An Improved Environmentally Friendly Approach to 4-Nitro-, 4-Sulfonyl-, and 4-Aminoquinolines and 4-Quinolones through Conjugate Addition of Nucleophiles to β-(2-Aminophenyl)-α,β-ynones

被引：25

作者：

Rode, Navnath D. ^{[1
]}

Arcadi, Antonio ^{[1
]}

Chiarini, Marco ^{[2
]}

Marinelli, Fabio ^{[1
]}

机构：

[1] Univ Aquila, Dipartimento Sci Fis & Chim, Via Vetoio, I-67010 Coppito, AQ, Italy

[2] Univ Teramo, Fac Biosci & Tecnol Agroalimentari & Ambientali, Via R Balzarini 1, I-64100 Teramo, Te, Italy

来源：

SYNTHESIS-STUTTGART | 2017年 / 49卷 / 11期

关键词：

nitroquinolines; tosylquinolines; aminoquinolines; quinolones; ynones; ORGANOBORON DERIVATIVES; EFFICIENT SYNTHESIS; CYCLIZATION; QUINOLINES; SULFONES; HETEROCYCLIZATION; CONDENSATION; FLUORINATION; NITROARENES;

D O I：

10.1055/s-0036-1588147

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sequential addition/annulation reactions of sulfinate and nitrite anions to beta-(2-aminophenyl)-alpha,beta-ynones led to valuable 4-sulfonylquinolines and 4-nitroquinolines. The latter proved to be versatile precursors of N-unsubstituted 4-aminoquinolines and 4-quinolones. Reaction of beta-(2-aminophenyl)-alpha,beta-ynones with DMF/NaOH resulted in the formation of 4-(dimethylamino)quinolines. The use of an alternative CO-free procedure for the preparation of substrates beta-(2-aminophenyl)-alpha,beta-ynones allowed extension of the methodology to the synthesis of 4-substituted 2-alkylquinolines.

引用

页码：2501 / 2512

页数：12

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