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Synthesis 2006(1): 59-62  
DOI: 10.1055/s-2005-921750
PAPER
© Georg Thieme Verlag Stuttgart · New York

Studies with Functionally Substituted Enamines: The Reactivity of Enaminals and Enamino Esters toward Naphthoquinone, Hydrazonoyl Halides, Aminoazoles and Hippuric Acid

Balkis AL-Saleha, Saad Makhseed*a, Huwaida M. E. Hassaneenb, Mohamed Hilmy Elnagdib
a Chemistry Department, Faculty of Science, University of Kuwait, P. O. Box 5969, Safat 13060, Kuwait
e-Mail: smakhseed@kuc01.kuniv.edu.kw;
b Chemistry Department, Faculty of Science, Cairo University, Giza 12136, A. R. Egypt
e-Mail: shelmy@access.com.eg;
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Publication History

Received 18 May 2005
Publication Date:
16 December 2005 (online)

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Abstract

Whereas enamines 1a,b react with naphthoquinone (2) to yield the naphthofuranals 5a,b, enamine ester 1c react with 2 to yield benzoindole derivatives 7. Enamine 1b reacts with hydrazonoyl halides 8 to yield 3,4-disubstituted pyrazoles 12. On the other hand, the enaminal 1a failed to react with 8, while enamine ester 1c afforded hydrazone 16 on treatment with 8. The enamino ester 1b afforded triethyl 1,3,5-benzenetricarboxylates on refluxing in acetic acid.

Key words

enaminals - enamino esters - hydrazonoyl halides - aminoazoles - enaminonitriles