75586-29-7Relevant academic research and scientific papers
The Reactions of 2-Alkynylbenzaldehydes with Hydrazides: a Route to Isoquinoline N-Imines
Anderson, Patrick N.,Sharp, John T.
, p. 1331 - 1334 (2007/10/02)
Sulphonyl- and acyl-hydrazones of 2-ethynylbenzaldehyde cyclise in the presence of base to give isoquinoline N-imines in moderate yield.The suggested mechanism involves primapy formation of the hydrazone anion followed by nucleophilic attack on the alkyne bond, either by anionic nitrogen to give an unstable 3H-2,3-benzodiazepine which rearranges to the isoquinoline N-imine, or by the neutral imine nitrogen to give the isoquinoline system directly.Attempts to extend the reaction to the semicarbazone and 2,4-dinitrophenylhydrazone were not successful.
