Synthesis and spectroscopic properties of long‐chain aza, aziridine and azetidine fatty esters

Jie, Marcel S. F. Lie Ken; Syed‐Rahmatullah, M. S. K.

doi:10.1007/bf02636068

Cited by 19 publications

(14 citation statements)

References 18 publications

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“…In addition, 30% of the substrate could be recovered as a regio-and diastereomeric mixture in almost the same composition. No competing formation of an azetidine [4] with inclusion of the hydroxy function at C-12 and the azido group at C-10 was observed. The change in the diastereomeric ratio of the resulting aziridine 12 (2.5:1) compared to the epoxide 7 (1.2:1) could not be explained satisfactory.…”

Section: Synthesis Of Azido Alcohols and Aziridinesmentioning

confidence: 78%

“…4.04 g, 20 mmol) was added under argon, the reaction temperature not being allowed to rise above 30°C. The reaction mixture was heated at reflux for a further 30 min until TLC showed complete reaction of the starting compound.…”

Section: Methyl 1011-epiminoundecanoate (15)mentioning

confidence: 99%

“…Lie Ken Jie [4] reported on the transformation of methyl cis-9, 10-epoxyoctadecanoate (1) into the corresponding aziridine (3) (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

“…We have also continued our previous investigations into bis-and tris(aziridines) derived from methyl linoleate Scheme 1. Synthesis of methyl cis-9, 10-epiminooctadecanoate (3), starting from methyl cis-9, 10-epoxyoctadecanoate (1), via azido alcohol 2 [4] Figure 1. Bis(aziridine) 4, based on methyl linoleate, and tris(aziridine) 5, based on methyl linolate [1] and methyl linolate [1] and are now able to report on their remarkable biological activities.…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Fat‐Derived Aziridines and Their N‐Substituted Derivatives: Biologically Active Compounds Based on Renewable Raw Materials

Fürmeier

Metzger

2003

Eur J Org Chem

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The first successful preparation of the aziridines methyl (9Z,12S,13R)‐12,13‐epimino‐9‐octadecenoate (10), derived from vernolic acid, and methyl (9R,10S,12R)‐9,10‐epimino‐12‐hydroxyoctadecanoate (12a) and methyl (9S,10R,12R)‐9,10‐epimino‐12‐hydroxyoctadecanoate (12b), both derived from ricinoleic acid, is reported. These are the first examples of enantiomerically pure fat‐derived aziridines. Treatment of the corresponding epoxides with sodium azide and ammonium chloride in ethanol in the presence of water yielded the new azido hydroxy compounds, which could be treated in an improved way with polymer‐bound triphenylphosphane to afford the aziridines in good yields. The intermediate azido hydroxy compounds could easily be reduced and so offer access to a variety of interesting β‐amino alcohols 17−21. The synthesis of various N‐substituted aziridine derivatives 22−29 by treatment of methyl cis‐9,10‐epiminooctadecanoate (3) with phenyl isocyanate and isothiocyanate, acetyl chloride, alkyl and aryl chloroformates and acrylonitrile is described. Finally, the fat‐derived 2,5‐dialkyl‐substituted pyrrole methyl 9‐(5‐pentyl‐1H‐pyrrol‐2‐yl)nonanoate (9) was obtained. The previously reported bis(aziridine) methyl cis‐9,10;cis‐12,13‐diepiminooctadecanoate, derived from linoleic acid, and tris(aziridine) methyl cis‐9,10;cis‐12,13;cis‐15,16‐triepiminooctadecanoate, derived from linolenic acid,1 have been subjected to different biological tests and showed cytotoxic and antimicrobial activity as well as remarkable antitumour‐promoting and good neuroprotective effects. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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Section: Synthesis Of Azido Alcohols and Aziridinesmentioning

confidence: 78%

Section: Methyl 1011-epiminoundecanoate (15)mentioning

confidence: 99%

“…Lie Ken Jie [4] reported on the transformation of methyl cis-9, 10-epoxyoctadecanoate (1) into the corresponding aziridine (3) (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Fat‐Derived Aziridines and Their N‐Substituted Derivatives: Biologically Active Compounds Based on Renewable Raw Materials

Fürmeier

Metzger

2003

Eur J Org Chem

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“…Besides ESBO, epoxidized methyl oleate has been transformed to aziridine [54] and episulfide [55] (Scheme 11). These compounds are interesting intermediates in the synthesis of heterocyclic and highly functionalized substances [42].…”

Section: Soybean Oil Epoxized Soybean Oil (Esbo)mentioning

confidence: 99%

Biodegradable polymers from monomers based on vegetable oils

Sun¹,

Kuckling²

2017

Biodegradable Polymers: Recent Developments and New Perspectives

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New Type of Skipped Oligoaziridines: Synthesis of New Fatty AcidDerivatives Containing Aziridine Functions

Metzger¹,

Fürmeier

1999

Eur. J. Org. Chem.

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The first successful preparation of the aziridines methyl cis‐9,10;cis‐12,13‐diepiminooctadecanoate (3) derived from linoleic acid, and methyl cis‐9,10;cis‐12,13;cis‐15,16‐triepiminooctadecanoate (6) derived from linolenic acid, is reported. Remarkably, the bis‐ and trisaziridine were obtained in a reaction sequence that consists of only two steps, using technically pure methyl esters of epoxidized sunflower and linseed oil. The conversion of methyl 9,10;12,13‐diepoxyoctadecanoate (1), with sodium azide and ammonium chloride in ethanol in the presence of water, yielded the new diazidodihydroxy compound methyl 9(10),12(13)‐diazido‐10(9),13(12)‐dihydroxyoctadecanoate (2) in the first step. 2 was obtained as a regioisomeric mixture. The reaction of 2 with triphenylphosphane led to the bisaziridine 3. The analogous conversion of methyl 9,10;12,13;15,16‐triepoxyoctadecanoate (4), via the new triazidotrihydroxy compound methyl 9(10),12(13),15(16)‐triazido‐10(9),13(12),16(15)‐trihydroxyoctadecanoate (5), afforded trisaziridine 6.

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Synthesis and spectroscopic properties of long‐chain aza, aziridine and azetidine fatty esters

Cited by 19 publications

References 18 publications

Fat‐Derived Aziridines and Their N‐Substituted Derivatives: Biologically Active Compounds Based on Renewable Raw Materials

Fat‐Derived Aziridines and Their N‐Substituted Derivatives: Biologically Active Compounds Based on Renewable Raw Materials

Biodegradable polymers from monomers based on vegetable oils

New Type of Skipped Oligoaziridines: Synthesis of New Fatty AcidDerivatives Containing Aziridine Functions

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