Cu(OAc)2 catalyzed aerobic oxidative 2-aryl-3-acylquinoline synthesis via aza-Michael addition and aldol condensation of α,β-unsaturated ketones and 2 aminobenzyl alcohols

被引:0
作者
Athira, C. S. [1 ,2 ]
Basavaraja, D. [1 ,2 ]
Valmiki, Praveen K. [1 ,2 ]
Shridevi, D. [1 ,2 ]
Somappa, Sasidhar B. [1 ,2 ]
机构
[1] CSIR Natl Inst Interdisciplinary Sci & Technol CS, Chem Sci & Technol Div, Organ Chem Sect, Thiruvananthapuram 695019, Kerala, India
[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India
关键词
2-Aryl-3-acylquinolines; Aza-Michael addition; Aldol condensation; alpha; beta-Unsaturated ketones; One-pot MCR's; QUINOLINE SYNTHESES; C-C; FRIEDLANDER; QUINAZOLINE; CYCLIZATION; INHIBITORS; ACCESS; SKRAUP; SALTS;
D O I
10.1016/j.tetlet.2022.154043
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple and efficient one-pot Cu(OAc)(2) catalyzed aerobic oxidative synthesis of 2-aryl-3-acylquinolines from 2 aminobenzyl alcohols and a,b-unsaturated ketones is described. The protocol proceeds via cascade procedure including oxidation of 2 aminobenzyl alcohols, aza-Michael addition and aldol condensation. The reaction progressed well with alpha,beta-unsaturated ketone bearing electron-donating and electronwithdrawing substituents affording the corresponding products in good to moderate yields. In addition, the selected 2-aryl-3-acylquinolines were further subjected for diversification leading to the functionalised hybrids of 2-aryl-3-acylquinolines. Atom and step-economic, broad substrate scope, and operational simplicity is advantageous which offer an alternative way for the synthesis of 2-aryl-3acylquinolines. (C) 2022 Elsevier Ltd. All rights reserved.
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页数:7
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