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Current Organic Synthesis
ISSN (Print): 1570-1794
ISSN (Online): 1875-6271
Epub Full Text Article
DOI: 10.2174/1570179411310010002      Price:  $95

Studies with Polyfunctional Hetero Aromatics and Aromatics: Synthesis of Tetraand Penta-Substituted Benzoic and Phthalic Acid Derivatives Through Reactions of Acetylenic Esters or Diesters with Arylidenemalononitriles in the Presence of LProline or DABCO

Author(s): Saleh M. Al-Mousawi, Moustafa Sherief Moustafa, Noha Mohamed Hilmy and Mohamed Hilmy Elnagdi
Reaction of ethyl propiolate with benzylidenemalononitrile 1a in the presence of L-proline was observed to produce the pyran derivative 7 in 80% yield. In contrast, diethyl acetylenedicarboxylate (6b) does not react with 1a in presence of L-proline. However when DABCO is used as the amine nucleophile, 6b reacts with 1a to form diethyl 5-amino-4,6-dicyano-3-phenyl-2,3-phthalate (20a). The structures of 7 and 20a were assigned by using X-ray crystallographic analysis. 2-aminoprop-1-ene-1,1,3-tricarbonitrile (28) reacts with diethyl acetylenedicarboxylate (6b) to yield (4-Cyano-5-dicyanomethyl-2-oxo-1,2-dihydro-pyrrol-3-ylidene)-acetic acid ethyl ester (31) whose structure was confirmed by X-Ray crystal structure.
DABCO, Ethyl propiolate, L-Proline, Diethyl acetylenedicarboxylate, Benzylidenemalononitrile, 2-Aminoprop-1-ene-1, 1, 3- tricarbonitrile.
Department of Chemistry, Faculty of Science; University of Kuwait: Safat; 13060: Kuwait, P.O. Box 5969, Kuwait.