A new approach to morpholin-2-one derivatives via the reaction of β-amino alcohols with dicyanofumarates

Mlostoń, Grzegorz; Pieczonka, Adam M.; Ali, Korany A.; Linden, Anthony; Heimgartner, Heinz

doi:10.3998/ark.5550190.0013.314

Cited by 6 publications

(2 citation statements)

References 6 publications

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“…Hydrazines as powerful binucleophiles react easily with (E)-27 in ethanol at room temperature to furnish firstly similar derivatives 30. [34,35] The latest intermediates undergo intramolecular heterocyclization through a selective attack either onto ester (for unsubstituted hydrazine) or cyano group (for substituted hydrazines) leading to heterocycles 31 or 32, correspondingly (Scheme 12).…”

Section: Conjugate Nucleophilic Addition To β-Cyano Enoatesmentioning

confidence: 99%

“…When dialkyl dicyanofumarates 27 were treated with various 1,4‐binucleophiles such as diamines [36,37] or aminoalcohols, [34] the corresponding six‐membered heterocycles were obtained. For example, starting from trans ‐cyclohexane‐1,2‐diamine or aminoethanol, corresponding piperazin‐2‐ones 33 or morpholin‐2‐one 34 were isolated in good yield (Scheme 13).…”

Section: Aza‐michael Reaction With Pull‐pull Enoatesmentioning

confidence: 99%

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Pull‐Pull Alkenes in the Aza‐Michael Reaction

Rulev

Tyumentsev

2022

Adv Synth Catal

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Aza‐Michael addition is known to be one of the most exploited reactions in organic chemistry. Taking into account the fact that each seventh reaction in pharmaceutical industry involves the formation of at least one C−N bond, it is not surprising that this reaction is especially valuable for the synthesis of bioactive compounds and drugs. Traditionally, only push‐pull alkenes are regarded as starting material for this reaction. The participation of pull‐pull alkenes as Michael acceptors is much less studied. The presence of two vicinal electron‐withdrawing groups makes them highly reactive in nucleophilic reactions especially with nitrogen‐centered nucleophiles. This feature allows them to be excellent building blocks in the synthesis of bioactive molecules and polyfunctional materials. The review considers the most important and sometimes unexpected results obtained over the last two decades on the conjugate addition of nitrogen nucleophiles to pull‐pull alkenes bearing various acceptor moieties (alkoxycarbonyl‐, carbonyl‐, formyl‐, cyano‐, trifluoromethyl‐ or nitro group) in various combinations.

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Section: Conjugate Nucleophilic Addition To β-Cyano Enoatesmentioning

confidence: 99%

Section: Aza‐michael Reaction With Pull‐pull Enoatesmentioning

confidence: 99%

Pull‐Pull Alkenes in the Aza‐Michael Reaction

Rulev

Tyumentsev

2022

Adv Synth Catal

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Dialkyl Dicyanofumarates as Oxidizing Reagents for the Conversion of Thiols into Disulfides and Selenols into Diselenides

et al. 2017

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Aliphatic and aromatic thiols react smoothly with dialkyl dicyanofumarates in CH2Cl2 at room temperature to give the corresponding disulfides in excellent yields. Aliphatic 1,2‐, 1,3‐, and 1,4‐dithiols afford cyclic disulfides. Analogous reaction courses were observed for selenols, and the required diselenides also formed in nearly quantitative yields. In all of the reactions, dialkyl dicyanosuccinates formed as 1:1 mixtures of diastereoisomers as the only other product. Cysteamine (2‐mercaptoethylamine) behaved differently; the Michael addition of the primary amine group led to the complete consumption of the dicyanofumarate, and the formation of the disulfide containing an enamine moiety occurred without the formation of dicyanosuccinate.

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Unexpected Reaction Course of 3‐Amino‐5‐aryl‐1H‐pyrazoles with Dialkyl Dicyanofumarates

Ali

Ragab

Mlostoń

et al. 2013

Helvetica Chimica Acta

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On treatment of 3-amino-5-aryl-1H-pyrazoles 1 with dialkyl dicyanofumarates (=(E)-but-2-enedioates) 4 in boiling 1,2-dichloroethane, two competitive reactions occurred leading to 3-aryl-5-cyano-6,7-dihydro-6-oxo-1H-pyrazolo [3,4-b]pyridine-4-carboxylates 10 and 7-amino-2-arylpyrazolo[1,5-a]pyrimidine-5,6-dicarboxylates 11. In DMF at room temperature, as well as at 100°, only compounds 10 were isolated. The formation of the major products of type 10 was rationalized via Michael addition of 1 as a C(4)-nucleophile onto 4, followed by HCN elimination and lactamization. On the other hand, the minor products 11 result from a Michael addition of 1 onto 4 via the NH2 group, and subsequent HCN elimination and cyclization. The structures of the products have been established by X-ray crystallography.

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A new approach to morpholin-2-one derivatives via the reaction of β-amino alcohols with dicyanofumarates

Cited by 6 publications

References 6 publications

Pull‐Pull Alkenes in the Aza‐Michael Reaction

Pull‐Pull Alkenes in the Aza‐Michael Reaction

Dialkyl Dicyanofumarates as Oxidizing Reagents for the Conversion of Thiols into Disulfides and Selenols into Diselenides

Unexpected Reaction Course of 3‐Amino‐5‐aryl‐1H‐pyrazoles with Dialkyl Dicyanofumarates

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