One-pot assembly of large heterocyclic quinones through three-component reactions

Authors
Lopez-Alvarado, P Alonso, MA Avendano, C Menendez, JC
Citation
P. Lopez-alvarado et al., One-pot assembly of large heterocyclic quinones through three-component reactions, TETRAHEDR L, 42(45), 2001, pp. 7971-7974
Citations number
29
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
45
Year of publication
2001
Pages
7971 - 7974
Database
ISI
SICI code
0040-4039(20011105)42:45<7971:OAOLHQ>2.0.ZU;2-H
Abstract
Treatment of indoles with 2,5,8-quinolinetriones in the presence of a catal ytic amount of hydrochloric acid afforded heptacyclic reaction products ari sing from a cascade of two regioselective Michael addition-Diels-Alder cycl oaddition steps. In another approach to polyheterocyclic quinone systems, d ouble Diels-Alder reactions between indolylquinolinetriones and 2,5- or 2.6 -dihalogenated benzoquinones provided regioisomeric 11-cycle products in go od yields. (C) 2001 Elsevier Science Ltd. All rights reserved.