A Diastereoselective Synthesis of Dispiro[oxindole-cyclohexanone]pyrrolidines by 1,3-Dipolar Cycloaddition.

نویسندگان

  • Alexander Anis'kov
  • Irina Klochkova
  • Roman Tumskiy
  • Alevtina Yegorova
چکیده

For the first time, arylmethylidene cyclohexanones that are non-symmetrical due to the presence of peripheral substituents were studied in 1,3-dipolar cycloaddition reactions. It is shown that the interaction with the azomethine ylide generated from sarcosine proceeds regio- and diastereoselectively, with the participation of two non-equivalent parts of the dipolarophile. Also for the first time, β-amino ketones (Mannich bases) were used as dipolarophile equivalents of unsaturated ketones. It was found that cycloaddition occurs diastereoselectively at the generated center.

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منابع مشابه

1,3-Dipolar Cycloaddition Reaction of Dibenzalaceton with Non-stabilized Azomethinylides: Synthesis of New Spirooxindolo(pyrrolizidines/ pyrrolidines)

1,3-dipolar cycloaddition reaction of 1 mol or 2 mol of dibenzalaceton with 1 mol of non-stabilized azomethinylides generated in situ by decarboxylative condensation of isatin and proline or sarcosine give the novel new spiro-oxindolo(pyrrolizidines/ pyrrolidines) instead of bis-spirooxindolo( pyrrolizidines/ pyrrolidines).

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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...

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1,3-Dipolar Cycloaddition Reaction of Dibenzalaceton with Non-stabilized Azomethinylides: Synthesis of New Spirooxindolo(pyrrolizidines/ pyrrolidines)

1,3-dipolar cycloaddition reaction of 1 mol or 2 mol of dibenzalaceton with 1 mol of non-stabilized azomethinylides generated in situ by decarboxylative condensation of isatin and proline or sarcosine give the novel new spiro-oxindolo(pyrrolizidines/ pyrrolidines) instead of bis-spirooxindolo( pyrrolizidines/ pyrrolidines).

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An efficient one-pot synthesis of C2-symmetric pyrrolidines and dispiro pyrrolidines/pyrrolizidines through 1,3-dipolar cycloaddition reaction

A facile and efficient one-pot synthesis of pyrrolidines and dispiro pyrrolidines/pyrrolizidines has been accomplished by the 1,3-dipolar cycloaddtion reaction of azomethine ylides generated insitu from paraformaldehyde/ninhydrin and secondary amino acids with electron-deficient dipolarophiles in good yield. The reaction proceeded with high regio and stereoselectivity. The products have been ch...

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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...

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عنوان ژورنال:
  • Molecules

دوره 22 12  شماره 

صفحات  -

تاریخ انتشار 2017