Joshi, GWani, A.A.Sharma, SBhutani, PBharatam, P.V.Paul, A.T.Kumar, R.2019-03-262024-08-132019-03-262024-08-132018Joshi, G., Wani, A.A., Sharma, S and 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 Studies. ACS Omega.Vol. 3(12), PP. 18783-18790. 10.1021/acsomega.8b02682Online- 2470-134310.1021/acsomega.8b02682https://kr.cup.edu.in/handle/32116/2241We 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.enHeterocyclic compoundsMichael reactionPhysical and chemical processesReaction mechanismRedox reactionArticlehttps://pubs.acs.org/doi/10.1021/acsomega.8b02682