New N-acylamino acids and derivatives from renewable fatty acids: gelation of hydrocarbons and thermal properties

Duarte, Rodrigo da Costa; Ongaratto, Renata; Piovesan, Luciana A.; Lima, Vânia Rodrigues de; Soldi, Valdir; Merlo, Aloir A.; D’Oca, Marcelo Gonçalves Montes

doi:10.1016/j.tetlet.2012.03.015

Cited by 29 publications

(15 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Reactions of FAME with a 3 mol equivalent of hydrazine monohydrochloridrate and a 3 mol equivalent of sodium hydroxide as bases in the presence of methanol under reflux for 48 h yielded pure samples of fatty N-acyl hydrazines 3a-c (Table 1, entries [11][12][13]. In this case, the use of sodium methoxide did not lead to the desired products, regardless of the molar ratio or reaction time used (entries [14][15][16][17][18][19]. The progress of all reactions was monitored by silica gel TLC.…”

Section: Resultsmentioning

confidence: 99%

“…These molecules are structurally simple, low in cost and because of the inclusion of fatty chains have increased lipophilicity. [14][15][16] This paper describes a synthetic method for preparing new fatty N-acyl trihalomethylated pyrazoline derivatives from C16:0, 18:0 and 18:1 fatty acid families. It aimed at the study of fatty molecules with biological potential, bearing in mind the synthesis of pyrazole compounds from 4-alkoxy-1,1,1-trihalo-3-alken-2-ones in close connection with this research.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Regiospecific synthesis of new fatty N-acyl trihalomethylated pyrazoline derivatives from fatty acid methyl esters (FAMEs)

Beck¹,

Santos²,

Kuhn³

et al. 2012

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

Uma série de novas pirazolinas N-acil trialometiladas derivadas de ésteres metílicos de ácidos graxos foi sintetizada por reação de ciclocondensação entre hidrazidas graxas e 4-alcóxi-1,1,1-trialometil-3-alquen-2-onas. Ciclizações eficientes e regioespecíficas catalisadas por BF 3 ·MeOH levaram aos produtos desejados em rendimentos de bons a excelentes e alto grau de pureza.A series of new fatty N-acyl trihalomethylated pyrazoline derivatives from fatty acid methyl esters was synthesized by the cyclocondensation of respective fatty hydrazides with 4-alkoxy-1,1,1-trialomethyl-3-alquen-2-ones. Efficient and regiospecific cyclizations catalyzed by BF 3 ·MeOH gave the desired products in good to excellent yields and at high purity.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Regiospecific synthesis of new fatty N-acyl trihalomethylated pyrazoline derivatives from fatty acid methyl esters (FAMEs)

Beck¹,

Santos²,

Kuhn³

et al. 2012

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

show abstract

“…LMWGs are representative supramolecular gelators. LMWGs can self-assemble into fibrous or sheet-like structures, because of their non-covalent hydrogen bonding, - stacking, hydrophobic and / or van der Waals interactions [24,26,[32][33][34]. Noncovalent interactions between gelator molecules create a three-dimensional network, and provide flexibility to the gel network.…”

Section: Introductionmentioning

confidence: 99%

Palmitoylated amino acids as low-molecular-weight gelators for ionic liquids

et al. 2017

View full text Add to dashboard Cite

“…In a continuation of our studies to synthesize compounds from renewable resources [37][38][39][40], we describe here the synthesis of fatty acetoacetates 2a-l derivatives from renewable saturated, unsaturated, polyunsaturated and ricinoleic fatty acids using the transesterification reaction under sulfamic acid (NH 2 SO 3 H) catalysis and solvent-free conditions using long chain alcohols (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Fatty Acetoacetates Under Microwave Irradiation Catalysed by Sulfamic Acid in a Solvent‐Free System

Weber

Batista

Gonçalves

et al. 2016

J Americ Oil Chem Soc

View full text Add to dashboard Cite

of polymers, drugs and biologically active compounds [1][2][3]. They have also been studied as biofuel additives [4].Using acetoacetates as the building blocks in multicomponent reactions (MCR) [5] yields several different structures based on the dihydropyridinone (DHPM) or dihydropyridine (DHP) skeleton, which creates an extensive library of compounds with various biological activities [6-10]. MCR have been recognized for their high convergence, atomic economy and operational simplicity and are emphasized as important tools to synthesize high-molecular-complexity compounds in accordance with green chemistry principles [2,11].The transesterification reaction to synthesize acetoacetates is a notably useful tool in organic synthesis, and various methods have been reported to affect the transesterification of methyl or tert-butyl acetoacetates. The uncatalyzed transesterification of acetoacetates requires the use of either an excess of ketoester or a longer reaction time and a high boiling alcohols or solvents limiting their usage [12].According to the literature, the transesterification process to synthesize β-ketoesters under solvent-free conditions without catalysis results in high yields when excess alcohol is used at a high temperature [13]. In addition, the rate of transesterification of acetoacetates is significantly affected by steric factors; thus, tertiary alcohols are less active. Primary, secondary, and tertiary alcohols have been tested in the presence of molecular sieves, which results in good acetoacetate yields [12]. The catalysts in the transesterification reaction vary and include new silica-based hybrid materials, triethylamine, boric acid, and triphenylphosphine [14][15][16][17].However, the development of a new method that enables transesterification in milder conditions should heighten the synthetic potential of the reaction. Considering the importance of acetoacetates, cleaner methodologies have been studied for their synthesis; solvent-free conditions [18] and replacement of catalysts [13] render the protocol to obtain Abstract The 1,3-dicarbonyl compounds are important building blocks to obtain products with various biological activities and technological applications. In this work, we used a simple transesterification method to develop fatty acetoacetates in a solvent-free medium using a green catalyst, sulfamic acid (NH 2 SO 3 H), under microwave irradiation. The experimental results demonstrate good yields in a short reaction time (13 min), which makes this method an efficient approach to synthesize fatty acetoacetates from a wide range of saturated, unsaturated, and polyunsaturated long chain fatty alcohols, and ricinoleic derivatives. Experiments of recycling of the catalyst were performed and no decrease in catalytic activity of sulfamic acid was observed.

show abstract

New N-acylamino acids and derivatives from renewable fatty acids: gelation of hydrocarbons and thermal properties

Cited by 29 publications

References 15 publications

Regiospecific synthesis of new fatty N-acyl trihalomethylated pyrazoline derivatives from fatty acid methyl esters (FAMEs)

Regiospecific synthesis of new fatty N-acyl trihalomethylated pyrazoline derivatives from fatty acid methyl esters (FAMEs)

Palmitoylated amino acids as low-molecular-weight gelators for ionic liquids

Synthesis of Fatty Acetoacetates Under Microwave Irradiation Catalysed by Sulfamic Acid in a Solvent‐Free System

Contact Info

Product

Resources

About