Heterocyclization of michael adducts of β-diketones with arylmethylidene derivatives of malononitrile dimers

Alekseeva, A. Yu.; Mikhailov, D. L.; Бардасов, И. Н.; Ершов, О. В.; Насакин, О. Е.; Lyshchikov, A. N.

doi:10.1134/s1070428014020171

Cited by 18 publications

(4 citation statements)

References 7 publications

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“…Cyanoacetohydrazide 1 [48] and 2-amino-4-arylbuta-1,3-diene-1,1,3-tricarbonitriles 11а-11d [49][50][51] were obtained according to the known methods.…”

Section: Doi: 101134/s1070363221110025mentioning

confidence: 99%

Methylene Components Exchange in the Reaction of Cyanoacetohydrazide with 2-Amino-4-arylbuta-1,3-diene-1,1,3-tricarbonitriles

et al. 2021

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“…Cyanoacetohydrazide 1 [48] and 2-amino-4-arylbuta-1,3-diene-1,1,3-tricarbonitriles 11а-11d [49][50][51] were obtained according to the known methods.…”

Section: Doi: 101134/s1070363221110025mentioning

confidence: 99%

Methylene Components Exchange in the Reaction of Cyanoacetohydrazide with 2-Amino-4-arylbuta-1,3-diene-1,1,3-tricarbonitriles

et al. 2021

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“…4‐Amino‐5‐aryl‐2‐methoxy‐6‐oxo‐5,6,7,8,9,10hexahydrobenzo[ b ][1,8]naphthyridine‐3‐carbonitriles 143 were synthesized by the reaction of aldehydes 1 and 2‐aminoprop‐1‐ene‐1,1,3‐tricarbonitrile 111 with 1,3‐cyclohexanediones 72 in methanol in the presence of sodium methylate as a catalyst (Scheme ) …”

Section: Synthesis Of Fused Tricyclic Systemmentioning

confidence: 99%

“…4-Amino-5-aryl-2-methoxy-6-oxo-5,6,7,8,9,10hexahydrobenzo[b] [1,8]naphthyridine-3-carbonitriles 143 were synthesized by the reaction of aldehydes 1 and 2-aminoprop-1-ene-1,1,3-tricarbonitrile 111 with 1, 3-cyclohexanediones 72 in methanol in the presence of sodium methylate as a catalyst (Scheme 80). [156] Bis(chromeno[2,3-b]pyridine) derivatives 145 and 146 were prepared by one-pot, three-component reaction of bisaldehydes with 2-aminoprop-1-ene-1, 1,3-tricarbonitrile 111 and dimedone 72 in ethanol in the presence of piperidine. The reactions were proceeded to give either the bis(4-amino-2,6-dioxo-hexahydro-2H-chromeno [2,3-b]pyridine-3-carbonitriles) 144 or bis(2,4-diamino-tetrahydro-5H-chromeno [2,3-b]pyridine-3-carbonitriles) 145 depending on the length and position of the spacer in the bisaldehyde derivatives (Scheme 81).…”

Section: Hexahydrobenzo[b][18] Naphthyridinesmentioning

confidence: 99%

Synthesis of heterocyclic compounds via Michael and Hantzsch reactions

Abdella

Abdelmoniem

Abdelhamid

et al. 2020

Journal of Heterocyclic Chem

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Heterocycles represent the largest diversity of organic compounds with signifcant chemical, biomedical, and industrial applications. They exist in numerous natural products, dyes, and as scaffolds in diverse drugs and related pharmaceutically active substances. Substantial attention has been paid to develop various elegant methods to synthesize heterocycles. Among different strategies, Michael and Hantzsch reactions are considered as effective approaches for construction of heterocycles and their corresponding fused derivatives. This review covers this area especially in the last 10 years. The heterocyclic systems reported in this review are classified according to the kind of the heterocyclic systems.

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“…Thus, the Michael adduct undergoes tandem cyclization, and the overall process may be regarded as Michael-Initiated Tandem Ring Closure (MITRC). Such transformations are typical of arylmethylidene derivatives 1 [20][21][22][23][24] MIRC REACTIONS OF 4-ARYL-2-AMINOBUTA-1,3-DIENE-1,1,3-TRICARBONITRILES.…”

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confidence: 99%

MIRC reactions of 4-aryl-2-aminobuta-1,3-diene-1,1,3-tricarbonitriles. Synthesis of 2-amino-6-aryl-5-cyano-4-(dicyanomethylidene)-3-azabicyclo[3.1.0]hex-2-ene-1-carboxylic acid esters and amides

et al. 2015

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4-Aryl-2-aminobuta-1,3-diene-1,1,3-tricarbonitriles (benzylidene derivatives of malononitrile dimer) reacted with bromo(cyano)acetic acid amide and esters to give the corresponding 2-amino-6-aryl-5cyano-4-(dicyanomethylidene)-3-azabicyclo[3.1.0]hex-2-ene-1-carboxylic acid amides and esters.1, Ar = Ph (a), 2-ClC 6 H 4 (b), 4-MeC 6 H 4 (c), 3,4,5-(MeO) 3 C 6 H 2 (d); 2, X = NH 2 , Ar = Ph (a), 2-ClC 6 H 4 (b), 4-MeC 6 H 4 (c); X = MeO, Ar = Ph (d), 2-ClC 6 H 4 (e); Ar = 3,4,5-(MeO) 3 C 6 H 2 , X = EtO (f).

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Heterocyclization of michael adducts of β-diketones with arylmethylidene derivatives of malononitrile dimers

Cited by 18 publications

References 7 publications

Methylene Components Exchange in the Reaction of Cyanoacetohydrazide with 2-Amino-4-arylbuta-1,3-diene-1,1,3-tricarbonitriles

Methylene Components Exchange in the Reaction of Cyanoacetohydrazide with 2-Amino-4-arylbuta-1,3-diene-1,1,3-tricarbonitriles

Synthesis of heterocyclic compounds via Michael and Hantzsch reactions

MIRC reactions of 4-aryl-2-aminobuta-1,3-diene-1,1,3-tricarbonitriles. Synthesis of 2-amino-6-aryl-5-cyano-4-(dicyanomethylidene)-3-azabicyclo[3.1.0]hex-2-ene-1-carboxylic acid esters and amides

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