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dc.contributor.authorJoshi, Gaurav
dc.contributor.authorWani, Aabid Abdullah
dc.contributor.authorSharma, Sahil
dc.contributor.authorBhutani, Priyadeep
dc.contributor.authorBharatam, Prasad V.
dc.contributor.authorPaul, Atish T.
dc.contributor.authorKumar, Raj
dc.date.accessioned2019-03-22T09:11:06Z
dc.date.available2019-03-22T09:11:06Z
dc.date.issued2018
dc.identifier.citationJoshi G., Wani A.A., Sharma S. et.al. (2018) Unanticipated Cleavage of 2-Nitrophenyl-Substituted N-Formyl Pyrazolines under Bechamp Conditions: Unveiling the Synthesis of 2-Aryl Quinolines and Their Mechanistic Exploration via DFT Studiesen_US
dc.identifier.issn24701343
dc.identifier.urihttp://kr.cup.edu.in/handle/32116/2074
dc.description.abstractWe herein report for the first time an unusual decomposition of 2-nitrophenyl-substituted N-formyl pyrazolines under Bechamp reduction condition employed to yield 2-aryl quinolines exclusively instead of pyrazolo[1,5-c]quinazolines. The reaction investigation suggests acid-mediated cleavage of 1 followed by a retro-Michael addition, and a subsequent in situ intramolecular reductive cyclization through a modified Friedlander mechanism afforded 2-aryl quinolines (2) in good yields. The proposed mechanistic pathways were supported via experimental evidence and density functional theory studies. B3LYP/6-31+G(d) analysis indicated the involvement of trans-2-hydroxyaminochalcone as a key intermediate and its isomerization and cyclization, leading to unusual product formation.en_US
dc.language.isoenen_US
dc.publisherAmerican Chemical Societyen_US
dc.titleUnanticipated Cleavage of 2-Nitrophenyl-Substituted N-Formyl Pyrazolines under Bechamp Conditions: Unveiling the Synthesis of 2-Aryl Quinolines and Their Mechanistic Exploration via DFT Studiesen_US
dc.typeArticleen_US
dc.identifier.doi10.1021/acsomega.8b02682
dc.title.journalACS Omega
dc.type.accesstypeOpen Accessen_US


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