SYNTHESIS OF ANNULATED 7-AZA-INDOLIZINES BY INTRAMOLECULAR [3+2]CYCLOADDITION WITH PYRAZINIUM DICYANOMETHYLIDES

Authors
ENGELBACH M IMMING P SEITZ G TEGETHOFF R
Citation
M. Engelbach et al., SYNTHESIS OF ANNULATED 7-AZA-INDOLIZINES BY INTRAMOLECULAR [3+2]CYCLOADDITION WITH PYRAZINIUM DICYANOMETHYLIDES, Heterocycles, 40(1), 1995, pp. 69-72
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
40
Issue
1
Year of publication
1995
Pages
69 - 72
Database
ISI
SICI code
0385-5414(1995)40:1<69:SOA7BI>2.0.ZU;2-N
Abstract
Thermally induced intramolecular [3+2] cycloaddition reactions of the pyrazinium dicyanomethylides (2, 9, and 15), carrying different side c hains with terminal alkynes as dipolarophiles, lead to the novel fused 7-aza-indolizines (6, 11, 12, and 18) in high yields. In a combined i nter/intramolecular cycloaddition the dicyanomethylide (15b) surprisin gly furnishes the bimolecular adduct (20) besides the desired tricycle (19).