1,3‐Dipolar cycloaddition reaction of phenanthridinium  N ‐imines and  N ‐benzoylimine with acetylenic compounds | Zendy

Tamura Yasumitsu | Zendy; Miki Yasuyoshi | Zendy; Nishikawa Yoshinori | Zendy; Ikeda Masazumi | Zendy

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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.

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