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

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
3, 3
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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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
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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