Page 39 - Book of Abstracts 2020
P. 39
th
8 Biannual Conference on Chemistry - CHEM 08
Synthesis of New Heterocyclic Compounds via
Isoquinoline-1-acetonitrile
Fatma M. Saleh, Yara N. Laboud*, Hyam A. Abdelhadi, Mohamed A.
Mohamed Teleb
Department of Chemistry, Faculty of Science, Cairo University. Email:
yaranour333@gmail.com
ABSTRACT
Refluxing of 2-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)acetonitrile 1 with
ethyl α-cyanocinnamates 2 in acetonitrile in the presence of piperidine gave the
corresponding 2-aryl-9,10-dimethoxy-4-oxo-6,7-dihydro-4H-pyrido[2,1-
a]isoquinoline-1,3-dicarbonitrile 3. The reaction of enaminone 4 (prepared by
treatment of 2-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)acetonitrile 1 with
DMF-DMA in refluxing dioxane) with aryl acetonitrile 5 in refluxing acetonitrile
in the presence of piperidine afforded 3-aryl-4-imino-9,10-dimethoxy-6,7-
dihydro-4H-pyrido[2,1-a]isoquinoline-1-carbonitrile 6. Treatment of 2-(6,7-
dimethoxy-3,4-dihydroisoquinolin-1-yl)acetonitrile 1 with aryl aldehyde 7 in
absolute alcohol at room temperature in the presence of concentrated
hydrochloric acid yielded 3-aryl-2-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-
yl)acrylonitrile 8. All the new synthesized compounds were identified by
elemental analysis and spectral data.
Keywords: Isoquinoline-1-acetonitrile, α-Cyanocinnamates, 4H-Pyrido[2,1-
a]isoquinoline, 4-imino-4H-pyrido[2,1-a]isoquinoline, Enaminone and
Knoevenagel condensation.
BOOK OF ABSTRACTS CHEM 08 (2020) Page 38
