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.
Synthesis of functionalised quinolines through tandem addition/annulation reactions of beta-(2-aminophenyl)-alpha,beta-ynones / A. Arcadi, F. Marinelli, E. Rossi. - In: TETRAHEDRON. - ISSN 0040-4020. - 55:46(1999), pp. 13233-13250.
Titolo: | Synthesis of functionalised quinolines through tandem addition/annulation reactions of beta-(2-aminophenyl)-alpha,beta-ynones |
Autori: | |
Parole Chiave: | quinolines; alpha,beta-ynones; nucleophilic addition; cross coupling; palladium; tandem Diels-Alder/annulation reactions |
Settore Scientifico Disciplinare: | Settore CHIM/06 - Chimica Organica |
Data di pubblicazione: | 1999 |
Rivista: | |
Tipologia: | Article (author) |
Digital Object Identifier (DOI): | http://dx.doi.org/10.1016/S0040-4020(99)00814-5 |
Appare nelle tipologie: | 01 - Articolo su periodico |