Reactions of 1,5-Diketones with Ammonia and Its Derivatives. (Review)

Харченко, В. Г.; Маркова, Л. И.; Федотова, О. В.; Пчелинцева, Н. В.

doi:10.1023/b:cohc.0000008257.42400.9e

Cited by 40 publications

(13 citation statements)

References 15 publications

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“…Formation of carbon−carbon bonds using commercially available feedstocks is a highly desirable goal in organic synthesis. 1 Over the last few decades, significant efforts have been made to develop environmentally benign acceptorless dehydrogenation of inexpensive substrates such as alcohols without having to use stoichiometric quantities of the oxidant. 2 Alcohols can be transformed into the corresponding carbonyl compounds using different metal complexes; the in situ formed carbonyl compounds can lead to successive reaction in the same pot to generate compounds with new functionalities.…”

Section: ■ Introductionmentioning

confidence: 99%

Cobalt(II)porphyrin-Mediated Selective Synthesis of 1,5-Diketones via an Interrupted-Borrowing Hydrogen Strategy Using Methanol as a C1 Source

et al. 2021

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A novel cobalt(II)porphyrin-mediated acceptorless dehydrogenation of methanol is reported for the first time. This methodology has been applied for the coupling of a variety of ketones with methanol to produce 1,5-diketones along with H2 and H2O as the environment friendly byproducts. This paradigm was also demonstrated for a one-pot synthesis of substituted pyridines using a sequential addition protocol where the 1,5-diketones were generated in situ. From many experiments including those involving deuterium labeling, it is proposed that protonated cobalt(II)porphyrin methoxide complex acts as an intermediate to generate formaldehyde along with a metal hydride.

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Section: ■ Introductionmentioning

confidence: 99%

Cobalt(II)porphyrin-Mediated Selective Synthesis of 1,5-Diketones via an Interrupted-Borrowing Hydrogen Strategy Using Methanol as a C1 Source

et al. 2021

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“…That is caused by an electron density pulling away from the C=C bond, that makes it more attractive for anion attack. The presence of electron-donating substituents in the ring Ar 2 at the carbonyl group in enynones 1a,c,i,l does not significantly decrease the yields of the target diketones 2.1a,c,i,l/2.2a,c,i,l (entries 4,5,11,14). However, it may take a longer reaction time (entries 11,14).…”

Section: Entrymentioning

confidence: 96%

“…The obtained reaction products contain δ-diketones structural fragment. In general, terminally arylated δ-diketones have been widely applied for synthesis of various heterocyclic compounds (Scheme 1) [5][6][7][8][9][10]. Substituted 1,2-diazepines were obtained by interaction of such diketones with hydrazine [5].…”

Section: Introductionmentioning

confidence: 99%

“…In general, terminally arylated δ-diketones have been widely applied for synthesis of various heterocyclic compounds (Scheme 1) [5][6][7][8][9][10]. Substituted 1,2-diazepines were obtained by interaction of such diketones with hydrazine [5]. These diketones were cyclized into tetrahydropyrans in the reaction with indium chloride (III) and triethylsilane [6].…”

Section: Introductionmentioning

confidence: 99%

“…Scheme 1. Reactions of δ-diketones leading to various heterocycles and cyclopropanes: a-N2H4, HCl, EtOH, reflux [5]; b-InCl3 or Al(OTf)3, Et3SiH,CH3CN, r.t. [6]; c-BF3×Et2O, PhMe, 130 °C [7,8]; d-NaOH, I2, 25-40 °C [9]; e-Ni(dppe)Cl2, ZnCl2, B(OH)2Ar, THF, 100 °C [10].…”

Section: Introductionmentioning

confidence: 99%

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Michael Addition of 3-Oxo-3-phenylpropanenitrile to Linear Conjugated Enynones: Approach to Polyfunctional δ-Diketones as Precursors for Heterocycle Synthesis

2022

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Reaction of linear conjugated enynones, 1,5-diarylpent-2-en-4-yn-1-ones [Ar1C≡CCH=CHC(=O)Ar2], with 3-oxo-3-phenylpropanenitrile (NCCH2COPh) in the presence of sodium methoxide MeONa as a base in MeOH at room temperature for 4–26 h affords polyfunctional δ-diketones as a product of regioselective Michael addition to the double carbon–carbon bond of starting enynones. The δ-diketones have been formed as mixtures of two diastereomers in a ratio of 2.5:1 in good general yields of 53–98%. A synthetic potential of the obtained δ-diketones has been demonstrated by heterocyclization with hydrazine into substututed 5,6-dihydro-4H-1,2-diazepine.

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Synthesis of Poly‐Substituted Pyridines via Noble‐Metal‐Free Cycloaddition of Ketones and Imines

Mao

Hong

et al. 2021

Chemistry An Asian Journal

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An eco-friendly and noble-metal-free formal [4 + 2] cycloaddition reaction was developed for the efficient synthesis of biologically interesting poly-substituted pyridines from easily available ketones and imines, whereby two sequential CÀ C bonds are formed. The given approach features a unique synthetic strategy of imines and ketones with wide substrate scope, good functional group tolerance, mild conditions and operational simplicity, which represents a more direct pathway to synthesize polysubstituted pyridines than traditional methods.

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Reactions of 1,5-Diketones with Ammonia and Its Derivatives. (Review)

Cited by 40 publications

References 15 publications

Cobalt(II)porphyrin-Mediated Selective Synthesis of 1,5-Diketones via an Interrupted-Borrowing Hydrogen Strategy Using Methanol as a C1 Source

Cobalt(II)porphyrin-Mediated Selective Synthesis of 1,5-Diketones via an Interrupted-Borrowing Hydrogen Strategy Using Methanol as a C1 Source

Michael Addition of 3-Oxo-3-phenylpropanenitrile to Linear Conjugated Enynones: Approach to Polyfunctional δ-Diketones as Precursors for Heterocycle Synthesis

Synthesis of Poly‐Substituted Pyridines via Noble‐Metal‐Free Cycloaddition of Ketones and Imines

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