Hydrogen-Bonding in Cyclic 2-(3-Oxo-3-phenylpropyl)-Substituted 1,3-Diketones: 17O-NMR Spectra and X-Ray Structure Determination

Zhuo, Jin‐Cong; Schenk, Kurt

doi:10.1002/1522-2675(200205)85:5<1276::aid-hlca1276>3.0.co;2-i

Cited by 7 publications

(1 citation statement)

References 10 publications

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“…Thus, we envisioned forming 1,5-dicarbonyl compounds by the reaction of Mannich salts with cyclohexanone 18 or from cyclohexanone-derived enaminones. [19][20][21] In this work, cyclohexane-1,4-dione monoethylene acetal (8) was utilized. Based on the retrosynthetic plan depicted in Scheme 2, we anticipated efficient formation of 2-aryl-7,8-dihydroquinolin-6(5H)-ones 12 from ketals 13 which can be produced from 1,5-diketones 14, which are projected to arise from the Michael addition between Mannich salts 15 and cyclohexane-1,4-dione monoethylene acetal (8).…”

Section: Paper Synthesismentioning

confidence: 99%

Synthesis and Cytotoxic Evaluation of 2-Aryl-7,8-dihydroquinolin-6(5H)-ones

Blé González,

Martínez,

Bautista

et al. 2023

Synthesis

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Herein we present a facile four-step synthetic method for the synthesis of novel 2-aryl-substituted 7,8-dihydroquinolin-6(5H)-ones as cytotoxic agents. The key step was the use of Mannich salts derived from acetophenones as a Michael acceptor in the reaction with cyclohexane-1,4-dione monoethylene acetal to give 1,5-dicarbonyl compounds that were treated with ammonium acetate to give the 7,8-dihydroquinolin-6(5H)-ones. The cytotoxic activity of the synthesized compounds was evaluated against seven cell lines. The observed data showed good selectivity for chronic myeloid leukemia line K-562. The synthetic route was simple and applicable to various functional group containing substrates. These types of compounds may be utilized as lead compounds in cancer research and drug discovery.

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Section: Paper Synthesismentioning

confidence: 99%

Synthesis and Cytotoxic Evaluation of 2-Aryl-7,8-dihydroquinolin-6(5H)-ones

Blé González,

Martínez,

Bautista

et al. 2023

Synthesis

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Facile Endoperoxypropellane Synthesis by Manganese(III) Acetate‐Mediated Aerobic Oxidation

Asahi

Nishino

2008

Eur J Org Chem

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Manganese(III)-catalyzed aerobic oxidation of combinations of 3-(2-oxoethyl)piperidine-2,4-diones and 1,1-diarylethenes at room temperature produced structurally interesting trioxaaza[4.4.3]propellanes in good yields. Similar reactions using 2-(2-oxoethyl)cyclohexane-1,3-diones also produced the corresponding endoperoxy [4.4.3]propellanes. On the other hand, 3-oxopropyl-substituted cycloalkane-1,3-diones did

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Enantioselective Ring Opening of meso‐Epoxides with Silicon Tetrachloride Catalyzed by Pyridine N‐Oxides Fused with the Bicyclo[3.3.1]nonane Framework

Neniškis

Stončius

2015

Eur J Org Chem

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The synthesis of new chiral Lewis basic organocatalysts that contain pyridine N-oxide moieties fused with the bicyclo-[3.3.1]nonane framework is reported. The obtained pyridine N-oxides were employed as catalysts in the enantioselective ring opening of meso-epoxides with silicon tetrachloride. Derivative 1b endowed with two 2,4-diaryl-substituted pyridine N-oxide moieties proved to be a particularly effective cata-6359 lyst for desymmetrization of norbornene oxide 16i to furnish Wagner-Meerwein rearrangement product 20i in unprecedented 96 % ee. Difunctional congener 3, which is striped of the 4-aryl substituents, exhibited moderate to high levels of asymmetric induction (47-88 % ee) with alicyclic epoxide substrates.N,NЈ-dioxide L3, [8] helical chiral N-oxide L4, [9] bipyridine N-monooxide L5 (PINDOX), [10] as well as dipyridylmethane, [11] bis(tetrahydroisoquinoline) [12] and bipyridine [13] N,NЈ-dioxides promote enantioselective chlorohydrin formation. Figure 1. Selected Lewis basic pyridine-type N-oxide and phosphine oxide organocatalysts.Chiral phosphine oxides, such as axially chiral L6 (BI-NAPO), [14] its heteroaromatic congeners, [15] or allene-derived bisphosphine oxide L7, [16] have been also shown to A. Neniškis, S. Stončius FULL PAPERcatalyze enantioselective ring-opening of meso-epoxides with SiCl 4 . Nevertheless, the Lewis basic catalysts developed so far proved to be rather fastidious with respect to the epoxide substrate. As a rule, the ability to impart high levels of enantioselection is limited to the derivatives of cisstilbene oxide (87-97 % ee with catalysts L1-L4, L6, and L7), whereas in the case of the less sterically demanding aliphatic substrates and, in particular, with cyclic epoxides, the enantioselectivity drops to moderate levels. Pinene-derived N-monooxide PINDOX [10] (L5; Figure 1), which is most effective with saturated cyclic substrates that contain more than seven carbon atoms and norbornene oxide (87-90 % ee) but inefficient with cis-stilbene oxide (16 % ee), is a notable exception.Desymmetrization of meso-epoxides is an attractive strategy for asymmetric synthesis as two contiguous stereogenic centers can be unveiled through a single transformation. [17] Therefore further development, which enhances the catalyst efficiency and broadens the scope of such reactions is desirable. Herein we present the synthesis of new Lewis bases that feature a pyridine N-oxide fragment attached to a chiral bicyclo[3.3.1]nonane backbone, and their application in enantioselective ring opening of meso-epoxides with silicon tetrachloride. www.eurjoc.org 6361 Scheme 2. Reagents and conditions: (a) TiCl 4 , Cl(CH 2 ) 2 COCl, 1,2-DCE; (b) TEA, CH 2 Cl 2 (18-43 %); (c) (i) DMF, POCl 3 , 0°C (98 %), (ii) H 2 C=CHMgBr, THF, 0°C (80 %); (d) IBX, THF/ DMSO, room temp. (67 %); (e) Me 2 NH 2 Cl, iPrOH, Δ (91 %); (f) 4, TEA, 180°C, then NH 2 OH·HCl, EtOH, Δ (30 %); (g) m-CPBA, K 2 CO 3 , CH 2 Cl 2 , room temp. (38 %).

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Hydrogen-Bonding in Cyclic 2-(3-Oxo-3-phenylpropyl)-Substituted 1,3-Diketones: 17O-NMR Spectra and X-Ray Structure Determination

Cited by 7 publications

References 10 publications

Synthesis and Cytotoxic Evaluation of 2-Aryl-7,8-dihydroquinolin-6(5H)-ones

Synthesis and Cytotoxic Evaluation of 2-Aryl-7,8-dihydroquinolin-6(5H)-ones

Facile Endoperoxypropellane Synthesis by Manganese(III) Acetate‐Mediated Aerobic Oxidation

Enantioselective Ring Opening of meso‐Epoxides with Silicon Tetrachloride Catalyzed by Pyridine N‐Oxides Fused with the Bicyclo[3.3.1]nonane Framework

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