Synthesis of pyrrolizidines and indolizidines by multicomponent 1,3-dipolar cycloaddition of azomethine ylides
نویسندگان
چکیده
منابع مشابه
A Three-Component 1,3-Dipolar Cycloaddition Reaction of Azomethine Ylide for Synthesis of New Bis-spiro-oxindolo(pyrrolizidines/pyrrolidines) Derivatives
The development of multicomponent reactions (MCRs) designed to produce elaborate biologically active compounds has become an important area of research in organic, combinatorial, and medicinal chemistry. A comparative study of the synthesis of new bis-spiro-oxindolo(pyrrolizidines/pyrrolidines) ring systems by the cycloaddition of azomethine ylides generated by a decarboxylative route from sarc...
متن کاملMulticomponent synthesis of unnatural pyrrolizidines using 1,3-dipolar cycloaddition of proline esters.
The synthesis of unnatural pyrrolizidines has been studied using a multicomponent-domino process involving proline or 4-hydroxyproline esters, an aldehyde and a dipolarophile. The formation of the iminium salt promotes the 1,3-dipolar cycloaddition affording highly substituted pyrrolizidines under mild conditions and high regio- and diastereoselectivities.
متن کاملA Three-Component 1,3-Dipolar Cycloaddition Reaction of Azomethine Ylide for Synthesis of New Bis-spiro-oxindolo(pyrrolizidines/pyrrolidines) Derivatives
The development of multicomponent reactions (MCRs) designed to produce elaborate biologically active compounds has become an important area of research in organic, combinatorial, and medicinal chemistry. A comparative study of the synthesis of new bis-spiro-oxindolo(pyrrolizidines/pyrrolidines) ring systems by the cycloaddition of azomethine ylides generated by a decarboxylative route from sarc...
متن کامل1,3-Dipolar cycloaddition of unstabilised azomethine ylides by Lewis base catalysis.
Lewis base catalysed 1,3-dipolar cycloaddition between α,β-unsaturated acyl fluorides and N-[(trimethylsilyl)methyl]amino ethers has been achieved using 1 mol% DMAP. Competition experiments and (19)F-NMR studies indicate that the cycloaddition occurs preferentially between the α,β-unsaturated acyl fluoride and the unstabilised azomethine ylide. In addition, an enantioselective variant, using ch...
متن کاملChiral Induction in Cycloaddition Reactions of Azomethine Ylides to Synthesis of New Enantiomerically Pure Spiro Oxindolopyrrolizidines
An efficient one-pot three-component procedure for the synthesis of new chiral spiro-oxindolopyrrolizidines with highly regio-, diastereo-, and enantioselective from 1,3-dipolar cycloaddition of azomethine ylides and optically pure active cinamoyl oxazolidinone are described. The process occurs at room temperature in aqueous ethanol as green solvent and in the absence of any bidentate chelating...
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ژورنال
عنوان ژورنال: Pure and Applied Chemistry
سال: 2018
ISSN: 1365-3075,0033-4545
DOI: 10.1515/pac-2018-0710