Solvent-free direct regioselective ring opening of epoxides with imidazoles

Torregrosa, Rosario; Pastor, Isidro M.; Yus, Miguel

doi:10.1016/j.tet.2006.10.055

Cited by 57 publications

(49 citation statements)

References 20 publications

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“…These enantiomers can be used as chiral synthons for new drugs, pesticides or task-specific ionic liquids. The 1-(β-hydroxypropyl)-imidazole (±)- 3a and -triazole (±)- 3b used in this study were prepared as racemic mixtures according to the method described by Yus and co-workers [46] (Scheme 1). Next, these compounds were used as a new type of substrate in lipase-catalyzed transesterification, yielding both enantiomers with good optical purity.…”

Section: Resultsmentioning

confidence: 99%

Chemoenzymatic synthesis and biological evaluation of enantiomerically enriched 1-(β-hydroxypropyl)imidazolium- and triazolium-based ionic liquids

Borowiecki¹,

Milner-Krawczyk²,

Plenkiewicz³

2013

Beilstein J. Org. Chem.

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SummaryRacemic 1-(β-hydroxypropyl)azoles were prepared by solvent-free direct regioselective ring opening of 1,2-propylene oxide with imidazole or 1,2,4-triazole. Lipase-catalyzed transesterification of alcohols with vinyl acetate resulted in kinetic enantiomers resolution. Separated (S)-enantiomers of (+)-1-(1H-imidazol-1-yl)propan-2-ol and (+)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol were quaternized with alkyl bromides or iodides, yielding novel optically active ionic liquids. Racemic salts were tested against a wide range of microorganisms.

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Section: Resultsmentioning

confidence: 99%

Chemoenzymatic synthesis and biological evaluation of enantiomerically enriched 1-(β-hydroxypropyl)imidazolium- and triazolium-based ionic liquids

Borowiecki¹,

Milner-Krawczyk²,

Plenkiewicz³

2013

Beilstein J. Org. Chem.

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“…The search for novel surfactants with higher efficiency and effectiveness gave birth to the concept of Gemini surfactants. These compounds are also applicable in the solubilization of dyes and pigments in the textile industry [10][11][12][13], gene therapy [14][15][16][17], the synthesis of highly mesoporous materials [18,19], etc. Gemini surfactants are a new generation of surfactants composed of two monomeric surfactant molecules chemically bonded together by a spacer at or near their head groups.…”

Section: Introductionmentioning

confidence: 99%

Gemini Pyridinium Surfactants: Synthesis and Their Surface Active Properties

Patial

Shaheen

Ahmad

2014

J Surfact & Detergents

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New pyridinium Gemini surfactants have been synthesized by esterification of renewable fatty acids with halogenated alcohols furnishing respective esters (2‐chloroethyl hexadecanoate, 2‐chloroethyl tetradecanoate, 2‐chloroethyl dodecanoate, 2‐bromoethyl hexadecanoate, 2‐bromoethyl tetradecanoate and 2‐bromoethyl dodecanoate) followed by their subsequent treatment with 4,4′‐trimethylenedipyridine resulting into the formation of title Gemini surfactants: (4,4′‐(propane‐1,3‐diyl)bis(1‐(2‐(hexadecanoyl oxy) ethyl) dipyridinium chloride(7), (4,4′‐(propane‐1,3‐diyl)bis(1‐(2‐(tetradecanoyl oxy) ethyl) dipyridinium chloride (8), 4,4′‐(propane‐1,3‐diyl)bis(1‐(2‐(dodecanoyl oxy) ethyl) dipyridinium chloride (9), (4,4′‐(propane‐1,3‐diyl)bis(1‐(2‐(hexadecanoyl oxy) ethyl) dipyridinium bromide (10), (4,4′‐(propane‐1,3‐diyl)bis(1‐(2‐(tetradecanoyl oxy) ethyl) dipyridinium bromide (11), 4,4′‐(propane‐1,3‐diyl)bis(1‐(2‐(dodecanoyl oxy) ethyl) dipyridinium bromide (12). Their identifications are based on IR, 1H‐, 13C‐NMR, DEPT, COSY and mass spectral studies. Their surface active properties are also evaluated on the basis of surface tension and conductivity measurements and thermal stability of these long chain cationics Gemini surfactants have been measured by thermal gravimetric analysis under nitrogen atmosphere.

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“…[3] Imidazolium salts, which are usually employed in the formation of NHC ligands, can be prepared with a variety of functionalities. [9][10][11] Recently, we have described the preparation of well-defined NHC-Os complexes [10] and bis(NHC)-Pd complex [11] 1 by direct metalation from the corresponding imidazolium salts. [9][10][11] Recently, we have described the preparation of well-defined NHC-Os complexes [10] and bis(NHC)-Pd complex [11] 1 by direct metalation from the corresponding imidazolium salts.…”

Section: Introductionmentioning

confidence: 99%

Heck–Matsuda Reactions Catalyzed by a Hydroxyalkyl‐Functionalized NHC and Palladium Acetate

2012

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The functionalized NHC obtained from salt 2 is a good ligand for palladium in the Heck–Matsuda reaction of arenediazonium salts and different alkenes. The reaction is performed with low catalyst loading (0.5–1 mol‐% of Pd) and in the absence of a base for acrylates. The protocol is also useful for the preparation of cinnamide derivatives. Compound U‐77863 has been prepared successfully in good isolated yield. Cyclohexene was found to be an appropriate substrate for the reaction, giving the corresponding 1‐arylcyclohexene as a single regioisomer under the studied reaction conditions. The optimal parameters of the reaction were studied by employing a design of experiments approach. Thus, the use of a small set of reactions allows the trends of the different factors to be studied. This study revealed that the best catalytic system is formed by combination of Pd(OAc)2 and salt 2 in a 1:2 ratio. This catalytic system produces better results without the use of a base.

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Solvent-free direct regioselective ring opening of epoxides with imidazoles

Cited by 57 publications

References 20 publications

Chemoenzymatic synthesis and biological evaluation of enantiomerically enriched 1-(β-hydroxypropyl)imidazolium- and triazolium-based ionic liquids

Chemoenzymatic synthesis and biological evaluation of enantiomerically enriched 1-(β-hydroxypropyl)imidazolium- and triazolium-based ionic liquids

Gemini Pyridinium Surfactants: Synthesis and Their Surface Active Properties

Heck–Matsuda Reactions Catalyzed by a Hydroxyalkyl‐Functionalized NHC and Palladium Acetate

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