Synthesis of Heterocycles from Alkyl 3-(Dimethylamino)propenoates and Related Enaminones

Stanovnik, B.; Svete, Jurij

doi:10.1021/cr020093y

Cited by 489 publications

(212 citation statements)

References 160 publications

(454 reference statements)

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“…Indeed, the configuration of the double bond of α,β-unsaturated carbonyl compounds can be determined on the basis of this long range 3 J ( 1 H, 13 C O) heteronuclear coupling constant. The 3 J(H,C) of 1 H and 13 C O nuclei with a cis orientation with respect to the double bond are usually smaller (2-6 Hz) than those with a trans orientation (8-12 Hz) [16]. In our case, the 3 J(H,C) value of 4 Hz indicated a cis orientation of 1 H and 13 C nuclei corresponding to the E configuration of the exocyclic double bond.…”

Section: Chemistrymentioning

confidence: 39%

Synthesis and biological evaluation of diversely substituted indolin-2-ones

Bouchikhi

Rossignol

Sancelme

et al. 2008

European Journal of Medicinal Chemistry

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The synthesis of indolin-2-one derivatives substituted in the 3-position by an aminomethylene group bearing either an ornithine or a lysine residue is described. The inhibitory activities of these compounds toward a panel of eight kinases were examined. Furthermore, the antibacterial activities of the prepared compounds were tested against two Gram-positive bacteria Bacillus cereus and Streptomyces chartreusis, a Gram-negative bacterium Escherichia coli and a yeast Candida albicans.

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Section: Chemistrymentioning

confidence: 39%

Synthesis and biological evaluation of diversely substituted indolin-2-ones

Bouchikhi

Rossignol

Sancelme

et al. 2008

European Journal of Medicinal Chemistry

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“…The wide applicability of 3-(dimethylamino)-propenoates and related enaminones as versatile reagents in heterocyclic synthesis, 21 parallel solution-phase and solid-phase synthesis of fused pyrimidinones, 22 and stereochemical synthesis, 23 including natural products and their analogues, e.g. the aplysinopsins, 24 meridianines, 25 dipodazines, 26 and triprostatines 27 has been demonstrated.…”

Section: Figure 1 5-methyl-4-[4-(methylthio)benzoyl]-1h-imidazol-2(3mentioning

confidence: 99%

A simple synthesis of 4-aroyl-5-methyl-1H-imidazol-2(3H)-one derivatives (Enoxymone analogues) from aryl methyl ketones via enaminones

Bezenšek¹,

Grošelj²,

Stare³

et al. 2013

Arkivoc

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Dedicated to Professor Rosa M. Claramunt on the occasion of her 65th anniversary AbstractAryl methyl ketones 1a-e gave with N,N-dimethylacetamide dimethylacetal (DMADMA) (E)-1-aryl-3-(dimethylamino)-but-2-en-1-ones 2a-e. Substitution of the N,N-(dimethylamino) group in the reaction with ammonium acetate afforded the corresponding (Z)-3-amino-1-aryl-but-2-en-1-ones 3a-e. In the reaction of 3a-e with diethyl azodicarboxylate intermediates 4a-e were formed, which were, in most cases without isolation, cyclized into ethyl (5-aroyl-4-methyl-2-oxo-2,3-dihydro-1H-imidazol-1-yl)carbamates 5a-e. Hydrolysis of the ester group, followed by the decarboxylation and deamination of intermediates 6a-c,e produced 4-aroyl-5-methyl-1H-imidazol-2(3H)-ones 7a-c,e.

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“…Ever since, enaminones and related compounds (enaminoesters, enaminonitriles,…) have become very useful synthons in organic synthesis. [2][3][4][5][6][7][8] A privileged status among them have cyclic enaminones and their derivatives. 9,10 They can, in principle, be divided into three structural types I-III (Fig.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of [1,2-a]-fused tricyclic dihydroquinolines by palladium-catalyzed intramolecular C–N cross-coupling of polarized heterocyclic enamines

Brož¹,

Růžičková²,

Šimůnek³

2016

Arkivoc

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A simple methodology for [1,2-a]-fused tricyclic dihydroquinolines is established. The key step of the methodology is an intramolecular Buchwald-Hartwig amination reaction of suitable halogenated (both bromo and chloro) cyclic enaminoketones, enaminoesters and enaminonitriles with various ring size (from five-to seven-membered). Optimal reaction conditions (palladium source, base, ligand) depend on the ring size of the starting enamine, giving 65-98% yield of the tricyclic product. A treatment of the products with perchloric acid gives respective quinolinium perchlorates.

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Synthesis of Heterocycles from Alkyl 3-(Dimethylamino)propenoates and Related Enaminones

Cited by 489 publications

References 160 publications

Synthesis and biological evaluation of diversely substituted indolin-2-ones

Synthesis and biological evaluation of diversely substituted indolin-2-ones

A simple synthesis of 4-aroyl-5-methyl-1H-imidazol-2(3H)-one derivatives (Enoxymone analogues) from aryl methyl ketones via enaminones

Synthesis of [1,2-a]-fused tricyclic dihydroquinolines by palladium-catalyzed intramolecular C–N cross-coupling of polarized heterocyclic enamines

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