Publication: Synthesis and Reactivity of 2-(6,7-Diethoxy-3,4-dihydroisoquinolin-1-yl)acetonitrile towards Hydrazonoyl Halides
Synthesis and Reactivity of 2-(6,7-Diethoxy-3,4-dihydroisoquinolin-1-yl)acetonitrile towards Hydrazonoyl Halides
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Awad, E. M., Elwan, N. M., Hassaneen, H. M., Linden, A., & Heimgartner, H. (2001). Synthesis and Reactivity of 2-(6,7-Diethoxy-3,4-dihydroisoquinolin-1-yl)acetonitrile towards Hydrazonoyl Halides. Helvetica Chimica Acta, 84(5), 1172–1180. https://doi.org/10.1002/1522-2675(20010516)84:5<1172::AID-HLCA1172>3.0.CO;2-X
Abstract
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Abstract
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 alpha-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-(arylhydrazon
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- Awad, Enas M
- Elwan, Nehal M
- Hassaneen, Hamdi M
- Heimgartner, Heinz
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Awad, E. M., Elwan, N. M., Hassaneen, H. M., Linden, A., & Heimgartner, H. (2001). Synthesis and Reactivity of 2-(6,7-Diethoxy-3,4-dihydroisoquinolin-1-yl)acetonitrile towards Hydrazonoyl Halides. Helvetica Chimica Acta, 84(5), 1172–1180. https://doi.org/10.1002/1522-2675(20010516)84:5<1172::AID-HLCA1172>3.0.CO;2-X
