An anti‐Michael route for the synthesis of indole‐spiro (indene‐pyrrolidine) by 1,3‐cycloaddition of azomethineylide with indole‐derivatised olefins

One‐pot three‐component reaction for indole‐spiro (indene‐pyrrolidine) highly strained molecules were synthesized with moderate yield by 1,3‐cycloaddition of unsymmetrical dipolarophiles, prepared from indol‐3‐yl and 1‐acetyl‐1H‐indol‐3‐yl derivative with azomethineylide generated through decarboxyl...

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Bibliographic Details
Published inJournal of heterocyclic chemistry Vol. 57; no. 3; pp. 1083 - 1089
Main Author Yellappa, Shivaraj
Format Journal Article
LanguageEnglish
Published HOBOKEN Wiley 01.03.2020
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Subjects
Alkenes
Chemical synthesis
Chemistry
Chemistry, Organic
Cycloaddition
Indene
Physical Sciences
Science & Technology
Spiro compounds
Viability
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Summary:One‐pot three‐component reaction for indole‐spiro (indene‐pyrrolidine) highly strained molecules were synthesized with moderate yield by 1,3‐cycloaddition of unsymmetrical dipolarophiles, prepared from indol‐3‐yl and 1‐acetyl‐1H‐indol‐3‐yl derivative with azomethineylide generated through decarboxylative addition of amino acid sarcosine and ninhydrine, which is confirmed by NOESY. Our method is to demonstrate an efficient path in the preparation of strained organic spiro compound, an atom‐economical process and eco‐friendly toward environment. Viability gives an access to prepare of various spiro pharmaceutical drug molecules.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.3843