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Communication | Special issue | Vol 40, No. 1, 1995, pp.69-72
Published online, 1st January, 1970
DOI: 10.3987/COM-93-S1-1
Synthesis of Annulated 7-Aza-indolizines by Intramolecular [3+2]Cycloaddition with Pyrazinium Dicyanomethylides

Martin Engelbach, Peter Imming, Gunther Seitz*, and Ralph Tegethoff

*Institut für Pharmazeutische Chemie, Philipps-Universität, Marbacher Weg 6 D-35032 Marburg/Lahn, Germany


Thermally induced intramolecular [3+2] cycloaddition reactions of the pyrazinium dicyanomethylides (2, 9, and 15), carrying different side chains with terminal alkynes as dipolarophiles, lead lo the novel fused 7-aza-indolizines (6, 11, 12, and 18) in high yields. In a combined inter/intramolecular cycloaddition the dicyanomethylide (15b) surprisingly furnishes the bimolecular adduct (20) besides the desired tricycle (19).