TY - JOUR
T1 - Sequential Knoevenagel [4+1] Cycloaddition–Condensation–Aza-Friedel–Crafts Intramolecular Cyclization
T2 - A 4-Center-3-Component Reaction Toward Tunable Fluorescent Indolizine Tetracycles
AU - Bedard, Nathan
AU - Foley, Christopher
AU - Davis, Garrett J.
AU - Jewett, John C.
AU - Hulme, Christopher
N1 - Publisher Copyright:
© 2021 American Chemical Society
PY - 2021/12/17
Y1 - 2021/12/17
N2 - A two-step multicomponent reaction oxidation protocol is reported herein, which affords novel tunable fluorescent tetracyclic indolizines. The procedure involves a novel 4-center-3-component reaction, which proceeds via a sequential Knoevenagel condensation, [4+1] cycloaddition, and imine condensation to afford imino-indolizines. Products then undergo cyclization and are oxidized in situ to afford fluorescent tetracycles, which are readily tunable through modification of diversity elements.
AB - A two-step multicomponent reaction oxidation protocol is reported herein, which affords novel tunable fluorescent tetracyclic indolizines. The procedure involves a novel 4-center-3-component reaction, which proceeds via a sequential Knoevenagel condensation, [4+1] cycloaddition, and imine condensation to afford imino-indolizines. Products then undergo cyclization and are oxidized in situ to afford fluorescent tetracycles, which are readily tunable through modification of diversity elements.
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U2 - 10.1021/acs.joc.1c01280
DO - 10.1021/acs.joc.1c01280
M3 - Article
AN - SCOPUS:85120648877
SN - 0022-3263
VL - 86
SP - 17550
EP - 17559
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 24
ER -