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Synthesis and Reactivity of 2‐(6,7‐Diethoxy‐3,4‐dihydroisoquinolin‐ 1‐yl)acetonitrile towards Hydrazonoyl Halides
Author(s) -
Awad Enas M.,
Elwan Nehal M.,
Hassaneen Hamdi M.,
Linden Anthony,
Heimgartner Heinz
Publication year - 2001
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(20010516)84:5<1172::aid-hlca1172>3.0.co;2-x
Subject(s) - chemistry , isoquinoline , acetonitrile , halide , tautomer , ring (chemistry) , medicinal chemistry , closure (psychology) , amide , reactivity (psychology) , organic chemistry , medicine , alternative medicine , pathology , economics , market economy
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 Et 3 N 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.