SYNTHESIS OF MESOMERIC BETAINES, QUINOLIZINIUMIDES, VIA BACK-DONATED 1,6-CYCLIZATION

Authors
MATSUDA Y KATOU K NISHIYORI T UEMURA T URAKAMI M
Citation
Y. Matsuda et al., SYNTHESIS OF MESOMERIC BETAINES, QUINOLIZINIUMIDES, VIA BACK-DONATED 1,6-CYCLIZATION, Heterocycles, 45(11), 1997, pp. 2197-2208
Citations number
31
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
45
Issue
11
Year of publication
1997
Pages
2197 - 2208
Database
ISI
SICI code
0385-5414(1997)45:11<2197:SOMBQV>2.0.ZU;2-I
Abstract
The reaction of 3-aminopyridinium salts (4) with polarized olefins (2a ,b, 3) in the presence of triethylamine yielded the corresponding 3-am inopyridinium N-allylides (5). Thermolysis of 3-aminopyridinium N-ally lides (5a-c,h-j,l-n) in refluxing xylene afforded the 1,5-dipolar cycl ization products, 8-aminoindolizines (6) together with the back-donate d 1,6-cyclization products, quinoliziniumides (7). In addition, thermo lysis of N-allylides (5a-c,h-j,l-n) in refluxing AcOH gave quinolizini umides (7).