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Title: | 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 Studies |
Authors: | Paul, Atish Tulshiram |
Keywords: | Pharmacy Crystal cleavage Cyclization Metals Quinolines Transfer reactions |
Issue Date: | Dec-2018 |
Publisher: | ACS |
Abstract: | We 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. |
URI: | https://pubs.acs.org/doi/full/10.1021/acsomega.8b02682 http://dspace.bits-pilani.ac.in:8080/xmlui/handle/123456789/13566 |
Appears in Collections: | Department of Pharmacy |
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