The selective acetylation of primary alcohols in the presence of secondary alcohols in carbohydrates

Rana, Surjit S.; Barlow, Joseph J.; Matta, Khushi L.

doi:10.1016/s0040-4039(01)92405-0

Cited by 71 publications

(8 citation statements)

References 9 publications

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“…[6][7][8] Also, these compounds play an important role in the synthesis of natural products and poly functional molecules such as nucleosides, carbohydrates, and steroids. [9][10][11] The acylation of alcohols, phenols, thiols and amines is one of the most common and valuable transformations in organic synthesis. 12 The strategy R R X H also provides a convenient and inexpensive route for protecting hydroxyl and amino groups in a multistep synthetic process.…”

Section: Introductionmentioning

confidence: 99%

Untitled

Kazemi

Sanchez-Mendoza

Ghobadi

2019

JMCS

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The hazardous and toxic nature of many solvents, in particular organic solvents that are extensively used in large scale for organic reactions have transformed a serious threat to the environment. Therefore, the design of solvent-free catalytic reaction has received considerable attention during recent times in the field of green synthesis. A solvent-free or solid state reaction may be accomplished using the reactants single or merge them in clays, zeolites, silica, alumina or other substrates. Esters, thioesters and amides are important and valuable compounds in the area of industry, medicine, pharmaceutical and heterocyclic chemistry. In this paper, various solventfree systems to synthesize esters, thioesters and amides via the acylation of alcohols, phenols, thiols and amines are described. In this review we summarized the activities presented mainly the recent years. reusable catalyst for the synthesis of esters and amides under solvent-free conditions (Scheme 5). 50 Scheme 3. Solvent-free diacylation of aldehydes using ATPB. Scheme 4. Solvent-free acylation of alcohols, thiols and amines catalyzed by ZrOCl 2 .8H 2 O.An convenient method with the same reagents and in the presence of lithium bis(perfluoroalkylsulfonyl)-imide (LiPFS-I) has also been developed (Scheme 24). 76 Scheme 24. Solvent-free acylation of alcohols using LiPFSI.Another practical and highly efficient strategy was also described with SiO 2 -Co(acac) 2 and SiO 2 -Cu(acac) 2 under solvent-free conditions (Scheme 25). 77 The acylation of alcohols, phenols and amines with acetyl chloride was carried out in less than 60 min at 50 0 C. The esterification of alcohols and amines was performed respectively with SiO 2 -Cu(acac) 2 and SiO 2 -Co(acac) 2. Scheme 25. Solvent-free acylation of alcohols and amines using SiO 2 -Co(acac) 2 and SiO 2 -Cu(acac) 2 . 7 M. Kazemi et al Journal of Medicinal and Chemical Sciences Review J. Med. Chem. Sci. 2019, 1, 1-8 http://jmchemsci.com Scheme 30. Solvent-free diacylation of aldehydes catalyzed by n-Sulfonic acid poly4-vinylpyridinum) hydrogen sulfate.

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Section: Introductionmentioning

confidence: 99%

Untitled

Kazemi

Sanchez-Mendoza

Ghobadi

2019

JMCS

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“…In addition, 4-(dimethylamino)pyridine, 4-pyrrolidinopyridine 3 . Tetramethylethylenediamine 4 , tertiary phosphines 5 , carbon tetrabromide in ethyl acetate 6 , p-toluenesulfonic acid 7 , zinc chloride 8 , iodine 9 , sulfamic acid 10 , magnesium bromide 11 , cobalt chloride 12 , tantalum chloride 13 , La(OPr-i)3 14 , silica gel-supported sodium hydrogen sulfate 15 , montmorillonite K-10 and KSF 16 , alumina 17 , yttria zirconia with acetic acid 18 , Ac2O-pyridine/basic alumina under microwave irradiation 19 , KF-Al2O3 with Ac2O/AcCl 20 , vanadyl(V) acetate 21 , distannoxane 22 , zeolite HSZ-360 23 , Pseudo-monas cepacia PS lipase adsorbed on Celite 24 , and twisted amides 25 have also been applied for the acetylation of alcohols and phenols. Another important development has been the introduction of trifluorme-thanesulfonate derivatives, such as TMSOTf 26 , Yb-(OTf)3 27 , Cu(OTf)2 28 , Sc(OTf)3 29 , In(OTf)3 30 , Bi(OTf)3 31 , cerium(III) 32 and (IV) 33 salts as efficient catalysts in acetylation with acetic acid, or anhydride or acetyl chloride.…”

Section: Introductionmentioning

confidence: 99%

Microwave-Assisted Acetylation of Phenols without Catalyst Under Solvent Free Condition

Zhang¹,

Li²,

Zhu³

et al. 2014

Asian J. Chem.

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“…An esterification is a key and fundamental step to protect hydroxyl group during functional transformation in various organic synthesis [1][2][3]. However, protection and deprotection of hydroxyl functional group of alcohols and phenols being not only prime importance in pharmaceutical industries but also in the polymers, cosmetics, perfumes, plasticizers to achieve excellent yield to potential targeted synthetic compounds.…”

Section: Introductionmentioning

confidence: 99%