Alkylation of tetrazolo[1,5-a]pyridine and its Benzologues (Annelation Effect)

A. Messmer, G. Y. Hajös, Z. S. Juhász-Riedl, P. Sohár

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25 Citations (Scopus)


Tetrazolo[1,5-a]pyridine (1) and its angularly and linearly fused benzologues tetrazolo[1,5-a]quinoline (4), tetrazolo[5,1-a]isoquinoline (7), and tetrazolo [1,5-b]isoquinoline (10), respectively, were alkylated by methyl iodide, dimethyl sulfate, trimethyloxonium, and triethyloxonium salts to give mixtures of 1- and 2-alkyl compounds in different ratios. While tetrazoles 1 and 4 afforded mainly 1-alkyl compounds, tetrazole 7 yielded predominantly 2-alkyl compound. Comparison of the linearly (10) and angularly fused (4 and 7) analogues showed that besides steric factors the annelation effect influences also the regioselectivity of these reactions. A satisfactory correlation was found between densities of the MO representations of the lone electron pairs calculated by CNDO/2 and the experimental findings.

Original languageEnglish
Pages (from-to)973-975
Number of pages3
JournalJournal of Organic Chemistry
Issue number5
Publication statusPublished - Oct 1 1988

ASJC Scopus subject areas

  • Organic Chemistry

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