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.
Highlights
During the last decade we have been involved in a program aimed at exploring the synthetic potentials of enaminones [1] as building blocks for polyfunctionally substituted aromatics and heteroaromatics [1,2,3]
2,4-diamino-5-benzoylisophthalonitrile, with molecular formula C15H10N4O and molecular mass M+ = 262, we found, that enaminone 1c and compound 2 react in acetic acid in the presence of
1a–d and 2 in Scheme 1 as secondary carbamides, but their tautomers having a hydrogen atom bound to N-1 or to the oxygen atom have to be considered as well
Summary
During the last decade we have been involved in a program aimed at exploring the synthetic potentials of enaminones [1] as building blocks for polyfunctionally substituted aromatics and heteroaromatics [1,2,3]. We have in the past successfully developed syntheses of polysubstituted benzenes [4,5] and polysubstituted pyridines [6,7] utilizing enaminones 1a–d as starting materials. In the present article we report our further results in this area where a novel one pot synthesis of 7-amino5-oxo-5,6-dihydro-1,6-naphthyridine-8-carbonitriles 9a–d, 2-aminopyrano[4,3,2-de][1,6]naphthyridine-3-carbonitrile derivatives 20a–c,e and (4-cyano-5-dicyanomethylene-2-oxo-2,5-dihydro-1Hpyrrol-3-yl)-acetic acid ethyl ester 15B could be achieved. To our knowledge only one derivative of the 2-aminopyrano[4,3,2-de][1,6]naphthyridine-3-carbonitrile system has been reported, prepared via a multistep route [8]. The newly synthesized 2-aminopyrano[4,3,2-de][1,6]naphthyridine-3-carbonitrile derivatives 20a–c,e seem interesting for biological activity investigations as investigations on such polynuclear aromatics are rare [8]
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