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Synthesis
DOI: 10.1055/a-2661-4104
DOI: 10.1055/a-2661-4104
Paper
High-Yielding Regioselective Synthesis of Coumarin/2-Quinolone C3–C4 Fused 5-Substituted-1,4-Benzodiazepine Scaffolds
Supported by: Science and Engineering Research Board DST/SERB-EMR/2015/000466
Abstract
Herein, we report an unprecedented route for the high-yielding regioselective synthesis of coumarin/2-quinolone C3–C4 fused 5-substituted-1,4-benzodiazepine scaffolds via indium chloride-mediated Pictet–Spengler type cycloannulation of 3-amino-4-(phenylamino)-coumarin/2-quinolone and aryl/heterocyclic aldehydes through the transitory intermediacy of the cyclic diamine–indium complex. Also, a plausible mechanistic pathway has been proposed from control experiments and HRMS analysis of reactive intermediates. This robust protocol eases access to the structurally diversified, privileged, seven-membered skeleton with an excellent step economy.
Keywords
Coumarin/2-quinolone - Regioselective synthesis - Indium(III) chloride - Cyclic diamine–indium complex - 1,4-BenzodiazepinesPublication History
Received: 19 June 2025
Accepted after revision: 21 July 2025
Accepted Manuscript online:
21 July 2025
Article published online:
13 August 2025
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