Synthesis of benzoyl and dodecanoyl derivatives from protected carbohydrates under focused microwave irradiation

Limousin, Corinne; Cléophax, J.; Loupy, André; Petit, Alain

doi:10.1016/s0040-4020(98)00834-5

Cited by 40 publications

(20 citation statements)

References 39 publications

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“…23,24 Namely, microwave-assisted phase transfer catalyzed (Bu4NBr) reaction in basic medium (K2CO3) of methyl salicylate with 2-amino-2-(hydroxymethyl)propane-1,3-diol 1a, at the mole ratio methyl salicylate/alcohol 1a 2:1 during 15 min, yielded the oxazoline derivative 2a. However, when the mole ratio metyl salicylate/alcohol 1a was 6:1 and the reaction time extended to 30 min, then, in addition to compound 2a, the product was also salicyloyloxymethyl derivative 3 ( Table 1, Table 2).…”

Section: Chemistrymentioning

confidence: 99%

“…The obtained crude mixture was separated on silica gel column (toluene, then toluene -EtOAc 4:1). The resulting products were 4c (mp 117 ºC after recrystallization from chloroform, mp 117 ºC 23 ), 5c (mp 97 ºC after recrystallization from CH2Cl2 -n-hexane, lit 23 mp 98 ºC), 5d (mp 184 ºC after recrystallization from 95% ethanol, mp 185 ºC 24 ), and 8c (mp 183 ºC after recrystallization from 95% ethanol, mp 184-185 ºC 26 ) in yields given in Table 3.…”

Section: Cytotoxicitymentioning

confidence: 99%

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Synthesis and biological evaluation of some new 2-oxazoline and salicylic acid derivatives

Djurendić¹,

Vujašković²,

Sakač³

et al. 2010

Arkivoc

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Starting from methyl salicylate and 2-amino-2-(hydroxymethyl)propane-1,3-diol 1a, or 2-amino-2-methylpropane-1-ol 1b, the 2-oxazoline derivatives 2a, 2b or 3, as well as mono-4a and 4b and bis-5a and 5b derivatives of salicylic acid were synthesized. Reactions were performed by microwave irradiation in the presence of tetrabutylammonium bromide or metallic sodium as catalyst, as well as by conventional heating. Microwave-induced reaction of some diols, diamines and amino alcohols with methyl salicylate gave mono-and/or bis-derivatives of salicylic acid 4c, 5c, 5d, 6c, 8c, 7a, 7b, 8a and 8b. The mono-and bis-salicyloyl derivatives 4c, 5c and 5d were transformed to the corresponding phenyl-azo derivatives 9, 10c and 10d. The structure of compound 3 was proved by the X-ray analysis and the R-configuration on its stereocenter was confirmed. The antioxidant and cytotoxic activities of the synthesized derivatives were evaluated in a series of in vitro tests. Compounds 5d, 8b and 8c exhibited very strong activity against hydroxyl radical. Six 4c, 5d, 8a-c, 10c of 16 tested compounds inhibited growth of MDA-MB-231 cells at a nanomolar concentration. Compounds 8c and 10c showed high cytotoxicity against MCF7 cells, whereas compounds 4c, 5d, 8a-c and 10d showed high activity against K562 cells.

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Section: Chemistrymentioning

confidence: 99%

Section: Cytotoxicitymentioning

confidence: 99%

Synthesis and biological evaluation of some new 2-oxazoline and salicylic acid derivatives

Djurendić¹,

Vujašković²,

Sakač³

et al. 2010

Arkivoc

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“…The role of DMF can be explained as an energy transfer agent and homogenizer to increase the reaction temperature. 10,11 No formation of any detectable by-products were observed, which implies a drying effect. This method has the advantage of complete elimination of solvent for adsorption of reactant and desorption of product from the recyclable solid support.…”

Section: Resultsmentioning

confidence: 92%

“…The compounds 6b-c were prepared by following the same procedure. 11,H: 4.39,N: 18.08,Found C: 65.24,H: 4.48, N: 18.15%.…”

Section: 1'22'-tetrahydro-4'-amino-7'-(4-fluorophenyl)-spiro[3h-imentioning

confidence: 97%

Facile one pot microwave enhanced multistep synthesis of novel biologically important scaffold spiro[indole-pyridopyrimidines]

Dandia¹,

Arya²,

Khaturia³

2005

Arkivoc

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A rapid and efficient one pot method for the preparation of novel spiro [indole-pyrido[2,3-d]pyrimidines] by the reaction of 'insitu' generated spiro [indole-dihydropyridine] and urea / CS 2 using basic alumina as solid support/ or few drops of DMF as homogenizer under microwave irradiation is reported. Excellent yields (85-89%) and higher purity are obtained in mw enhanced one pot synthesis as compared to conventional procedure which required multistep processes using organic solvents and tedious workups.

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“…5). For carbohydrates not stable in acid conditions, such as 4,6-O-benzylidene--D-glucopyranose, benzoylation can be achieved via transesterification with methyl benzoate using a week and non nucleophilic base promoter like potassium carbonate and a phase transfer agent (Limousin, 1998). MW permits again a tuning of the regioselectivity.…”

Section: Hydroxyls Protections/deprotectionsmentioning

confidence: 99%

Conversion of Carbohydrates Under Microwave Heating

Richel¹,

Paquot²

2012

Carbohydrates - Comprehensive Studies on Glycobiology and Glycotechnology

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Synthesis of benzoyl and dodecanoyl derivatives from protected carbohydrates under focused microwave irradiation

Cited by 40 publications

References 39 publications

Synthesis and biological evaluation of some new 2-oxazoline and salicylic acid derivatives

Synthesis and biological evaluation of some new 2-oxazoline and salicylic acid derivatives

Facile one pot microwave enhanced multistep synthesis of novel biologically important scaffold spiro[indole-pyridopyrimidines]

Conversion of Carbohydrates Under Microwave Heating

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