Alkyl 3-nitroacrylates: Synthesis and reactions with cyclohexane-1,3-diones and Meldrum’s acid

A modified procedure was proposed for the synthesis of alkyl 3-nitroacrylates by nitroiodination of alkyl acrylates and subsequent dehydroiodination of iodonitropropanoates with triethylamine. Alkyl 3-nitroacrylates reacted with cyclohexane-1,3-dione, dimedone, and Meldrum’s acid in the presence of N,N,N-tri-methylanilinium hydroxide (Rodionov’s catalyst) in anhydrous methanol to give the corresponding Michael adducts.     

Versatile synthesis of quaternary 1,3-oxazolidine-2,4-diones and their use in the preparation of α-hydroxyamides

A new approach to the synthesis of 1,3-oxazolidine-2,4-diones, via a two-step reaction sequence, starting from the readily available α-ketols and isocyanates, is reported. The condensation of the latter led to the key precursors 4-methylene-2-oxazolidinones, which are converted into the diones by an oxidative cleavage of the exocyclic double bond. Thus, 5,5-disubstituted 1,3-oxazolidine-2,4-diones can be accessed in good yields from the appropriate functionalized α-ketols. Moreover, two alternative routes are also described either by functionalization of 4-oxazolin-2-ones or by alkylation of the 1,3-oxazolidine-2,4-dione core previously prepared. Upon hydrolysis of the 1,3-oxazolidine-2,4-diones, a series of α-hydroxyamides bearing a quaternary stereocenter were obtained.     

Tandem Approach to Functionalized Pyrrolo[3,4-α]carbazole-1,3-diones via a Pd-catalyzed Indole-to-carbazole Transformation

A one-pot and efficient tliree-component reaction of indoles, acrylates and maleimides for the synthesis of pyrrolo[3,4-α]carbazole-1,3-dione derivatives was developed. Three C-C bonds and one ring were created in a single step via an indole-to-carbazole transformation triggered by Pd(II)-catalyzed direct C3-alkenylation of indoles.     

Formation of 2-arylindane-1,3-diones and 3-alkylphthalides from methyl o-[α-phenylsulfonyl]toluate

2-Aryl-1,3-indanedione and phthalide derivatives have attracted considerable interest due to their anticoagulant, parasiticidal and a range of biological activities. The synthesis of 2-aryl-1,3-indanedione by the condensation of the title sulfone with aryl aldehydes through an interesting pathway and a previously unreported approach to 3-alkylphthalide from C-alkylated derivatives of 1 under microwave and conventional heating conditions are described.     

Synthesis of New 1Н-Pyrrolo[3,4-с]pyridine-1,3(2Н)-diones

Russian Journal of General Chemistry - A method for the synthesis of a series of new substituted 1H-pyrrolo[3,4-c]pyridine-1,3(2H)-diones was proposed based on the Diels–Alder type reaction...     

Regiospecific synthesis of α-chloro- and α-fluoro-1,2-diones

α-Chloro-1,2-diones and α-fluoro-1,2-diones were prepared from the corresponding α-chloroaldimines by a sequence of reactions involving cyanation to α-cyanoenamines, α-halogenation to form α-chloro- or α-fluoroimidoyl cyanides and addition of organolithium reagents across the nitrile moiety, followed by acidic hydrolysis. All steps are straightforward and occur without side reactions finally leading to regiospecifically chlorinated and fluorinated 1,2-diones in good yields.     

Hydrochlorination of δ2-1,3-oxazolines and 1,3-oxazolidines

The compounds 2-(ethoxycarbonylmethyl)-²-l,3-oxazoline and 1-methyl-2-(methoxycarbonylmethylene)-1,3-oxazolidine are hydrochlorinated at the C=N or C= C bond, respectively, with subsequent opening of the oxazolidine ring. Depending on the reaction conditions, this occurs regioselectively to form various products.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 684–686, May, 1992     

Enantioselective synthesis of spirocyclic cyclopentenes: asymmetric [3+2] annulation of 2-arylideneindane-1,3-diones with MBH carbonates derivatives catalyzed by multifunctional thiourea–phosphines

The [3+2] annulation reactions of 2-arylideneindane-1,3-diones with Morita–Baylis–Hillman (MBH) carbonates proceeded smoothly in the presence of multifunctional thiourea–phosphines to produce the corresponding quaternary carbon centered spirocyclic cyclopentenes in moderate yields, with high diastereoselectivities and enantioselectivities under mild conditions. The plausible reaction has been also discussed on the basis of previous literature.     

Acylation of 2′,5′,5′-trimethyl-4′,5′-dihydro-4H-spiro-[naphthalene-1,3′-pyrrol]-4-one with 5-arylfuran-2,3-diones

Russian Journal of Organic Chemistry -     

Synthesis of Some Potential Antiangiogenic 1,3-Dihydro-1,3-dioxo-2H-isoindole Derivatives

The proliferation, invasion and metastasis of malignant tumors are closely related withangiogenesis induced by tumor cells. Blocking tumor-induced angiogenesis is anefficient strategy to prevent and cure cancer1. Recent studies indicated that theangiogenic process depends on vascular endothelial cell migration and invasion, whichregulated by αvβ3 receptor2. The receptor and extracellular matrix can recognize eachother through Arg-Gly-Asp (RGD) consensus sequence found in matrix ligands…     

1,3-Diphosphetane-2,4-diyles--Cryptocarbenes?

1,3-Diphosphetane-2,4-diyles ( A ) possess a diradical molecular structure. Experimental studies reveal interconversions of different valence isomers of the diradicals. As a consequence of the facile thermal ring opening of 1,3-diphosphetane-2.4-diyles A , we obtained crypto-phosphinocarbenes ( B ), confirmed by the results of intramolecular rearrangements as well as reactions with multiple bonded systems. A new range of five- and six-membered phosphorus heterocycles are isolated, including transition-metal complexes. The mechanism for the ring-expansion are predicted by quantum chemical calculations.     

Sodium Trimethyl Silanoate. A Hydroxyl Synthon for Fluoride SNAr Type Displacements from Anthracene-9,10-diones,Benz[g]isoquinoline-5–10-diones and Nitrobenzenes

Treatment of fluoroanthracene-9,10-diones, fluorobenz[g]isoquinoline-5,10-diones and 1- or 4-fluoronitrobenzenes with sodium trimethylsilanoate in THF followed by acidification readily yields the corresponding hydroxyl analogues.     

1,3-丙二醇制备研究进展

1,3丙二醇（1,3-PDO）是一种重要的化工原料,可以作为溶剂、抗冻剂、增塑剂、乳化剂、防腐剂、洗涤剂和润滑剂等[1],在食品、医药、化妆品和有机合成中有着重要应用.此外,1,3-PDO还可以作为聚酯、聚醚和聚氨酯的单体．     

Synthesis and Structure of 3-Aryl-5-cyano-6-methylthio pyrimidine2,4-diones

Polarizedketenedithioacetalsl,(XY)C=C(SR)2(X,Y=CN,NO2,COOEt,CONH=,R=alkyl,benzyl).havebeenextensivelyusedasbuildingblocksinorganicsynthesisespeciallyinthepreparationofheterocycliccompounds''.Inanextensionofourrecentstudies'intheapplicationofketokete...     

Reactions of enamines with fluorinated acyl chlorides----Synthesis of fluorinated 1,3-diketones and 1,3-keto-aldehydes

The reactions of enamines (1a-b,4,6) with fluorinated acyl chlorides (2a-d) produced fluorinated 1,3-diketones (3a-f) and 1,3-keto-aldehydes (7a-c) in good yields as well as byproducts fluorinated acylamides (5a-c).It is proposed that the reactions involve nucleophilic attack by the C-atora and/or N-atom of the enamines on acyl carbon of the fluorinated acyl chlorides.     

Rational design and synthesis of some PPAR-γ agonists: Substituted benzylideneamino-benzylidene-thiazolidine-2,4-diones

The peroxisome proliferator activator receptor-γ (PPAR-γ) remained the most successful target for management of diabetes mellitus. The present work endeavors rational designing of some novel PPAR-γ agonists bearing benzylideneamino-benzylidene-thiazolidine-2,4-dione scaffold. The research involved virtual screening of 37 different molecules by molecular docking studies performed by Molecular Design Suite (MDS) into the ligand binding domain of PPAR-γ receptor to explore the binding affinity and conformations of the molecules. Eight compounds; TZD1, TZD-4, TZD-7, TZD-16, TZD-25, TZD-28, TZD-34, and TZD-37 demonstrated high affinity for PPAR-γ binding site. The following compounds were taken into the account and synthesized using a multi-step synthesis protocol. The purity of the synthesized compounds was ascertained by sophisticated analytical techniques such as IR, NMR, Mass and elemental analysis. The compounds were tested for glucose uptake assay by using 3T3-L1 cell lines, where all the candidates exhibited nearly similar potential for uptake of glucose into the lines as that of standard drug rosiglitazone. Three molecules; TZD-1, TZD-4, and TZD-34 showed most prominent activity over hyperglycemic control. This research opened new avenues for smart designing of molecules with high efficiency towards the management of hyperglycemia.     

1,3-Diphenylpropan-1,3-diamines IX. reaction of α-chlorooxime ethers with α-lithiobenzylamines

Summary The carbanions of the benzylamine derivatives1–4 have been reacted with -chlorooxime ether5 in order to get precursors of 1,3-diphenylpropane-1,3-diamines. Isonitrile1 afforded the expected result, whereas lithiated benzamide2 underwent oxidative dimerization and transmetallated chlorooxime derivative5. Isoxazolidine3 gave the condensation product21 as a mixture of diastereomers; treatment of imine4 led to the desired amine-oxime15 in low yield.Dedicated with warm regards to Prof. Dr.J. Knabe, Saarbrücken, Germany, on the occasion of his 75^th birthday     

One-pot Synthesis of 3-Aryl-1,5-bis（2-hydroxyaryl）pentane-1,5-diones

A simple method for the synthesis of 3-aryl-1,5-bis(2-hydroxyaryl)pentane-1,5-diones is developed by one-potreaction involving 2-hydroxyacetophenone and arylaldehyde in aqueous potassium hydroxide.