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 - Funding Information:
The authors thank The University of Arizona mass spectrometry facility for HRMS and G.J.D. of Dr. Jewett’s lab group for fluorescent determinations. The Office of the Director, NIH, is thanked for funding (1RC2MH090878-01).
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
VL - 86
SP - 17550
EP - 17559
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 24
ER -