SYNTHESIS OF 2,3-FUSED QUINOLINES FROM 3-SUBSTITUTED QUINOLINE 1-OXIDES .3. INTRAMOLECULAR CYCLIZATION OF QUINOLINE 1-OXIDES BEARING ACTIVEMETHYLENE GROUPS AT THE 3-POSITION IN THE PRESENCE OF ACETIC-ANHYDRIDE

Authors
MIURA Y FUJIMURA Y TAKAKU S HAMANA M
Citation
Y. Miura et al., SYNTHESIS OF 2,3-FUSED QUINOLINES FROM 3-SUBSTITUTED QUINOLINE 1-OXIDES .3. INTRAMOLECULAR CYCLIZATION OF QUINOLINE 1-OXIDES BEARING ACTIVEMETHYLENE GROUPS AT THE 3-POSITION IN THE PRESENCE OF ACETIC-ANHYDRIDE, Heterocycles, 35(2), 1993, pp. 693-699
Citations number
5
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
35
Issue
2
Year of publication
1993
Pages
693 - 699
Database
ISI
SICI code
0385-5414(1993)35:2<693:SO2QF3>2.0.ZU;2-1
Abstract
3-N-Alkylcyanoacetamidoquinoline 1-oxides (3a and 3c) react with Ac2O at room temperature in chloroform to afford 1-alkyl-3-cyano-4H-pyrrolo [3,2-b]quinolin-2-ones (4a and 4c). The cyclization of 3-N-alkylethoxy carbonylacetamidoquinoline 1-oxides (3b and 3d) occurs upon heating wi th Ac2O at 60-degrees-C. 3-(3,3-Dicyanopropoxy) quinoline 1-oxide (5) also cyclizes to the pyranoquinoline (6) when treated with Ac2O at roo m temperature in chloroform-DMF.