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1,3‐Dipolar cycloaddition reaction of phenanthridinium N ‐imines and N ‐benzoylimine with acetylenic compounds
Author(s) -
Tamura Yasumitsu,
Miki Yasuyoshi,
Nishikawa Yoshinori,
Ikeda Masazumi
Publication year - 1976
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570130223
Subject(s) - dimethyl acetylenedicarboxylate , chemistry , phenanthridine , cycloaddition , medicinal chemistry , potassium carbonate , salt (chemistry) , potassium , aromatization , organic chemistry , catalysis
N ‐Aminophenanthridinium salt reacted with dimethyl acetylenedicarboxylate in the presence of potassium carbonate to give a 3,3a‐dihydropyrazolo[1,5‐ f ]phenanthridine but with mono‐substituted acetylenes (ethyl propiolate and benzoylacetylene) it produced aromatized pyrazolo‐[1,5‐ f ]phenanthridines (XII and XIII). The reaction of the N ‐benzoylimine with di‐substituted acetylenes (dimethyl acetylenedicarboxylate and methyl phenylpropiolate) and mono‐substituted acetylenes (ethyl propiolate and benzoylacetylene) yielded 1,3a‐dihydropyrazolo[1,5‐ f ]phenanthridines and the aromatized products (XII and XIII), respectively.