☆ 4.6 Article

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

MOLECULES (2013)

Journal

MOLECULES

Volume 18, Issue 1, Pages 276-286

Publisher

MDPI AG

DOI: 10.3390/molecules18010276

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

Categories

Biochemistry & Molecular Biology Chemistry, Multidisciplinary

Funding

Kuwait University Research Administration [SC01/10]
SAF [GS 03/08, GS 01/01, GS 01/03, GS 01/05]

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Abstract

Reaction of enaminones 1a-d 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 9a-d. On the other hand, 2-aminopyrano[4,3,2-de][1,6]naphthyridine-3-carbonitriles 20a-c,e were the only obtained products from the reactions of 1a-d 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.

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