The Reaction of Enaminones with Carboxamidines: A Convenient Route for the Synthesis of Polyaza Heterocycles

Bejan, Elena; Haddou, H. Aït; Daran, Jean‐Claude; Balavoine, G.

doi:10.1055/s-1996-4330

Cited by 75 publications

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“…The reaction of enamino-oxoquinoline 140 with amidines such as guanidine and formamidine occurred readly under basic conditions leading to pyrimidine 1 4 2 in high yields. One of the most important characteristics in the reactivities of the enaminones is the displacement of the N,N-dimethylamino groups by different nucleophiles [101]. One probable mechanism might be the attack of the amidine on β-carbon atom of enaminone to give 1 4 1, which on subsequent intramolecular cyclisation followed by elimination of water yielded pyrimidine 142 (Figure 52) [101].…”

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confidence: 99%

Recent development in preparation reactivity and biological activity of enaminoketones and enaminothiones and their utilization to prepare heterocyclic compounds

Negri

Kascheres

2004

Journal of Heterocyclic Chem

176

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Enaminoketones and esters are gaining increased interest, particularly cyclic-β-enaminoesters, which are known as important intermediates for the synthesis of heterocycles and natural products, because the enantioselective preparation of highly functionalized compounds is of central importance in synthetic chemistry. Enaminones are versatile synthetic intermediates that combine the ambident nucleophilicity of enamines with the ambident eletrophilicity of enones. Enaminoketones and enaminonitriles have proven to be versatile building blocks for the synthesis of various heterocycles such as pyridine, pyrimidine and pyrrole derivatives. Enaminones systems have "enone" character, and may act as acceptors in both 1,2 and 1,4-additions. In this way the enaminone serves as a scaffold for annulation, and can gain access to systems such as pyrroles indolizidines, quinolizidines and perhydroindoles, all of which are common motifs in alkaloid structures. Enaminones are frequently employed as building blocks for the preparation of a variety of bicyclic compounds of biological interest and have been recently recognized as potential anticonvulsant compounds. Since a large number of developments in the use of enaminones in heterocyclic synthesis have occurred, a review of the recent developments in the synthetic approaches, covering the literature since 1995 until 2004, to these interesting molecules and their useful chemical transformations and biological activity can be considered of considerable value.J. Heterocyclic Chem., 41, 461 (2004).Enaminoketones. Introduction.The term enaminone was introduced by Greenhill to define the enamine of a 1,3-diketone, β-ketoester or similar 1,3-difunctional reagents, and is used to indicate any compound containing the conjugated system N-C=C-C=O [1]. Enaminones are versatile synthetic intermediates that combine the ambident nucleophilicity of enamines with the ambident eletrophilicity of enones. The chemistry of the enaminocarbonyl group 1 is potentially an area of considerable scope when one considers that there are present in this moiety, three nucleophilic sites (a, c and e) and two electrophilic sites (b and d) [2][3][4] (Figure 1).Theorically, primary and secondary acyclic enaminones can exist in three tautomeric forms: ketamino form, iminoenol form and oxoimino form [1][2][3]. There is also evidence that cyclic enaminones exist primarily in the enaminoketo form. A study of cyclic enaminoketones shows that these compounds have a significant steric fator in the six-membered ring. The six-membered ring enaminoketones are only slightly stronger bases than the saturated amines, whereas five-and-seven membered rings are much stronger bases than saturated amines. This has been attributed to a large steric strain present in six-membered enaminoketones [5].β-Aminoenones or enaminoketones can exist in four conformations owing to restricted rotations around the C=C double and C-C=O single bonds [3]. Enaminones with primary or secondary amino groups can exist in both Z-and E-forms. If there is a...

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confidence: 99%

Recent development in preparation reactivity and biological activity of enaminoketones and enaminothiones and their utilization to prepare heterocyclic compounds

Negri

Kascheres

2004

Journal of Heterocyclic Chem

176

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“…The dark brown solution obtained was evaporated to dryness. The resulting darkbrown crystalline material was washed with hexane (3 ϫ 100 mL) and with diethyl ether (3 ϫ100 mL), yielding 10.6 g (yield 73 %) of pure, bright yellow 3a, as previously obtained by Balavoine et al [45] Synthesis of 3- (Dimethylamino)-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one (3b): [46] 3b was synthesized using the procedure described above for the preparation of 3a, starting from 5 g (0.0269 mol) of 2-acetyl-1-naphthol. 3b was obtained as a pure yellow powder, [46] with a yield of 75 % (4.9 g).…”

Section: Syntheses Of the Ligandsmentioning

confidence: 89%

“…Chem. 2007, 4197-4206 1-(pyridin-2-yl)prop-2-en-1-one (3a): [45] 10 g (0.0825 mol) of 2-acetylpyridine (1a) were introduced in a round-bottomed flask. Then, 20 mL (17.9 g, 0.1504 mol) of N,N-dimethylformamide dimethyl acetal (2) were added, and the resulting reaction mixture was refluxed overnight.…”

Section: Syntheses Of the Ligandsmentioning

confidence: 99%

Pyrazole‐Based Ligands for the [Copper–TEMPO]‐Mediated Oxidation of Benzyl Alcohol to Benzaldehyde and Structures of the Cu Coordination Compounds

et al. 2007

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New pyrazole‐based ligands have been designed, and the catalytic performances of their copper(II) complexes for the [copper/TEMPO]‐mediated oxidation of benzyl alcohol to benzaldehyde have been examined. The pyridine‐pyrazole ligands give efficient catalysts, while the use of naphthol‐pyrazole ligands results in inactive catalytic systems. Single‐crystals of four Cu coordination compounds obtained from pyridine‐pyrazole ligands and a free ligand have been isolated and were characterized by X‐ray diffraction. Thus, the solid‐state structures of three copper(II) complexes are described, together with a copper(I) coordination chain, exhibiting luminescent properties. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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“…After 2 hrs, NH 4 OAc (8g, excess) was added and the suspension heated at 100°C for 2 hrs. During this time, the colour of the mixture changed from red to brown, and accompanied by formation of a fine brown precipitate of the product [20][21][22][23][24][25][26][27][28][29][30] . Water (50 ml) was added and the pasty precipitate of 2-(6-pyridin-2-yl)-4-ptolylpyridin-2yl) pyridine isolated, washed with water (50 ml) and cold EtOH (50 ml).…”

Section: Methodsmentioning

confidence: 99%

SYNTHESIS AND CHARACTERIZATION OF BISMERCAPTO (2, 2′:6′, 2″-terpyridine) Ru(II)-COMPLEXES STABILIZED GOLD NANOPARTICLES AND THEIR ELECTRO CATALYTIC REDUCTION OF NITRITE

Margandan¹,

Jebastin²

2017

J. Chil. Chem. Soc.

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Inorganic-organic hybrid structures based on metal-complexes particularly, octahedral bis-2,2':6',2''-terpyridine metal complexes provide an advantages of increased symmetry and in the case of ruthenium(III)/ruthenium(II) complexation an entrance to a directed complexation Method. The Ru (II) terpyridine methane thiolate protected gold nanoparticle was synthesized through covalent bonding of Ru terpyridine methane thiolates over gold nanoparticles surfaces. The ligand terpyridine methanethiolate was synthesized successfully in good percentage of yield. The structures were confirmed and characterized by different physical, analytical, spectral data like FTIR, UV, SEM and Cyclic voltammetry. All the data are shown the expected results.

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The Reaction of Enaminones with Carboxamidines: A Convenient Route for the Synthesis of Polyaza Heterocycles

Cited by 75 publications

References 0 publications

Recent development in preparation reactivity and biological activity of enaminoketones and enaminothiones and their utilization to prepare heterocyclic compounds

Recent development in preparation reactivity and biological activity of enaminoketones and enaminothiones and their utilization to prepare heterocyclic compounds

Pyrazole‐Based Ligands for the [Copper–TEMPO]‐Mediated Oxidation of Benzyl Alcohol to Benzaldehyde and Structures of the Cu Coordination Compounds

SYNTHESIS AND CHARACTERIZATION OF BISMERCAPTO (2, 2′:6′, 2″-terpyridine) Ru(II)-COMPLEXES STABILIZED GOLD NANOPARTICLES AND THEIR ELECTRO CATALYTIC REDUCTION OF NITRITE

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The Reaction of Enaminones with Carboxamidines: A Convenient Route for the Synthesis of Polyaza Heterocycles

Cited by 75 publications

References 0 publications

Recent development in preparation reactivity and biological activity of enaminoketones and enaminothiones and their utilization to prepare heterocyclic compounds

Recent development in preparation reactivity and biological activity of enaminoketones and enaminothiones and their utilization to prepare heterocyclic compounds

Pyrazole‐Based Ligands for the [Copper–TEMPO]‐Mediated Oxidation of Benzyl Alcohol to Benzaldehyde and Structures of the Cu Coordination Compounds

SYNTHESIS AND CHARACTERIZATION OF BISMERCAPTO (2, 2&#8242;:6&#8242;, 2&#8243;-terpyridine) Ru(II)-COMPLEXES STABILIZED GOLD NANOPARTICLES AND THEIR ELECTRO CATALYTIC REDUCTION OF NITRITE

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SYNTHESIS AND CHARACTERIZATION OF BISMERCAPTO (2, 2′:6′, 2″-terpyridine) Ru(II)-COMPLEXES STABILIZED GOLD NANOPARTICLES AND THEIR ELECTRO CATALYTIC REDUCTION OF NITRITE