3-Amino-5,5-dimethylcyclohex-2-enone in the synthesis of heterocyclic compounds (review)

Rudenko, D. A.; Шуров, С. Н.; Stepanyan, Yu. G.

doi:10.1007/s10593-011-0818-9

Cited by 5 publications

(2 citation statements)

References 49 publications

(56 reference statements)

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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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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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“…[1]), searching for new heterocyclic systems or novel methods for the synthesis of the existing ones represents a very important part of organic chemistry. Enaminones, due to their ability to react with both electrophiles and nucleophiles, are versatile synthons, and not only in heterocyclic chemistry (for many reviews see, e.g., [2–6]). During the past several years we have dealt with the reaction of various enaminones with diazonium salts and established a number of methods for the construction of some important or unusual heterocyclic systems [7–15], including a simple protocol leading from enaminones 1 to 6-substituted 4-amino-5-aryldiazenyl-1-arylpyridazinium salts 2 [14–15].…”

Section: Introductionmentioning

confidence: 99%

A simple, enaminone-based approach to some bicyclic pyridazinium tetrafluoroborates

Josefík¹,

Svobodová²,

Bertolasi³

et al. 2013

Beilstein J. Org. Chem.

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SummaryEasily obtainable cyclic enaminones (piperidin-2-ylidenealkanones) can be transformed into substituted bicyclic pyridazinium tetrafluoroborates upon treatment with corresponding diazonium salts. The transformation can be performed either in a one-pot way or in a two-step process with the isolation of single azo-coupled enaminone as the intermediate. The former method is superior. Under the optimized conditions, a number of pyridazinium salts substituted with both electron-donating and electron-withdrawing substituents was easily synthesized. A mechanism of the formation of the pyridazinium salts is suggested. A partial drawback is the possibility of the formation of a mixture of products when using a different diazonium salt in each step due to a reversibility of the azo coupling. This can be suppressed by using a more reactive diazonium salt before a less reactive one.

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ChemInform Abstract: 3‐Amino‐5,5‐dimethylcyclohex‐2‐enone in the Synthesis of Heterocyclic Compounds

2012

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3-Amino-5,5-dimethylcyclohex-2-enone in the synthesis of heterocyclic compounds (review)

Cited by 5 publications

References 49 publications

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

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

A simple, enaminone-based approach to some bicyclic pyridazinium tetrafluoroborates

ChemInform Abstract: 3‐Amino‐5,5‐dimethylcyclohex‐2‐enone in the Synthesis of Heterocyclic Compounds

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