Visible-Light-Induced Metal- and Photocatalyst-Free Radical Cascade Cyclization of Cinnamamides for Synthesis of Functionalized Dihydroquinolinones

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dc.contributor.authorNishad, Chandra Shekhar
dc.contributor.authorSuman, Pallav
dc.contributor.authorSaha, Himadri
dc.contributor.authorBanerjee, Biplab
dc.date.accessioned2024-01-21T10:33:09Z
dc.date.accessioned2024-08-13T11:16:21Z
dc.date.available2024-01-21T10:33:09Z
dc.date.available2024-08-13T11:16:21Z
dc.date.issued2023-07-18T00:00:00
dc.description.abstractVisible-light-promoted metal- and photocatalyst-free radical cascade cyclization of cinnamamides with ?-oxocarboxylic acids is described for sustainable synthesis of diverse pharmaceutically important dihydroquinolinone scaffolds in one pot under mild conditions. The decarboxylative cascade cyclization proceeded efficiently at room temperature without the need for expensive photocatalysts such as Ir or Ru complexes, which indicates the practicability and environmentally benign nature of this protocol. Preliminary mechanistic studies reveal that the blue LED irradiation efficiently cleaves the I-O bond of the hypervalent iodine reagent PhI(O2CCOAr)2 formed through ligand exchange between iodobenzene diacetate and arylglyoxylic acid to initiate the cascade reaction. The synthetic value of this operationally simple and energy-efficient method is further demonstrated by late-stage functionalization of drug molecules in excellent yields. � 2023 American Chemical Society.en_US
dc.identifier.doi10.1021/acs.joc.3c00987
dc.identifier.issn223263
dc.identifier.urihttp://10.2.3.109/handle/32116/3280
dc.identifier.urlhttps://pubs.acs.org/doi/10.1021/acs.joc.3c00987
dc.language.isoen_USen_US
dc.publisherAmerican Chemical Societyen_US
dc.subjectCyclizationen_US
dc.subjectEnergy efficiencyen_US
dc.subjectIridium compoundsen_US
dc.subjectRuthenium compoundsen_US
dc.subjectScaffoldsen_US
dc.subject1 benzyl 3 (4 bromobenzoyl) 4 phenyl 3,4 dihydroquinolin 2(1h) oneen_US
dc.subject1 methyl 3 (2 methylbenzoyl) 4 phenyl 3,4 dihydroquinolin 2(1h) oneen_US
dc.subject1 methyl 3 (4 methylbenzoyl) 4 phenyl 3,4 dihydro 1,8 naphthyridin 2(1h) oneen_US
dc.subject1 methyl 3 (4 methylbenzoyl) 4 phenyl 3,4 dihydroquinolin 2(1h) oneen_US
dc.subject1 methyl 4 phenyl 3 (thiophene 2 carbonyl) 3,4 dihydroquinolin 2(1h) oneen_US
dc.subject1 methyl 4 phenyl 3 [4 (trifluoromethyl)benzoyl] 3,4 dihydroquinolin 2(1h) oneen_US
dc.subject2 [3 (4 bromobenzoyl) 2 oxo 4 phenyl 3,4 dihydroquinolin 1(2h) yl]ethyl 2 (6 methoxynaphthalen 2 yl)propanoateen_US
dc.subject2 [3 (4 methylbenzoyl) 2 oxo 4 phenyl 3,4 dihydroquinolin 1(2h) yl]ethyl 2 (6 methoxynaphthalen 2 yl)propanoateen_US
dc.subject3 (4 bromobenzoyl) 1 ethyl 4 phenyl 3,4 dihydroquinolin 2(1h) oneen_US
dc.subject3 (4 bromobenzoyl) 1 methyl 4 phenyl 3,4 dihydroquinolin 2(1h) oneen_US
dc.subject3 (4 bromobenzoyl) 6 fluoro 4 (2 methoxyphenyl) 1 methyl 3,4 dihydroquinolin 2(1h) oneen_US
dc.subject3 (4 bromobenzoyl) 6 methoxy 1 methyl 4 (4 tolyl) 3,4 dihydroquinolin 2(1h) oneen_US
dc.subject3 (4 methoxybenzoyl) 1 methyl 4 phenyl 3,4 dihydroquinolin 2(1h) oneen_US
dc.subject3 acetyl 1 methyl 4 phenyl 3,4 dihydroquinolin 2(1h) oneen_US
dc.subject3 benzoyl 1 ethyl 4 phenyl 3,4 dihydroquinolin 2(1h) oneen_US
dc.subject3 benzoyl 1 methyl 4 phenyl 3,4 dihydroquinolin 2(1h) oneen_US
dc.subject3 benzoyl 1,5,7 trimethyl 4 phenyl 3,4 dihydroquinolin 2(1h) oneen_US
dc.subject3 benzoyl 4 (4 bromo 2 fluorophenyl) 1,5,7 trimethyl 3,4 dihydroquinolin 2(1h) oneen_US
dc.subject3 benzoyl 6 bromo 1,5 dimethyl 4 phenyl 3,4 dihydroquinolin 2(1h) oneen_US
dc.subject3 benzoyl 6 fluoro 1 methyl 4 phenyl 3,4 dihydroquinolin 2(1h) oneen_US
dc.subject3 benzoyl 6 fluoro 4 (2 methoxyphenyl) 1 methyl 3,4 dihydroquinolin 2(1h) oneen_US
dc.subject3 benzoyl 6 methoxy 1 methyl 4 phenyl 3,4 dihydroquinolin 2(1h) oneen_US
dc.subject4 (2,3 dimethoxyphenyl) 6 fluoro 3 (4 methoxybenzoyl) 1 methyl 3,4 dihydroquinolin 2(1h) oneen_US
dc.subject4 (4 bromo 2 fluorophenyl) 1,5,7 trimethyl 3 (4 methylbenzoyl) 3,4 dihydroquinolin 2(1h) oneen_US
dc.subject4 (4 bromo 2 fluorophenyl) 1,5,7 trimethyl 3 [4 (trifluoromethyl)benzoyl] 3,4 dihydroquinolin 2(1h) oneen_US
dc.subject6 methoxy 3 (4 methoxybenzoyl) 1 methyl 4 phenyl-3,4 dihydroquinolin 2(1h) oneen_US
dc.subject6 methyl 8 (4 methylbenzoyl) 9 [3 (trifluoromethyl)phenyl] 2,3,8,9 tetrahydro[1,4]dioxino[2,3 g]quinolin 7(6h) oneen_US
dc.subject8 (3,4 dimethoxybenzoyl) 6 methyl 9 [3 (trifluoromethyl)phenyl] 2,3,8,9 tetrahydro[1,4]dioxino[2,3 g]quinolin 7(6h) oneen_US
dc.subject8 benzoyl 6 (prop 2 yn 1 yl) 9 [3 (trifluoromethyl)phenyl] 2,3,8,9 tetrahydro[1,4]dioxino[2,3 g]quinolin 7(6h) oneen_US
dc.subject8 benzoyl 6 methyl 9 [3 (trifluoromethyl)phenyl] 2,3,8,9 tetrahydro[1,4]dioxino[2,3 g]quinolin 7(6h) oneen_US
dc.subjectacetoacetic aciden_US
dc.subjectamideen_US
dc.subjectcarboxylic acid derivativeen_US
dc.subjectcinnamic acid derivativeen_US
dc.subjectdihydroquinoline derivativeen_US
dc.subjectethyl 2 (3 benzoyl 2 oxo 4 phenyl 3,4 dihydroquinolin 1 (2h) yl]acetateen_US
dc.subjectethyl 2 [3 benzoyl 4 (4 bromo 2 fluorophenyl) 5,7 dimethyl 2 oxo 3,4 dihydroquinolin 1(2h) yl]acetateen_US
dc.subjectethyl 2 [4 (4 bromo 2 fluorophenyl) 5,7 dimethyl 3 (4 methylbenzoyl) 2 oxo 3,4 dihydroquinolin 1(2h) yl]acetateen_US
dc.subjectfree radicalen_US
dc.subjectfunctional groupen_US
dc.subjectglyoxylic aciden_US
dc.subjectiodineen_US
dc.subjectiodobenzeneen_US
dc.subjectiridium complexen_US
dc.subjectliganden_US
dc.subjectmetalen_US
dc.subjectn methyl 2 [3 (4 methylbenzoyl) 2 oxo 4 phenyl 3,4 dihydroquinolin 1(2h) yl] n [3 phenyl 3 [4 (trifluoromethyl)phenoxy]propyl]acetamideen_US
dc.subjectphenylglyoxylic aciden_US
dc.subjectreagenten_US
dc.subjectruthenium complexen_US
dc.subjectunclassified drugen_US
dc.subjectCascade cyclizationen_US
dc.subjectConditionen_US
dc.subjectEnvironmentally benignen_US
dc.subjectFunctionalizeden_US
dc.subjectIr complexesen_US
dc.subjectMechanistic studiesen_US
dc.subjectOne poten_US
dc.subjectRu complexesen_US
dc.subjectVisible lighten_US
dc.subjectVisible light induceden_US
dc.subjectArticleen_US
dc.subjectchemical bonden_US
dc.subjectcomplex formationen_US
dc.subjectconjugationen_US
dc.subjectcontrolled studyen_US
dc.subjectcyclizationen_US
dc.subjectdecarboxylationen_US
dc.subjectdrug synthesisen_US
dc.subjectelectrophilicityen_US
dc.subjectone pot synthesisen_US
dc.subjectphotocatalysisen_US
dc.subjectreaction analysisen_US
dc.subjectreaction optimizationen_US
dc.subjectregioselectivityen_US
dc.subjectroom temperatureen_US
dc.subjectFree radicalsen_US
dc.titleVisible-Light-Induced Metal- and Photocatalyst-Free Radical Cascade Cyclization of Cinnamamides for Synthesis of Functionalized Dihydroquinolinonesen_US
dc.title.journalJournal of Organic Chemistryen_US
dc.typeArticleen_US
dc.type.accesstypeClosed Accessen_US

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