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Annulation reactions of 3‐aminoisoquinolin‐l(2 H )‐one. Synthesis of pyrimido[1,2‐ b ]isoquinolines, pyrido‐[2,3‐ c ]isoquinolines and pyrrolo[2,3‐ c ]isoquinolines
Author(s) -
Deady Leslie W.,
Quazi Nurul H.
Publication year - 1994
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.5570310417
Subject(s) - chemistry , isoquinoline , annulation , bromide , malonic acid , medicinal chemistry , stereochemistry , organic chemistry , catalysis
Reactions of the title compound with the malonic acid derivatives diethyl ethoxymethylenemalonate (EMME), ethyl ethoxymethylenecyanoacetate (EMCA) and ethoxymethylenemalononitrile (EMMN) are reported. Condensations occur at the amino group or C‐4, depending on conditions and the former intermediate was successfully cyclized to the pyrimido[1,2‐ b ]isoquinoline system. Reactions with 2,4‐pentanedione and p ‐bromophenacyl bromide gave only the angular systems, pyrido[2,3‐ c ]isoquinoline and pyrrolo[2,3‐ c ]isoquin‐oline, respectively.