Linearly fused isoquinolines. 3. Positional effect of substitution on equilibrium of tetrazole-azide systems. Anomalous behavior in trifluoroacetic acid

András Messmer, G. Hajós

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Abstract

A new method for synthesis of heteroaromatic azides has been elaborated, and a series of substituted tetrazolo[1,5-b]isoquinoline derivatives has been synthesized. The effect of R1 and R4 substituents on the equilibrium between 3-azidoisoquinoline (1b) and tetrazol[1,5-b]isoquinoline (1a) was investigated. Only a slight difference in influence of substituents in the opposite positions R1 and R4 was found. In contrast to earlier examples, the equilibria discussed here are shifted to the tetrazole form in TFA!

Original languageEnglish
Pages (from-to)843-846
Number of pages4
JournalJournal of Organic Chemistry
Volume46
Issue number5
Publication statusPublished - 1981

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Isoquinolines
Trifluoroacetic Acid
Azides
Substitution reactions
Derivatives
1H-tetrazole
isoquinoline

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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AB - A new method for synthesis of heteroaromatic azides has been elaborated, and a series of substituted tetrazolo[1,5-b]isoquinoline derivatives has been synthesized. The effect of R1 and R4 substituents on the equilibrium between 3-azidoisoquinoline (1b) and tetrazol[1,5-b]isoquinoline (1a) was investigated. Only a slight difference in influence of substituents in the opposite positions R1 and R4 was found. In contrast to earlier examples, the equilibria discussed here are shifted to the tetrazole form in TFA!

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