Abstract
The cycloaddition reaction of non-stabilized azomethine ylides, generated through decarboxylation and deprotonation, with (E)-2-arylidene-1-tetralones as dipolarophile has been investigated. A high degree of regioselectivity has been observed in the synthesis of a new class of functionalised dispiroheterocyclic compounds bearing a tetralone, acenapthenequinone and oxindole framework.
Highlights
Spiro compounds represent an important class of naturally occurring substances characterized by highly pronounced biological properties.[1,2,3] The most developed avenue for the synthesis of these compounds depends on the cycloaddition to an exocyclic bond.[4,5,6] highly substituted spiropyrrolidines are known, there seems to be no report on the synthesis of dispiro substituted pyrrolidine heterocycles. 1,3-Dipolar cycloaddition provides a way for the synthesis of many dispiroheterocycles through the cycloaddition reaction of nonstabilised azomethine ylides with the olefinic dipolarophiles
Highly substituted spiropyrrolidines are known, there seems to be no report on the synthesis of dispiro substituted pyrrolidine heterocycles. 1,3-Dipolar cycloaddition provides a way for the synthesis of many dispiroheterocycles through the cycloaddition reaction of nonstabilised azomethine ylides with the olefinic dipolarophiles
As a part of our study[9,10] on the synthesis of novel dispiropyrrolidinyl derivatives we have examined the 1,3-dipolar cycloaddition reaction of E-2-arylidene-1-tetralones with the azomethine ylide generated through a decarboxylation and deprotonation method
Summary
Spiro compounds represent an important class of naturally occurring substances characterized by highly pronounced biological properties.[1,2,3] The most developed avenue for the synthesis of these compounds depends on the cycloaddition to an exocyclic bond.[4,5,6] highly substituted spiropyrrolidines are known, there seems to be no report on the synthesis of dispiro substituted pyrrolidine heterocycles. 1,3-Dipolar cycloaddition provides a way for the synthesis of many dispiroheterocycles through the cycloaddition reaction of nonstabilised azomethine ylides with the olefinic dipolarophiles. As a part of our study[9,10] on the synthesis of novel dispiropyrrolidinyl derivatives we have examined the 1,3-dipolar cycloaddition reaction of E-2-arylidene-1-tetralones with the azomethine ylide generated through a decarboxylation and deprotonation method. Decarboxylative method The 1,3–dipolar cycloaddition reactions of E-2-arylidene-1-tetralones with non-stabilized azomethine ylides, generated by decarboxylative condensation of the bifunctional ketone, acenaphthenequinone, with secondary amino acids, gave a series of novel dispiropyrrolidinyl derivatives in good yield.
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