354153-71-2Relevant academic research and scientific papers
Synthesis and reactivity of 2-(6,7-diethoxy-3,4-dihydroisoquinolin-1-yl)acetonitrile towards hydrazonoyl halides
Awad, Enas M.,Elwan, Nehal M.,Hassaneen, Hamdi M.,Linden, Anthony,Heimgartner, Heinz
, p. 1172 - 1180 (2007/10/03)
The synthesis of 2-(6,7-diethoxy-3,4-dihydroisoquinolin-1-yl)acetonitrile (1) has been performed by ring closure of the corresponding amide according to the Bischler-Napieralski method (Scheme 1). Based on spectroscopic data, the tautomeric 2-(tetrahydroisoquinolin-1-ylidene)acetonitrile is the actual compound. The reactions of 1 with α-oxohydrazonoyl halides 4 in the presence of Et3N led to 2-(aryldiazenyl)pyrrolo[2,1-a]-isoquinoline derivatives 8 (Scheme 2), whereas with C-(ethoxycarbonyl)hydrazonoyl chlorides 14, 2-(arylhydrazono)pyrrolo[2,1-a]isoquinoline-1-carbonitriles 16 were formed (Scheme 4). The structures of the products were established from their analytical and spectroscopic data and, in the case of 8b, by X-ray crystallography.
