Catalogo Articoli (Spogli Riviste)

OPAC HELP

Titolo:
Reverse aromatic cope rearrangement of 2-allyl-3-alkylideneindolines driven by olefination of 2-allylindolin-3-ones: Synthesis of alpha-allyl-3-indole acetate derivatives
Autore:
Kawasaki, T; Nonaka, Y; Watanabe, K; Ogawa, A; Higuchi, K; Terashima, R; Masuda, K; Sakamoto, M;
Indirizzi:
Meiji Pharmaceut Univ, Tokyo 2048688, Japan Meiji Pharmaceut Univ Tokyo Japan 2048688 eut Univ, Tokyo 2048688, Japan Kissei Pharmaceut Co Ltd, Discovery Res, R&D, Nagano 3998304, Japan KisseiPharmaceut Co Ltd Nagano Japan 3998304 R&D, Nagano 3998304, Japan
Titolo Testata:
JOURNAL OF ORGANIC CHEMISTRY
fascicolo: 4, volume: 66, anno: 2001,
pagine: 1200 - 1204
SICI:
0022-3263(20010223)66:4<1200:RACRO2>2.0.ZU;2-E
Fonte:
ISI
Lingua:
ENG
Soggetto:
CLAISEN REARRANGEMENT; ORGANIC-SYNTHESIS; WITTIG REACTION; ACID; RING; CONSTRUCTION; STEREOCHEMISTRY; PARTICIPATION; INDOLES; SYSTEMS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
67
Recensione:
Indirizzi per estratti:
Indirizzo: Kawasaki, T Meiji Pharmaceut Univ, 2-522-1 Noshio, Tokyo 2048688, Japan Meiji Pharmaceut Univ 2-522-1 Noshio Tokyo Japan 2048688 apan
Citazione:
T. Kawasaki et al., "Reverse aromatic cope rearrangement of 2-allyl-3-alkylideneindolines driven by olefination of 2-allylindolin-3-ones: Synthesis of alpha-allyl-3-indole acetate derivatives", J ORG CHEM, 66(4), 2001, pp. 1200-1204

Abstract

The reverse aromatic Cope rearrangement of 2-allyl-3-alkylideneindolines obtained by Horner-Wadsworth-Emmons olefination of 2-allylindolin-3-ones wasperformed. When 2-allylindolin-3-ones were treated with phosphonium ylidesin refluxing toluene, domino Wittig reaction and reverse aromatic Cope rearrangement took place to give alpha -allyl-3-indole acetate derivatives in good yields. The aromatization as a new driving force in the Cope rearrangement is preferable to the conjugation with the carbonyl and cyano groups and also to the alkyl substitution pattern, which are well-known driving forces.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 29/11/20 alle ore 00:55:03