Novel functionalization of 1-methyl-2-quinolone; dimerization and denitration of trinitroquinolone

New methods for functionalization of 1-methyl-2-quinolone (MeQone) skeleton are provided. The reaction of 1-methyl-3,6,8-trinitro-2-quinolone (TNQ) with amines affords quinolone dimer 1 and 6,8-dinitroquinolone (6,8-DNQ). Dimerization predominantly proceeds at room temperature, and denitration takes...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 2002, Vol.58 (3), p.473-478
Main Authors: Nishiwaki, Nagatoshi, Sakashita, Midori, Azuma, Mayumi, Tanaka, Chitose, Tamura, Mina, Asaka, Noriko, Hori, Kazushige, Tohda, Yasuo, Ariga, Masahiro
Format: Article
Language:English
Subjects:
cine-substitution
denitration
dimerization
nitration
trinitroquinolone
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:New methods for functionalization of 1-methyl-2-quinolone (MeQone) skeleton are provided. The reaction of 1-methyl-3,6,8-trinitro-2-quinolone (TNQ) with amines affords quinolone dimer 1 and 6,8-dinitroquinolone (6,8-DNQ). Dimerization predominantly proceeds at room temperature, and denitration takes place under heated and diluted conditions. We also provide a plausible mechanism for these reactions on the basis of structure–reactivity relationship of amines. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(01)01169-3