Synthesis of functionalised quinolines through tandem addition/annulation reactions of β-(2-aminophenyl)-α,β-ynones

被引:97
作者
Arcadi, A
Marinelli, F
Rossi, E
机构
[1] Univ Aquila, Fac Sci, Dipartimento Chim Ingn Chim & Mat, I-67100 Laquila, Italy
[2] Univ Milan, Ist Chim Organ, Fac Farm, I-20133 Milan, Italy
关键词
quinolines; alpha; beta-ynones; nucleophilic addition; cross coupling; palladium; tandem Diels-Alder/annulation reactions;
D O I
10.1016/S0040-4020(99)00814-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
beta-(2-aminophenyl)-alpha,beta-ynones can quickly give functionalized 2,4-disubstituted quinolines through tandem nucleophic addition/annulations reactions. Acid-catalysed cyclization of beta-(2-aminophenyl)-alpha,beta-ynones can also occur. The easy entry into 4-iodo-2-substituted-quinolines prompted the development of a one pot procedure for synthesis of 2,4-disubstituted quinolines by further elaboration by means of palladium-catalysed reactions. The exposure to basic conditions of one beta-(2-malonylamidophenyl)-alpha,beta-ynone led to a fused quinolone derivative through intramolecular Michael addition /tautomerisation/transesterification cascade reactions. Fused polycyclic quinolines can be viewed as occurring through a tandem concerted Diels-Alder/annulation reactions of beta-(2-aminophenyl)-alpha,beta-ynones with enamines, azides and nitrile oxides. (C) 1999 Elsevier Science Ltd. Ail rights reserved.
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页码:13233 / 13250
页数:18
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