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The stereoselective formation of β-lactams with acyl ketenes generated from 5-acyl-Meldrum's acids
PublikacjaAcyl ketenes formed during thermal decompositions of 5-acyl-2,2-dimethyl-1,3-dioxa-4,6-diones undergo stereoselective [2+2] cycloaddition to chiral aldimines. We report the first example of optically active 3-acyl-β-lactams formation from Meldrum’s acid derivatives.
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New thiourea organocatalysts and their application for the synthesis of 5-(1H-indol-3-yl)methyl-2,2-dimethyl-1,3-dioxane-4,6-diones a source of chiral 3-indoylmethyl ketenes
PublikacjaThe stereoselective properties of modified thiourea organocatalysts were tested in the Friedel–Crafts alkylation of indole with 5-arylidene-2,2-dimethyl-1,3-dioxane-4,6-diones, which produces chiral 5-((1H-indol-3-yl)(aryl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-diones. Based on a tentative reaction mechanism for ((S)-N-benzyl-2-(3-(3,5-bis (trifluoromethyl)phenyl)thioureido)-N,3,3-trimethylbutanamide organocatalysts, modifications...
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One-Step Synthesis of b-Lactams with Retro-Amide Side Chain
PublikacjaAbstract: A one pot synthesis for preparation of 1,4-disubstituted-2-oxo-azetidine-3-carboxylic acid amides was developed. 5-(α-N-substituted-amino-α'-hydroxy)methylene Meldrum's acids act as a source of ketenes that react with aldimines in boiling toluene to give b-lactams with retro-amid side chain.
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One-step formation of n-alkenyl-malonamides and n-alkenyl-thiomalonamides from carbamoyl meldrum's acids.
PublikacjaA one-pot synthesis for the preparation of N-alkenyl-malonamides and N-alkenyl-thiomalonamides was developed. 5-[Hydroxy/mercapto(aryl/alkylamino)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione act as a source of ketenes that react with the tautomeric form of alkyl-(2-phenyl-propylidene)-amines. A possible [2+2] or [4+2] cycloaddition product of ketene to imines was not observed.
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Thermal Decomposition of Carbamoyl Meldrum’s Acids: A Starting Point for the Preparation of 1,3-Oxazine Derivatives
PublikacjaThe ability to undergo [4 + 2] versus [2 + 2] cycloaddition was under investigation for ketenes thermally generated from carbamoyl Meldrum’s acid. Usually, 1,3-oxazino-5-carbamoylo-4,6-diones are formed when carbamoyl Meldrum’s acid reacts with imine. However, in some cases, a reaction takes an unexpected course, leading to the formation of tetraponerines alkaloids derivatives or cyclic iminoethers.
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Synthesis of malonylenamides and thiomalonylenamides
Publikacja5-[Hydroksyl(aryl(amino))methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione is convenient source of ketenes which can be trapped with various nucleophiles like alcohols, thiols and amines. In reaction between in situ generated ketene and enolizable imines we can easily obtain corresponding malonylenamides. This facile method can be used to obtain thiomalonylenamides using 5-[sulfhydrylo(alkyl(amino))methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione...
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Easy formation of acyl-Meldrum's acid anhydride
PublikacjaAcyl Meldrum's acid are usually a good source of ketenes upon definite thermal composition. However we treated acyl-Meldrum's acid with the Lewis acid and we observed formation of 5[[(2,2-dimethyl-4,6-dioxo-1,3-dioxan 5 ylidene)(acyl/arylamino)mathoxy](acyl/arylamino)methylene]-2,2dimethyl-1,3-dioxane-4,6 dione which means acyl-Meldrum's acid anhydride. The chemical properities of acyl-Meldrum's acid anhydride were explored.
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A new approach to the stereoselective synthesis of trans-3-carbamoyl-b-lactam moieties†
PublikacjaOne-pot synthesis of optically active 1,4-disubstituted-3-carbamoyl-azetidinones from 5-[(N-arylamino)- (hydroxyl)methylene]-2,2-dimethyl-1,3-dioxa-4,6-diones and chiral aldimines is achieved via thermal generation of carbamoyl ketenes and subsequent [2+2] cycloaddition. Three possible chiral induction approaches were tested and (R)-(+)-1-phenylethylamine was confirmed as the best chiral auxiliary. Among the four possible diastereoisomers,...
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Preparation of Pseudopeptides Building Blocks with Retro-Thioamide Bond Mediated via Thiocarbamoyl Meldrum's Acid
PublikacjaAn easy and efficient synthesis of pseudo tripeptide containing a thiomalonamide moiety was developed. Isothiocyanate derivatives of amino acids react smoothly with 2,2-dimethyl-1,3-dioxane-4,6-dione yielding new thiocarbamoyl Meldrum's acids. Thermal decomposition of this new Meldrum's acid derivatives generate thiocarbamoyl ketenes, which acylate amino acid esters to give pseudo tripeptides.
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Peptide modification with thiomalonoamide moiety
PublikacjaAbstract: Meldrum acid derivatives under the thermal decomposition are well known source of ketenes. Recently we investigated chemical properties of thiocarbamolyl meldrum acids. We found that 5-(α-alkylamino- α'-sulfhydryl)methylene Meldrum's acids hated in the presence of amines produce thiomalonamides. We used this reaction to the one pot synthesis of series of short peptides containing thiomalonoamide motif.
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Preparation of bicyclic β-lactam and bicyclic 1,3- oxazinone scaffolds using combined cycloaddition and metathesis processes
PublikacjaA simple, efficient two-step method for the preparation of heterobicyclic compounds was developed. Starting from 5-acyl or 5-carbamoyl-2,2- dimethyl-1,3-dioxa-4,5-dione bicyclic scaffolds of 1-azabicyclo[5.2.0]non- 3-en-9-one, 6,9,10,10a-tetrahydro-4H-[1,3]oxazino[3,2-a]azepin-4-one, and 6,9,10,10a-tetrahydro-2H-[1,3]oxazino[3,2-a]azepine-2,4(3H)-dione were prepared using cycloaddition of thermally generated ketenes to aldimines...