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Molecules 2013, 18(1), 276-286; doi:10.3390/molecules18010276
Article

Unexpected Behavior of Enaminones: Interesting New Routes to 1,6-Naphthyridines, 2-Oxopyrrolidines and Pyrano[4,3,2-de][1,6]naphthyridines

1,* , 1,* , 2
,
1
,
3, 3
 and
1
1 Department of Chemistry, Faculty of Science, University of Kuwait, P.O. Box 5969, Safat 13060, Kuwait 2 Women Students-Medical Studies & Sciences Sections, Department of Chemistry, College of Science, King Saud University, Riyadh, KSA, P.O. Box 22452, Riyadh 11495, Saudi Arabia 3 Johannes Gutenberg — Universität Mainz, Institute of Organic Chemistry, Mainz, Germany
* Authors to whom correspondence should be addressed.
Received: 16 October 2012 / Revised: 22 October 2012 / Accepted: 26 November 2012 / Published: 27 December 2012
(This article belongs to the Section Organic Synthesis)
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Abstract

Reaction of enaminones 1ad with 2-aminoprop-1-ene-1,1,3-tricarbonitrile (2) in the presence of AcOH/NH4OAc afforded 7-amino-5-oxo-5,6-dihydro-1,6-naphthyridine-8-carbonitrile derivatives 9ad. On the other hand, 2-aminopyrano[4,3,2-de] [1,6]naphthyridine-3-carbonitriles 20ac,e were the only obtained products from the reactions of 1ad with 2 in the presence of AcOH/NaOAc, while 1d afforded [3,5-bis-(4-chloro-benzoyl)-phenyl]-(4-chloro-phenyl)-methanone 21 under the same condition. The reaction of 2 with diethyl acetylenedicarboxylate in the presence of AcOH/NH4OAc afforded (4-cyano-5-dicyanomethylene-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)-acetic acid ethyl ester 15B.
Keywords: enaminones; 3-amino-2-cyanopent-2-enedinitrile; 7-amino-5-oxo-5,6-dihydro-1,6-naphthyridine-8-carbonitrile; 2-aminoprop-1-ene-1,1,3-tricarbonitrile enaminones; 3-amino-2-cyanopent-2-enedinitrile; 7-amino-5-oxo-5,6-dihydro-1,6-naphthyridine-8-carbonitrile; 2-aminoprop-1-ene-1,1,3-tricarbonitrile
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Moustafa, M.S.; Al-Mousawi, S.M.; Hilmy, N.M.; Ibrahim, Y.A.; Liermann, J.C.; Meier, H.; Elnagdi, M.H. Unexpected Behavior of Enaminones: Interesting New Routes to 1,6-Naphthyridines, 2-Oxopyrrolidines and Pyrano[4,3,2-de][1,6]naphthyridines. Molecules 2013, 18, 276-286.

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