Regiodivergent Synthesis of Densely Functionalized Indolizines via (2 + 2 + 1) Cycloaddition

Regiodivergent Synthesis of Densely Functionalized Indolizines via (2 + 2 + 1) Cycloaddition

A novel metal and additive free, atom-economic method for the regiodivergent synthesis of crucial 6- or 8-substituted indolizine from meta-amide-substituted pyridine and alkyne via a [2 + 2 + 1] cycloaddition is developed. The reaction proceeds through the cleavage of the carbon–carbon triple bond....

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Veröffentlicht in:Journal of organic chemistry 2023-06, Vol.88 (11), p.6805-6815
Hauptverfasser: Tiwari, Shashikant, Rawat, Diwan S.
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container_title Journal of organic chemistry
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creator Tiwari, Shashikant
Rawat, Diwan S.
description A novel metal and additive free, atom-economic method for the regiodivergent synthesis of crucial 6- or 8-substituted indolizine from meta-amide-substituted pyridine and alkyne via a [2 + 2 + 1] cycloaddition is developed. The reaction proceeds through the cleavage of the carbon–carbon triple bond. The synthesized product contains an important amide group that can be further functionalized to afford biologically active compounds.
doi_str_mv 10.1021/acs.joc.3c00114
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title Regiodivergent Synthesis of Densely Functionalized Indolizines via (2 + 2 + 1) Cycloaddition
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