Application of organolithium and related reagents in synthesis. Part 23: Synthetic strategies based on ortho-aromatic metallation. Synthesis of 4b-arylisoindolo[2,1-a]quinoline derivatives

Authors
Epsztajn, J Jozwiak, A Koluda, P Sadokierska, I Wilkowska, ID
Citation
J. Epsztajn et al., Application of organolithium and related reagents in synthesis. Part 23: Synthetic strategies based on ortho-aromatic metallation. Synthesis of 4b-arylisoindolo[2,1-a]quinoline derivatives, TETRAHEDRON, 56(27), 2000, pp. 4837-4844
Citations number
57
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
27
Year of publication
2000
Pages
4837 - 4844
Database
ISI
SICI code
0040-4020(20000630)56:27<4837:AOOARR>2.0.ZU;2-R
Abstract
The synthesis of the 2-aryl-3-hydroxyisoindol-1-ones 3 and their successive conversion via the reaction with 1-methoxy-1-trimethylsilyloxyethene in th e presence of titanium(IV) chloride into 3-carboxymethylphthalimides 7 and subsequent cyclization via sequential treatment with oxalyl chloride and al uminium chloride as a way of regiospecific transformation of the benzenecar bocylic acids into the corresponding isoindolo[2,1-a]quinoline-5,11-diones 5 is described. (C) 2000 Elsevier Science Ltd. All rights reserved.