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Pyrido[2′1′:2,3]imidazo[4,5‐ c ]isoquinoline and the alkylation of pyrido[2′,1′:2,3]imidazo[4,5‐ c ]isoquinolin‐5(6 H )‐one
Author(s) -
Paolini John P.,
Palopoli Frank P.,
Lendvay Louis J.,
Huffman John
Publication year - 1987
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.5570240303
Subject(s) - chemistry , isoquinoline , potassium cyanide , alkylation , isoindole , cyanide , 2 aminopyridine , potassium , medicinal chemistry , nuclear magnetic resonance spectroscopy , stereochemistry , organic chemistry , catalysis
The reaction of 2‐aminopyridine, o ‐phthaldehydic acid and potassium cyanide gave pyrido[2′,1′:2,3]imidazo[4,5‐ c ]isoquinolin‐5(6 H )‐one, which upon treatment with propargylbromide, yielded both O and N alkylated products. 2‐Aminopyridine, o ‐phthaldehyde and potassium cyanide gave 1‐cyano‐2‐(2‐pyridyl)isoindole which rearranged in acid to give the previously unreported parent pyrido[2′,1′:2,3]imidazo[4,5‐ c ]isoquinole. Structures were confirmed using uv, ir, nmr and x‐ray spectroscopy.