Journal of Heterocyclic Chemistry

Cycloaddition reactions of N??p??toluenesulfonylimino derivatives of quinoline and isoquinoline. A route to pyrazolo [1, 5??a] quinolines and pyrazolo [5, 1??a] …

RJ Sundberg, JE Ellis

Index: Sundberg, Richard J.; Ellis, James E. Journal of Heterocyclic Chemistry, 1982 , vol. 19, p. 573 - 576

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Citation Number: 18

Abstract

Abstract Np-Toluenesulfonylimino ylides of quinoline and isoquinoline give cycloadducts with electrophilic acetylenes at 105. The adducts are spontaneously aromatized under the conditions of their formation by elimination of p-toluenesulfmic acid to give pyrazolo [1, 5-a] quinolines and pyrazolo [5, 1-a] isoquinolines, respectively. The orientation of cycloaddition is the same as for N-amino ylides for acetylenic esters. The ad-ducts from p- ...