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 | Zendy

Gaurav Joshi | Zendy; Aabid A. Wani | Zendy; Sahil Sharma | Zendy; Priyadeep Bhutani | Zendy; Prasad V. Bharatam | Zendy; Atish T. Paul | Zendy; Raj Kumar | Zendy

Open Access

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

Author(s) -

Gaurav Joshi,

Aabid A. Wani,

Sahil Sharma,

Priyadeep Bhutani,

Prasad V. Bharatam,

Atish T. Paul,

Raj Kumar

Publication year - 2018

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.8b02682

Subject(s) - isomerization , chemistry , aryl , intramolecular force , yield (engineering) , cleavage (geology) , density functional theory , medicinal chemistry , stereochemistry , reaction mechanism , decomposition , combinatorial chemistry , computational chemistry , organic chemistry , catalysis , alkyl , materials science , geotechnical engineering , fracture (geology) , engineering , metallurgy

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.

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