

et al. 2009

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“…Cinnamates 3a-f were prepared in an easy way applying the widely known HWE reaction [45][46][47] using triethyl phosphonoacetate 1 as the starting material, and commercially available aryl aldehydes 2a-f [4-(diethylamino)benzaldehyde, 4-(diphenylamino)benzaldehyde, terephthaldehyde, 4-(4-morpholinyl)benzaldehyde, 4-acetamidobenzaldehyde, and 3,4,5trimethoxybenzaldehyde] using K 2 CO 3 as base and ethanol as solvent, under microwave irradiation at 140 °C for 20 min. Aer purication either by chromatography column or crystallization, the compounds 3a-f were obtained predominantly as E isomers with 73% to 96% yields (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Green synthesis of ethyl cinnamates under microwave irradiation: photophysical properties, cytotoxicity, and cell bioimaging

Aztatzi-Mendoza,

Porras-Núñez,

Rivas-Galindo

et al. 2024

RSC Adv.

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“… 19 Thus, by combination of the two name reactions some versatile methodologies for the synthesis of arylvinyl-substituted compounds have been developed. 20 On the basis of these observations, we envisioned that quinoline-3-carboxylate upon bearing two active halomethyl functional groups at its 2- and 4-positions might be a feasible building block to undergo the Arbuzov reaction and subsequent HWE olefination reaction process to access structurally novel and intriguing 2,4-bis(( E )-styryl)quinoline-3-carboxylate as shown in Route 2 of Scheme 2 .…”

Section: Resultsmentioning

confidence: 99%

First synthesis of novel 2,4-bis((E)-styryl)quinoline-3-carboxylate derivatives and their antitumor activity

Gao

et al. 2018

RSC Adv.

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A convenient method for the preparation of chiral phosphonoacetamides and their Horner–Wadsworth–Emmons reaction

Cited by 18 publications

References 86 publications

Synthesis of Surfactants Based on Pentaerythritol. I. Cationic and Zwitterionic Gemini Surfactants

Synthesis of Surfactants Based on Pentaerythritol. I. Cationic and Zwitterionic Gemini Surfactants

Green synthesis of ethyl cinnamates under microwave irradiation: photophysical properties, cytotoxicity, and cell bioimaging

First synthesis of novel 2,4-bis((E)-styryl)quinoline-3-carboxylate derivatives and their antitumor activity

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