- Generation and trapping of electron-deficient 1,2-cyclohexadienes. Unexpected hetero-Diels-Alder reactivity
-
Keto-substituted 1,2-cyclohexadienes were generated by base-mediated (KOt-Bu) elimination, and found to dimerize via an unprecedented formal hetero-Diels-Alder process, followed by hydration. These highly reactive cyclic allene intermediates were also tra
- Wang, Baolei,Constantin, Marius-Georgian,Singh, Simarpreet,Zhou, Yuqiao,Davis, Rebecca L.,West
-
supporting information
p. 399 - 405
(2021/01/29)
-
- Synthesis of small molecules targeting paclitaxel-induced MyD88 expression in triple-negative breast cancer cell lines
-
Acquired paclitaxel (PTX) chemoresistance in triple-negative breast cancer (TNBC) can be inferred from the overexpression of toll-like receptor 4 (TLR4) and myeloid differentiation primary response 88 (MyD88) proteins and the activation of the TLR4/MyD88 cascading signalling pathway. Finding a new inhibitor that can attenuate the activation of this pathway is a novel strategy for reducing PTX chemoresistance. In this study, a series of small molecule compounds were synthesised and tested in combination with PTX against TNBC cells. The trimethoxy-substituted compound significantly decreased MyD88 overexpression and improved PTX activity in MDA-MB-231TLR4+ cells but not in HCCTLR4? cells. On the contrary, the trifluoromethyl-substituted compound with PTX synergistically improved the growth inhibition in both TNBC subtypes. The fluorescence titrations indicated that both compounds could bind with MD2 with good and comparable binding affinities. This was further supported by docking analysis, in which both compounds fit perfectly well and form some critical binding interactions with MD2, an essential lipid-binding accessory to TLR4 involved in activating the TLR-4/MyD88-dependent pathway.
- Poh Yen, Khor,Stanslas, Johnson,Zhang, Tianshu,Li, Hongyuan,Wang, Xiaohui,Kok Meng, Chan,Kok Wai, Lam
-
-
- The involvement of l-arginine-nitric oxide-cgmp-atp-sensitive k+ channel pathway in antinociception of bbhc, a novel diarylpentanoid analogue, in mice model
-
The present study focuses on the possible involvement of L-arginine-nitric oxide-cGMP-ATP-sensitive K+ channel pathway in the antinociceptive activity of a novel diarylpentanoid analogue, 2-benzoyl-6-(3-bromo-4-hydroxybenzylidene)cyclohexen-1-ol (BBHC) via a chemical nociceptive model in mice. The antinociceptive action of BBHC (1 mg/kg, i.p.) was attenuated by the intraperi-toneal pre-treatment of L-arginine (a nitric oxide synthase precursor) and glibenclamide (an ATP-sensitive K+ channel blocker) in acetic acid-induced abdominal constriction tests. Interestingly, BBHC’s antinociception was significantly enhanced by the i.p. pre-treatment of 1H-[1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one (ODQ), a selective inhibitor of soluble guanylyl cyclase (p + channel pathway, without any potential sedative or muscle relaxant concerns.
- Abas, Faridah,Ahmad Azmi, Ahmad Farhan,Farouk, Ahmad Akira Omar,Israf, Daud Ahmad,Leong, Sze Wei,Ong, Hui Ming,Perimal, Enoch Kumar,Sulaiman, Mohd Roslan
-
-
- Three-Component Coupling of Acyl Fluorides, Silyl Enol Ethers, and Alkynes by P(III)/P(V) Catalysis
-
We report herein on the phosphine-catalyzed hydrovinylation reaction by three-component coupling of acyl fluorides, silyl enol ethers, and alkynoates. The key to the success of the reaction is the formal transmetalation between pentacoordinate P(V) species (i.e., fluorophosphorane) and a silyl enol ether, which allows for C-C bond formation between the polarity-mismatched sites. The bond formation that cannot be attained even by transition metal catalysis is accomplished by a P(III)/P(V) manifold.
- Fujimoto, Hayato,Kusano, Momoka,Kodama, Takuya,Tobisu, Mamoru
-
supporting information
p. 18394 - 18399
(2021/11/22)
-
- Design and synthesis of a novel mPGES-1 lead inhibitor guided by 3D-QSAR CoMFA
-
The search of novel mPGES-1 inhibitors has recently intensified probably due to the superior safety in comparison to existing anti-inflammatory drugs. Although two mPGES-1 inhibitors have entered clinical trials, none has yet reached the market. In this study, we performed modifications guided by 3D-QSAR CoMFA on 2, which is an unsymmetrical curcumin derivative with low binding affinity towards mPGES-1. To counter the PAINS properties predicted for 2, the diketone linker was replaced with a pyrazole ring. On the other hand, both prenyl and carboxylate ester groups were introduced to improve the activity. When tested in vitro, 11 suppressed PGE2 biosynthesis in activated macrophages and showed promising human mPGES-1 inhibition in microsomes of interleukin-1β-stimulated A549 cells. Altogether, 11 has been identified as a potential mPGES-1 inhibitor and could be a promising lead for a novel class of mPGES-1 inhibitors.
- Fasihi Mohd Aluwi, Mohd Fadhlizil,Rullah, Kamal,Koeberle, Andreas,Werz, Oliver,Abdul Razak, Nur Sakinah,Wei, Leong Sze,Salim, Fatimah,Ismail, Nor Hadiani,Jantan, Ibrahim,Wai, Lam Kok
-
p. 844 - 850
(2019/07/12)
-
- Synthesis of 1,3-Diketones and β-Keto Thioesters via Soft Enolization
-
Ketones and thioesters undergo soft enolization and acylation using crude acid chlorides on treatment with MgBr2·OEt2 and i-Pr2NEt to give 1,3-diketones and β-keto thioesters, respectively. The use of crude acid chlorides adds efficiency and cost reduction by avoiding the need to purify and/or purchase them. The process is conducted in a direct fashion that does not require prior enolate formation, further enhancing its efficiency and making it very easy to carry out. The method is suitable for large scale applications. ?
- Aderibigbe, Sabrina O.,Coltart, Don M.
-
p. 9770 - 9777
(2019/08/27)
-
- In vitro and in silico evaluations of diarylpentanoid series as α-glucosidase inhibitor
-
A series of thirty-four diarylpentanoids derivatives were synthesized and evaluated for their α-glucosidase inhibitory activity. Eleven compounds (19, 20, 21, 24, 27, 28, 29, 31, 32, 33 and 34) were found to significantly inhibit α-glucosidase in which compounds 28, 31 and 32 demonstrated the highest activity with IC50 values ranging from 14.1 to 15.1 μM. Structure-activity comparison shows that multiple hydroxy groups are essential for α-glucosidase inhibitory activity. Meanwhile, 3,4-dihydroxyphenyl and furanyl moieties were found to be crucial in improving α-glucosidase inhibition. Molecular docking analyses further confirmed the critical role of both 3,4-dihydroxyphenyl and furanyl moieties as they bound to α-glucosidase active site in different mode. Overall result suggests that diarylpentanoids with both five membered heterocyclic ring and polyhydroxyphenyl moiety could be a new lead design in the search of novel α-glucosidase inhibitor.
- Leong, Sze Wei,Abas, Faridah,Lam, Kok Wai,Yusoff, Khatijah
-
p. 302 - 309
(2018/01/03)
-
- Suppression of PGE2 production via disruption of MAPK phosphorylation by unsymmetrical dicarbonyl curcumin derivatives
-
Curcumin is an important molecule found in turmeric plants and has been reported to exhibit some profound anti-inflammatory activities by interacting with several important molecular targets found in the mitogen-activated protein kinase and NF-κβ pathways. As part of our continuing effort to search for new anti-inflammatory agents with better in vitro and in vivo efficacies, we have synthesized a series of new unsymmetrical dicarbonyl curcumin derivatives and tested their effects on prostaglandin E2 secretion level in interferon-γ/lipopolysaccharide-activated macrophage cells. Among those, five compounds exhibited remarkable suppression on prostaglandin E2 production with IC50 values ranging from 0.87 to 18.41 μM. The most potent compound 17f was found to down-regulate the expression of cyclooxygenase-2 mRNA suggesting that this series of compounds could possibly target the mitogen-activated protein kinase signal transduction pathway. Whilst the compound did not affect the expression of the conventional mitogen-activated protein kinases, the results suggest that it could disrupt the phosphorylation and activation of the proteins particularly the c-Jun N-terminal kinases. Finally, the binding interactions were examined using the molecular docking and dynamics simulation approaches.
- Mohd Aluwi, Mohd Fadhlizil Fasihi,Rullah, Kamal,Haque, Md. Areeful,Yamin, Bohari M.,Ahmad, Waqas,Amjad, Muhammad Wahab,Leong, Sze Wei,Fahmizar, Nurul Amira,Jalil, Juriyati,Abas, Faridah,Ismail, Nor Hadiani,Jantan, Ibrahim,Lam, Kok Wai
-
p. 3323 - 3335
(2017/10/06)
-
- Trimethylchlorosilane-Mediated Mild α-Chlorination of 1,3-Dicarbonyl Compounds Promoted by Phenyliodonium Diacetate
-
Trimethylchlorosilane was used as chlorine source for the α-chlorination of 1,3-dicarbonyl compounds with phenyliodonium diacetate as oxidant at room temperature. The reaction allows the selective synthesis of α-monochlorinated products from different kinds of 1,3-dicarbonyl compounds in good yield. The potential possibility of this conversion for bromination has also been investigated.
- Chong, Siying,Su, Yingpeng,Wu, Lili,Zhang, Weigang,Ma, Junyan,Chen, Xiaowei,Huang, Danfeng,Wang, Ke-Hu,Hu, Yulai
-
supporting information
p. 1359 - 1370
(2016/05/02)
-
- 2-Benzoyl-6-benzylidenecyclohexanone analogs as potent dual inhibitors of acetylcholinesterase and butyrylcholinesterase
-
In the present study, a series of 2-benzoyl-6-benzylidenecyclohexanone analogs have been synthesized and evaluated for their anti-cholinesterase activity. Among the forty-one analogs, four compounds (38, 39, 40 and 41) have been identified as lead compounds due to their highest inhibition on both AChE and BChE activities. Compounds 39 and 40 in particular exhibited highest inhibition on both AChE and BChE with IC50values of 1.6?μM and 0.6?μM, respectively. Further structure–activity relationship study suggested that presence of a long-chain heterocyclic in one of the rings played a critical role in the dual enzymes’ inhibition. The Lineweaver–Burk plots and docking results suggest that both compounds could simultaneously bind to the PAS and CAS regions of the enzyme. ADMET analysis further confirmed the therapeutic potential of both compounds based upon their high BBB-penetrating. Thus, 2-benzoyl-6-benzylidenecyclohexanone containing long-chain heterocyclic amine analogs represent a new class of cholinesterase inhibitor, which deserve further investigation for their development into therapeutic agents for cognitive diseases such as Alzheimer.
- Leong, Sze Wei,Abas, Faridah,Lam, Kok Wai,Shaari, Khozirah,Lajis, Nordin H.
-
p. 3742 - 3751
(2016/07/20)
-
- Nitric oxide inhibitory activity and antioxidant evaluations of 2-benzoyl-6-benzylidenecyclohexanone analogs, a novel series of curcuminoid and diarylpentanoid derivatives
-
Abstract A series of twenty-four 2-benzoyl-6-benzylidenecyclohexanone analogs were synthesized and evaluated for their nitric oxide inhibition and antioxidant activity. Six compounds (3, 8, 10, 17, 18 and 19) were found to exhibit significant NO inhibitory activity in LPS/IFN-induced RAW 264.7 macrophages, of which compound 10 demonstrated the highest activity with the IC50 value of 4.2 ± 0.2 μM. Furthermore, two compounds (10 and 17) displayed antioxidant activity upon both the DPPH scavenging and FRAP analyses. However, none of the 2-benzoyl-6-benzylidenecyclohexanone analogs significantly scavenged NO radical. Structure-activity comparison suggested that 3,4-dihydroxylphenyl ring is crucial for bioactivities of the 2-benzoyl-6-benzylidenecyclohexanone analogs. The results from this study and the reports from previous studies indicated that compound 10 could be a candidate for further investigation on its potential as a new anti-inflammatory agent.
- Leong, Sze Wei,Mohd Faudzi, Siti Munirah,Abas, Faridah,Mohd Aluwi, Mohd Fadhlizil Fasihi,Rullah, Kamal,Lam, Kok Wai,Abdul Bahari, Mohd Nazri,Ahmad, Syahida,Tham, Chau Ling,Shaari, Khozirah,Lajis, Nordin H.
-
p. 3330 - 3337
(2015/07/08)
-
- Discovery of 2-(1H-indazol-1-yl)-thiazole derivatives as selective EP 1 receptor antagonists for treatment of overactive bladder by core structure replacement
-
We have designed a series of potent EP1 receptor antagonists. These antagonists are a series of 2-(1H-indazol-1-yl)-thiazoles in which the core structure was replaced with pyrazole-phenyl groups. In preliminary conscious rat cystometry experiments, two representative candidates, 2 and 22, increased bladder capacity. In particular, the increase using 22 was approximately 2-fold that of the baseline. More detailed profiling of this compound and further optimization of this series promises to provide a novel class of drug for treating overactive bladder (OAB).
- Atobe, Masakazu,Naganuma, Kenji,Kawanishi, Masashi,Morimoto, Akifumi,Kasahara, Ken-Ichi,Ohashi, Shigeki,Suzuki, Hiroko,Hayashi, Takahiko,Miyoshi, Shiro
-
p. 1327 - 1333
(2014/03/21)
-
- Regiochemistry of the condensation of 2-aroyl-cyclohexanones and 2-cyanoacetamide: 13C-labeling studies and semiempirical MO calculations
-
Hydroxy-aryl-5,6,7,8-tetrahydroisoquinoline-4-carbonitriles represent interesting chemical scaffolds, but synthetic access to these compounds is limited. The reaction of 2-aroyl-cyclohexanones with 2-cyanoacetamide and base in ethanol has been reported to
- Van Linden, Oscar P. J.,Wijtmans, Maikel,Roumen, Luc,Rotteveel, Lonneke,Leurs, Rob,De Esch, Iwan. J. P.
-
p. 7355 - 7363
(2012/11/07)
-
- Fragment based lead discovery of small molecule inhibitors for the EPHA4 receptor tyrosine kinase
-
The in silico identification, optimization and crystallographic characterization of a 6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c]isoquinolin-1-amine scaffold as an inhibitor for the EPHA4 receptor tyrosine kinase is described. A database containing commercially
- Van Linden, Oscar P.J.,Farenc, Carine,Zoutman, Willem H.,Hameetman, Liesbeth,Wijtmans, Maikel,Leurs, Rob,Tensen, Cornelis P.,Siegal, Gregg,De Esch, Iwan J.P.
-
supporting information; experimental part
p. 493 - 500
(2012/03/11)
-
- Iridium-catalyzed reaction of enones with alcohols affording 1,3-diketones
-
An iridium-catalyzed coupling reaction of alcohols with enones has been successfully developed providing access to 1,3-diketones with high selectivity in good yields. This reaction provides an atom-economical route to 1,3-diketones from readily available
- Obora, Yasushi,Nakamura, Kazuhiro,Hatanaka, Shintaro
-
supporting information; experimental part
p. 6720 - 6722
(2012/07/17)
-
- NEW BICYCLIC DIOXANES, THEIR PREPARATION AND THEIR USE AS FRAGRANT COMPOUNDS
-
The invention is directed to the use of compounds of formula (I), as fragrant agents. In this formula: - R3 and R4 are independently a hydrogen atom, a C1-C6 alkyl group or a C2-C6 alkenyl group, R5 is a C1-C6 alkyl group, a C2-C6 alkenyl group or a (CH2)0-2-aryl group, R6 is a C1 -C6 alkyl group, a C2-C6 alkenyl group, a (CH2)0-2-aryl group or a C5- C6 cycloalkyl or cycloalkenyl group, and R7 is a hydrogen atom, a C1-C6 alkyl group or a C2-C6 alkenyl group; or R3, R4 and R5 are as above defined, and R6 and R7 together with the carbon atom to which they are attached form a C5-C6 cycloalkyl or cycloalkenyl group.
- -
-
Page/Page column 10
(2011/02/24)
-
- New bicyclic dioxanes, their preparation and their use as organoleptic compounds
-
The present invention relates to novel 1,3-dioxane derivatives of formula (I) wherein each of R1 and R2 is a hydrogen atom, R3 and R4 are independently a hydrogen atom, a linear or branched C1-C6 alkyl group, or a linear or branched C2-C6 alkenyl group, and R5 is a linear or branched C1-C6 alkyl group, a linear or branched C2-C6 alkenyl group or a (CH2)0-2 - aryl group, and R6 and R7 are independently a hydrogen atom, a linear or branched C1-C6 alkyl group, a linear or branched C2-C6 alkenyl group or a (CH2)0-2 - aryl group, or R6 and R7 together with the carbon atom to which they are attached form a C5-C6 cycloalkyl group or a C5-C6 cycloalkenyl group, substituted or not; their preparation and their use as organoleptic compounds.
- -
-
Page/Page column 9
(2011/04/14)
-
- Direct synthesis of 1,3-diketones by Rh-catalyzed reductive α-acylation of enones
-
(Chemical Equation Presented) 1,3-Diketones were synthesized from α,β-unsaturated ketones by treatment with acid chlorides and Et 2Zn in the presence of RhCl(PPh3)3. This is a very simple and extremely chemoselective reaction to give the adduct at the α-position of α,β-unsaturated ketones.
- Sato, Kazuyuki,Yamazoe, Satoshi,Yamamoto, Rie,Ohata, Shizuka,Tarui, Atsushi,Omote, Masaaki,Kumadaki, Itsumaro,Ando, Akira
-
supporting information; experimental part
p. 2405 - 2408
(2009/05/11)
-
- Triethylgallium as a nonnucleophilic base to generate enolates from ketones
-
(Chemical Equation Presented) Triethylgallium deprotonated cyclic and acyclic ketones at 125-175°C without forming carbonyl addition products, and the resulting gallium enolates underwent facile C-benzoylation and an aldol reaction. Unsymmetrical ketones were preferentially enolized at the methylene moiety, which was under kinetic control.
- Nishimura, Yoshio,Miyake, Yutaka,Amemiya, Ryo,Yamaguchi, Masahiko
-
p. 5077 - 5080
(2007/10/03)
-
- The preparation and reaction of enolates within micro reactors
-
Over the past 5 years, interest in the miniaturisation of chemical synthesis has grown rapidly, however in order to facilitate transfer of the technology from its current position as a research tool to industrial applications, a core understanding of the challenges associated with transferring reactions from the macro to the micro domain is required. This paper therefore aims to broach this problem by investigating the application of micro reactors to a range of commonly employed synthetic reactions including acylation, aldol, alkylation, 1,4-conjugate addition (Michael addition) and the Knoevenagel condensation. Comparison of the results obtained with traditional batch techniques enable us to highlight some of the advantages associated with micro reaction technology.
- Wiles, Charlotte,Watts, Paul,Haswell, Stephen J.,Pombo-Villar, Esteban
-
p. 10757 - 10773
(2007/10/03)
-
- Synthesis of the core bicyclic system of hyperforin and nemorosone
-
A direct synthesis of analogs of hyperforin and nemorosone containing the key bicyclic unit was accomplished from 2-carboxyethylcyclohexanone and benzoylcyclohexanone. Key steps included a manganic acetate-mediated cyclization and the formation of the bet
- Kraus, George A.,Nguyen, Tuan H.,Jeon, Insik
-
p. 659 - 661
(2007/10/03)
-
- The regioselective preparation of 1,3-diketones
-
The regioselectivity of the acylation of Li enolates and silyl enol ethers is reported using acyl halides and acyl cyanides. We illustrate a simple method for the preparation of 1,3-diketones via the silyl enol ether in excellent yields, free from competing O-acylation and diacylation products.
- Wiles, Charlotte,Watts, Paul,Haswell, Stephen J.,Pombo-Villar, Esteban
-
p. 2945 - 2948
(2007/10/03)
-
- The regioselective preparation of 1,3-diketones within a micro reactor
-
We demonstrate a simple method for the regioselective preparation of 1,3-diketones within a micro reactor from silyl enol ethers where the products are free from both competing O-acylation and diacylation products.
- Wiles, Charlotte,Watts, Paul,Haswell, Stephen J.,Pombo-Villar, Esteban
-
p. 1034 - 1035
(2007/10/03)
-
- Process for base-promoted condensation reactions and base reagent therefor
-
A method for the preparation of 1,3-diketones is disclosed wherein the method comprises the steps of:(A) mixing an alkali metal base with a hindered alcohol in an aromatic hydrocarbon solvent;(B) boiling the mixture and azeotropically distilling water formed by the reaction between the base and the alcohol, whereby a solution of a hindered alkali metal alkoxide is formed in situ in the solvent;(C) mixing an ester with the solution of the hindered alkali metal alkoxide in the aromatic hydrocarbon solvent; and then(D) adding a ketone to the mixture.
- -
-
-
- 1,3-Diarylcycloalkanopyrazoles and diphenyl hydrazides as selective inhibitors of cyclooxygenase-2
-
Novel 1,3-diarylcycloalkanopyrazoles 1, and diphenyl hydrazides 2 were identified as selective inhibitors of cyclooxygenase-2. The 1,3-diaryl substitution pattern of the pyrazole ring in 1 differentiates these compounds from most of the known selective COX-2 inhibitors that contain two aryl rings at the adjacent positions on a heterocyclic or a phenyl ring. Similarly, the two phenyl rings in 2 are also separated by three atoms. SAR of both phenyl rings in 1 and 2, and the aliphatic ring in 1 will be discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.
- Sui, Zhihua,Guan, Jihua,Ferro, Michael P.,McCoy, Kathy,Wachter, Michael P.,Murray, William V.,Singer, Monica,Steber, Michele,Ritchie, Dave M.,Argentieri, Dennis C.
-
p. 601 - 604
(2007/10/03)
-
- InCl3: A new Lewis acid catalyst for reactions with α-diazocarbonyl compounds
-
The use of InCl3 as a Lewis acid catalyst in diazocarbonyl S-H insertion reactions, nitrile cyclizations and addition reactions to aldehydes and ketones is described.
- Sengupta, Saumitra,Mondal, Somnath
-
p. 8685 - 8688
(2007/10/03)
-
- Clay catalysis: Storks alkylation and acylation of cyclohexanone without isolation of enamine
-
Cyclohexanone and morpholine in the presence of KSF under azeotropic distillation gave 1-morpholinocyclohexane which is alkylated or acylated in situ without isolation of the enamine. The overall yield of these Stork's reactions are better or equivalent to those obtained by isolation of the enamine.
- Hammadi,Villemin
-
p. 2901 - 2904
(2007/10/03)
-
- Synthesis of Isomeric Series of Aryltetrahydrobenzisoxazoles and Arylcyclopentisoxazoles
-
Four series of potential PAF-antagonists in which the isoxazole nucleus is condensed with a polyhydrogenated five- or six-carbon ring were prepared.The synthesis of the compounds 3-aryl-4,5,6,7-tetrahydrobenzisoxazoles 1, 3-arylcyclopentisoxazole 2,
- Fos, Empar,Borras, Liset,Gasull, Maria,Mauleon, David,Carganico Germano
-
p. 203 - 208
(2007/10/02)
-
- IMINOALKYLATION DES ENAMINES AVEC DES NITRILES VIA LE SEL DE NITRILIUM : UNE NUOVELLE METHODE DE SYNTHESE D'ENAMINOCETONES ET DE β-DICETONES
-
The reaction of nitrilium salts with enamines leads to a mixture of enamines 4 and enaminoketones 5 by an iminoalkylation reaction.Partial hydrolysis of 4 with diluted acetic acid leads to the isolation of these new enaminoketones 5 in high yields.Refluxi
- Baudoux, Dominique,Fuks, Robert
-
p. 1009 - 1018
(2007/10/02)
-
- A NEW METHOD FOR ACYLATION OF ENOLATES BY MEANS OF DIALKYL ACYLPHOSPHONATES AS ACYLATING AGENTS
-
Acylations of various enolates by means of diethyl acylphosphonates were described.For the acylation of acetophenone, lithium bis(trimethylsilyl)amide (LSA) was found to be suitable as the base.The scope and limitation of the benzoylation using diethyl benzoylphosphonates were also described.
- Sekine, Mitsuo,Kume, Akiko,Nakajima, Masashi,Hata, Tsujiaki
-
p. 1087 - 1090
(2007/10/02)
-
- Preparation of 1,3-Diketones and of Nitro-diketones by (1:1)-Acylation of Lithium Enolates with Acyl Chlorides
-
Slow addition of precooled solutions of lithium enolates in THF to solutions of equimolar amounts of acyl chlorides in the same solvent at temperatures between -80 and -100 deg furnishes 1,3-diketones in acceptable to good yields.Even 3-nitropropionyl and 4-nitrobutyryl chloride can be employed for the (1:1)-acylation of enolates to give the synthetically useful 5- and 6-nitro-1,3-diketones 13 and 25, respectively.The scope and the limitations of this method of preparing 1,3-diketones are given and are compared with alternative methods.
- Seebach, Dieter,Weller, Thomas,Protschuk, Gerd,Beck, Albert K.,Hoekstra, Marvin S.
-
p. 716 - 735
(2007/10/02)
-