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Titanium Enolate Chemistry at the Beginning of the 21st Century

The aim of the microreview is to summarize the current state of knowledge in the field of titanium enolate chemistry. The authors focus on stereoselective organic syntheses promoted by titanium enolates and analyze developments in the synthetic methodology observed in this area during the last fifteen years. This microreview covers areas of current applications of titanium(IV) enolates in modern organic synthesis. It focuses on recent developments in the field of titanium(IV)-mediated aldol, aldol-like, Mannich, and Michael reactions, radical alkylation, oxidative couplings, and Morita-Baylis-Hillman reactions with special emphasis on the last fifteen years.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H444NO – PubChem

 

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Effect of stoichiometry on the thermal stability and flame retardation of polyisocyanurate foams modified with epoxy resin

Epoxy resin modified polyisocyanurate (EP-PIR) foams were successfully prepared by the reaction of polymethylene polyphenylene isocyanate (PAPI) and diglycidyl ether of bisphenol-A (DGEBA). Thermogravimetric analysis coupled with infrared spectrometry (TGA-IR) was performed to investigate the thermostability and the gaseous pyrolysis products of EP-PIR foams. The results indicated that the excellent thermostability of EP-PIR foams was due to the abundant highly thermostable isocyanurate ring and oxazolidone ring. The flame retardation of EP-PIR foams was also investigated. UL94 results revealed that the foams with [PAPI]/[DGEBA] ratio above 2.5 could reach V-0 classification. With increasing the stoichiometry of [PAPI]/[DGEBA], the limiting oxygen index values increased linearly from 24.5 to 30.0 vol %. Scanning electron microscopy images of burned foams illustrated the flame-retardant mechanism was due to the excellent charring ability. Cone calorimeter tests showed that the peaks of heat release rate were always as low as 266.5 kW/m2. Moreover, highly thermostable isocyanurate ring played an important role in the suppression of smoke emission.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H423NO – PubChem

 

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Non-classical anionic naked n-heterocyclic carbenes: Fundamental properties and emerging applications in synthesis and catalysis

Ongoing research exploring the chemistry of N-heterocyclic carbenes (NHCs) has led to the development and discovery of new NHC subclasses that deviate beyond Arduengo?s prototypical N,N?-disubstituted imidazol-2-ylidene-based structures. These systems continue to enable and extend the fundamental role of NHC ligands in synthesis and catalysis. In this regard, the advent of protic NHCs has garnered particular interest. This derives in part from their applications to the selective preparation of unique molecular scaffolds and their unprecedented bifunctional reactivity, which can be exploited in transition metal-catalyzed processes. In comparison, the synthetic applications of closely related anionic naked NHCs remain rather underexplored. With this in mind, this review highlights the interesting fundamental properties of non-classical anionic naked NHCs, and focuses on their emerging applications in synthesis and catalysis.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H726NO – PubChem

 

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Efficient catalytic aza-Michael additions of carbamates to enones: revisited dual activation of hard nucleophiles and soft electrophiles by InCl3/TMSCl catalyst system

The aza-Michael reaction of a variety of chalcones with weaker nucleophilic carbamates catalyzed by InCl3 in the presence of TMSCl via the entry of dual activation of both hard nucleophiles (carbamates) and soft electrophiles (enones) to provide the corresponding adducts in good yields. The first example of enantioselective aza-Michael reaction of chalcones with carbamates was also investigated in the presence of the present catalyst system.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H1168NO – PubChem

 

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A Convenient and Concise Metal-Free Approach to Functionalized Bicyclic Pyrimidinones from Oxazine-2,6-diones

The synthesis of previously unreported pyrazolo-pyrimidinones and isoxazolo-pyrimidinones are achieved via metal-free coupling of oxazine-2,6-diones with pyrazolidinone and isoxazolidinone, respectively. The synthesis provides easy access to a variety of novel 2-dimensional building blocks that can be derivatized to generate a range of drug- and agro-like molecules.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H1248NO – PubChem

 

Extended knowledge of Oxazolidin-2-one

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Female-Produced Sex Pheromone of Tetrastichus planipennisi, a Parasitoid Introduced for Biological Control of the Invasive Emerald Ash Borer, Agrilus planipennis

The Asian eulophid wasp Tetrastichus planipennisi is being released in North America as a biocontrol agent for the emerald ash borer (Agrilus planipennis), a very destructive invasive buprestid beetle that is devastating ash trees (Fraxinus spp.). We identified, synthesized, and tested a female-produced sex pheromone for the wasp. The key component eliciting behavioral responses from male wasps in flight tunnel bioassays was identified as (6S,10S)-(2E,4E,8E)-4,6,8,10-tetramethyltrideca-2,4,8-triene. Female specificity was demonstrated by gas chromatographic (GC) comparison of male and female volatile emissions and whole body extracts. The identification was aided by coupled gas chromatography/mass spectrometry analysis, microchemical reactions, NMR, GC analyses with a chiral stationary phase column, and matching GC retention times and mass spectra with those of synthetic standards. The tetramethyl-triene hydrocarbon was synthesized as a mixture of two enantiomeric pairs of diastereomers, and as the pure insect-produced stereoisomer. In flight-tunnel bioassays, males responded to both the natural pheromone and the chiral synthetic material by upwind flight and landing on the source. In contrast, the mixture of four stereoisomers was not attractive, indicating that one or more of the ?unnatural? stereoisomers antagonized attraction. Field trials, using yellow pan traps baited with natural pheromone, captured significantly more male wasps than control traps over a four week trial. The identified pheromone could increase the efficiency and specificity of the current detection methods for Tetrastichus planipennisi and aid in the determination of parasitoid establishment at release sites.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H453NO – PubChem

 

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ALKENYLDIARYLMETHANES, FUSED ANALOGS AND SYNTHESES THEREOF

Non-nucleoside inhibitors of HIV-1 reverse transcriptase are described. Such inhibitors may be used as part of a combination therapy to treat HIV infection. Compounds described herein exhibit antiviral potency. In addition, compounds described herein exhibit metabolic stability. Also described herein are processes for preparing Non-nucleoside inhibitors of HIV-1 reverse transcriptase

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H163NO – PubChem

 

Discovery of Oxazolidin-2-one

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Recent Advances in the Synthesis of Hydantoins: The State of the Art of a Valuable Scaffold

The review highlights the hydantoin syntheses presented from the point of view of the preparation methods. Novel synthetic routes to various hydantoin structures, the advances brought to the classical methods in the aim of producing more sustainable and environmentally friendly procedures for the preparation of these biomolecules, and a critical comparison of the different synthetic approaches developed in the last twelve years are also described. The review is composed of 95 schemes, 8 figures and 528 references for the last 12 years and includes the description of the hydantoin-based marketed drugs and clinical candidates.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H702NO – PubChem

 

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A modular and organocatalytic approach to gamma-butyrolactone autoregulators from Streptomycetes

A general synthesis of optically active gamma-butyrolactone autoregulators is developed by a two-step sequence to assemble 2,3-trans-disubstituted butyrolactones in high yields and enantioselectivities; the scope of this reaction was elaborated by setting up a library of alkyl-substituted butyrolactones and the synthesis of the autoregulators IM-2 and VB-D. The Royal Society of Chemistry.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H510NO – PubChem

 

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Nucleophilic reactivities of imide and amide anions

(Figure presented) The kinetics of the reactions of amide and imide anions 2a-o with benzhydrylium ions 1a-i and structurally related quinone methides 1j-q have been studied by UV-vis spectroscopy in DMSO and acetonitrile solution. The second-order rate constants (log k2) correlated linearly with the electrophilicity parameters E of 1a-q according to the correlation log k 2 = s(N + E) (Angew. Chem., Int. Ed. Engl. 1994, 33, 938-957), allowing us to determine the nucleophilicity parameters N and the nucleophile-specific parameters s for these nucleophiles. The reactivities of all sulfonamide and diacylimide anions are found in a relatively small range (15 < N < 22). Comparison with structurally related carbanions revealed that amide and imide anions are less reactive than carbanions of the same pK aH. These effects can be attributed to the absence of resonance stabilization of one of the lone pairs in the amide or imide anions. As amide and imide anions are exclusively attacked at nitrogen by benzhydrylium ions, Kornblums interpretation of the ambident reactivity of amide anions has to be revised. Balanced chemical reaction does not necessarily reveal either the individual elementary reactions by which a reaction occurs or its rate law.Reference of 497-25-6. In my other articles, you can also check out more blogs about 497-25-6

Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H372NO – PubChem