Potential Toxicological Concerns Associated with Carboxylic Acid Chlorination and Other Reactions

Levin, Daniel

doi:10.1021/op970206t

Cited by 45 publications

(28 citation statements)

References 2 publications

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“…It is important to mention that although many procedures for the formation of amides are known in the literature, the most widely used employs carboxylic acid chlorides as the electrophiles which react with the amino group in the presence of an acid scavenger 13 . Despite its wide scope, this protocol suffers from several drawbacks: most notable are the limited stability of many acid chlorides and the need for hazardous reagents for their preparation (e.g., thionyl chloride) 14 . Therefore, in this study N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide (EDC) 15 .54 ppm for methylenes bound to both amide and ester groups; at 3.38 and 3.74 ppm for methylenes bound to imino and amino groups; at 3.80 and 3.90 ppm for methoxy groups were found.…”

Section: Resultsmentioning

confidence: 99%

A Facile Synthesis of Two Brucine-Steroid Derivatives

Figueroa‐Valverde

Cedillo²,

Elodia

et al. 2013

Asian J. Chem.

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There are studies which show that several derivatives of brucine have been developed for its use in different biological and analytical methods 1-4. For example, a report shows the synthesis of N-chloromethylbrucine chloride by the reaction of brucine with dichloromethane 5. Other studies have shown the preparation of a brucine derivative (brucidine) by electrolytic reduction of brucine 6. In addition, there are reports of the synthesis of N-(5-carboxypentyl)brucinium bromide via N-alkylation of brucine with 6-bromohexanoic acid 7. Other experimental data showed the preparation of compounds brucinium hydrogen (S)-malate pentahydrate and anhydrous brucinium hydrogen (2R,3R)-tartrate by the reaction between brucine and D-L-malic acid or L-tartaric acid in ethanol:water 8. Additionally, the porphyrin-brucine conjugates was synthetized by the N-alkylation of brucine with alkylbromotetraphenylporphyrin derivatives 9. Recently, a brucine derivative (N 1-(2,3-dimethoxy strychnidin-10-yliden)-ethane-1,2-diamine) was synthetized by the reaction of brucine and ethylenediamine using boric acid as catalyst. Also other brucine derivative (11-[(2-aminoethylamino)-methyl]-2,3-dimethoxystrychnidin-10-ona) was prepared by the reaction of brucine with ethylenediamine in presence of formaldehyde 10. Additionally, other study showed the synthesis of a brucine-dihydropirymidine derivative using the multi-component system (brucine, benzaldehyde and

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Section: Resultsmentioning

confidence: 99%

A Facile Synthesis of Two Brucine-Steroid Derivatives

Figueroa‐Valverde

Cedillo²,

Elodia

et al. 2013

Asian J. Chem.

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show abstract

“…It is important to mention that although many procedures for the formation of amides are known in the literature, the most widely used employs carboxylic acid chlorides as the electrophiles which react with the amino group in the presence of an acid scavenger 18 . Despite its wide scope, this protocol suffers from several drawbacks: most notable are the limited stability of many acid chlorides and the need for hazardous reagents for their preparation (e.g., thionyl chloride) 19 . Therefore, in this study N-(3-Dimethylaminopropyl)-N'-ethylcarbodiimide (EDC) 20 18 and 62.36 ppm for carbons involved in the spacer arm between both imino and amide groups; at 162.50-162.52 ppm for carbon bound to both imino and aromatic ring; at 163.38 ppm for amide group were found.…”

Section: Resultsmentioning

confidence: 99%

Design and Synthesis of an Aromatic-steroid Derivative

Figueroa‐Valverde

Cedillo²,

Elodia

et al. 2013

Orientjchem.

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“…Despite its wide scope, the former protocol suffers from several drawbacks. The most notable are the limited stability of many acid chlorides and the need for hazardous reagents for their preparation (thionyl chloride) 17 . Nevertheless, there are reports which indicate that 1-ethyl-3-(3-dimethyl-aminopropyl) carbodiimide hydrochloride catalyzed amidation reaction with high yielding 18 .…”

Section: Resultsmentioning

confidence: 99%

Design and Synthesis of Two Brucine Derivatives

Figueroa‐Valverde¹,

Díaz-Cedillo²,

García-Cervera³

et al. 2013

Asian J. Chem.

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In this study, two brucine derivative were synthetized; in first stage, the compound 1-{phenyl-[2-(2,3-dimethoxystrychnidin-10yldeneamino)-ethylamino]-methyl}-naphtalen-2-ol (4) was development by the reaction of β-naphthol, N 1 -(2,3-dimethoxystrychnidin-10-yliden)-ethane-1,2-diamine and benzaldehyde in ethanol. Also 4 was prepared by the reaction of brucine with 1-[(2-amino-ethylamino)phenyl-methyl]-naphthalen-2-ol using as catalyst boric acid. In the second stage, the compound 4-hydroxy-N-[2-(2,3-dimethoxystrychnidin-10-ylideneamino)-ethyl]benzamide (8) was synthetized by the reaction of 4-hydroxybenzoic acid with N 1 -(2,3-dimethoxystrychnidin-10-yliden)-ethane-1,2-diamine using a carbodiimide derivative as catalyst. Finally, in other experiment the compound 8 was also prepared by the reaction of brucine with N-(2-aminoethyl)-4-hydroxybenzamide in presence of a carbodiimide derivative. The structure of all compounds obtained was confirmed by elemental analysis and spectroscopic methods.

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Potential Toxicological Concerns Associated with Carboxylic Acid Chlorination and Other Reactions

Cited by 45 publications

References 2 publications

A Facile Synthesis of Two Brucine-Steroid Derivatives

A Facile Synthesis of Two Brucine-Steroid Derivatives

Design and Synthesis of an Aromatic-steroid Derivative

Design and Synthesis of Two Brucine Derivatives

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