Nucleophilic Addition of 2-Indolylacyl Anion Equivalents to N-Alkylpyridinium Salts

Article abstract of DOI:10.1021/jo00036a015

The reactions of the anions derived from dithioacetals 1-3 and α-amino nitriles 4 toward pyridinium salts 5 are studied.Depending on the nucleophile used, 2-(dihydropyridylmethyl)indoles 6 and 7, which can be cyclized to tetracyclic methanoazocinindole systems 10 and 11, respectively, or 2-substituted 3-(dihydropyridyl)indoles 8 and 9 are formed.