Diethyl N,N‐dimethylaminomethylenemalonate in the synthesis of fused heterocyclic systems

doi:10.1002/JHET.5570330407

Paper

Diethyl N,N‐dimethylaminomethylenemalonate in the synthesis of fused heterocyclic systems

Published Jul 1, 1996 · Mihael Kušar, J. Svete, B. Stanovnik

Journal of Heterocyclic Chemistry

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17

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Abstract

The reactions of diethyl N,N-dimethylaminomethylenemalonate (3) with N- and C- nucleophiles were studied. In the reaction of 3 with heterocyclic amines 4, with the amino group attached at α-position in respect to the ring nitrogen atom, substitution of the dimethylamino group in 3 with the heterocyclic amino took place to give diethyl heteroarylaminomethylenemalonates 5, which can cyclize into fused azino- 6 or azolopyrimidinones 7. In the reaction of 3 with the compound with an active methylene group attached at α-position in regard to the ring nitrogen atom, such as pyridinylacetonitrile (8), ethyl pyridinyl- (9), and quinolinylacetate (10), fused quinolizines 11 and 12, and benzo[c]quinolizine 13 were formed, respectively. Heterocyclic systems with an active or potentially active methylene group incorporated in the ring system, such as pyrazole 14, pyrimidine 15, and pyridine derivative 18, gave with 3 fused pyranones 16, 17, and 19, and dihydroxynaphthalenes 22 and 23 naphtho[2,1-b]pyranones 24 and 25.

Study Snapshot

Diethyl N,N-dimethylaminomethylenemalonate can be used to synthesize fused heterocyclic systems with various methylene groups, such as pyrazole, pyrimidine, and pyridine derivatives.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Diethyl N,N‐dimethylaminomethylenemalonate in the synthesis of fused heterocyclic systems

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