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在贝尚普条件下2-硝基苯基取代的α-甲酰基吡唑啉的意外裂解：2-芳基喹啉的合成及其通过密度泛函理论研究的机理探索

Unanticipated Cleavage of 2-Nitrophenyl-Substituted -Formyl Pyrazolines under Bechamp Conditions: Unveiling the Synthesis of 2-Aryl Quinolines and Their Mechanistic Exploration via DFT Studies.

作者信息

Joshi Gaurav, Wani Aabid Abdullah, Sharma Sahil, Bhutani Priyadeep, Bharatam Prasad V, Paul Atish T, Kumar Raj

机构信息

Department of Pharmaceutical Sciences and Natural Products, Central University of Punjab, Bathinda 151001, Punjab, India.

Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), S.A.S. Nagar, Mohali 160062, India.

出版信息

ACS Omega. 2018 Dec 28;3(12):18783-18790. doi: 10.1021/acsomega.8b02682. eCollection 2018 Dec 31.

DOI:10.1021/acsomega.8b02682
PMID:31458441
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6643473/
Abstract

We herein report for the first time an unusual decomposition of 2-nitrophenyl-substituted -formyl pyrazolines under Bechamp reduction condition employed to yield 2-aryl quinolines exclusively instead of pyrazolo[1,5-]quinazolines. The reaction investigation suggests acid-mediated cleavage of followed by a retro-Michael addition, and a subsequent in situ intramolecular reductive cyclization through a modified Friedlander mechanism afforded 2-aryl quinolines () 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.

摘要

我们在此首次报道，在用于仅生成2-芳基喹啉而非吡唑并[1,5-]喹唑啉的贝尚还原条件下，2-硝基苯基取代的甲酰基吡唑啉发生了不寻常的分解。反应研究表明，在酸介导下断裂，随后进行逆迈克尔加成，接着通过改进的弗里德兰德机理进行原位分子内还原环化，以良好的产率得到了2-芳基喹啉（）。所提出的机理途径得到了实验证据和密度泛函理论研究的支持。B3LYP/6-31+G(d)分析表明反式-2-羟基氨基查尔酮作为关键中间体的参与及其异构化和环化，导致了不寻常产物的形成。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6ef5/6643473/edfb525389df/ao-2018-02682h_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6ef5/6643473/f32d07716618/ao-2018-02682h_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6ef5/6643473/63fd9df5fdea/ao-2018-02682h_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6ef5/6643473/0aaba6e2c20b/ao-2018-02682h_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6ef5/6643473/44a1d79a54d0/ao-2018-02682h_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6ef5/6643473/4d7286a1b6a5/ao-2018-02682h_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6ef5/6643473/edfb525389df/ao-2018-02682h_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6ef5/6643473/f32d07716618/ao-2018-02682h_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6ef5/6643473/63fd9df5fdea/ao-2018-02682h_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6ef5/6643473/0aaba6e2c20b/ao-2018-02682h_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6ef5/6643473/44a1d79a54d0/ao-2018-02682h_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6ef5/6643473/4d7286a1b6a5/ao-2018-02682h_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6ef5/6643473/edfb525389df/ao-2018-02682h_0006.jpg

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