Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 18, Issue 29, Pages 5688-5696Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0ob01230k
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Funding
- National Natural Science Foundation of China [21772069, 21831007]
- Six Kinds of Talents Project of Jiangsu Province [SWYY-025]
- TAPP and Undergraduate Students Project of JSNU
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A Bronsted acid-catalyzed C3-alkylation of indolizines has been established with different electrophiles such asortho-hydroxybenzyl alcohols, other precursors ofpara-quinone methides andortho-quinone methides, and 2-indolylmethanol as well. By using this approach, a series of C3-functionalized indolizines were synthesized in overall good yields (up to 89%). These examples demonstrate that the Bronsted acid-catalyzed C3-alkylation of indolizines has a wide applicability, which can serve as a useful method for synthesizing C3-functionalized indolizine derivatives with structural diversity. This reaction has fulfilled the task of developing organocatalytic C3-functionalization of indolizines for the synthesis of biologically important indolizine derivatives.
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