26-Sep-21 News Can You Really Do Chemisty Experiments About C15H11NO3

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Switchable Synthesis of Pyrroles and Pyrazines via Rh(II)-Catalyzed Reaction of 1,2,3-Triazoles with Isoxazoles: Experimental and DFT Evidence for the 1,4-Diazahexatriene Intermediate

4-Aminopyrrole-3-carboxylates and pyrazine-2-carboxylates were synthesized from 5-alkoxyisoxazoles and 1-sulfonyl-1,2,3-triazoles by tuning the Rh(II) catalyst and the reaction conditions. The reaction in chloroform at 100 degrees C under Rh-2(OAc)(4) catalysis provides 4-aminopyrrole-3-carboxylates in good yields. The use of Rh-2(Piv)(4) in refluxing toluene results in the formation of 1,2-dihydropyrazine-2-carboxylates as the main products, which can be converted by a one-pot procedure to pyrazine-2-carboxylates by heating with catalytic amounts of TsOH. According to the NMR and DFT investigations of the reaction mechanism, pyrroles and dihydropyrazines are formed, respectively, via 1,5- and 1,6-cyclization of common (5Z)-1,4-diazahexa-1,3,5-triene intermediates. The influence of the nature of the catalyst on the product distribution is rationalized in terms of the Rh-catalyzed isomerization of a pyrrolin-2-ylium-3-aminide zwitterion, the primary product of 1,4-diazahexatriene 1,5-cyclization.

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,1-Pyrroline | C4H7N – PubChem

13-Sep-2021 News The Shocking Revelation of C15H11NO3

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Enantioselective dearomative [3+2] annulation of 5-amino-isoxazoles with quinone monoimines

The first enantioselective dearomative [3+2] annulation of 5-amino-isoxazoles with quinone monoimines was realized using a chiral phosphoric acid as catalyst. Various novel (bridged) isoxazoline fused dihydrobenzofurans bearing two continuous quaternary stereocenters were achieved in moderate to good yields (up to 94%) with moderate to good enantioselectivities (up to 98% ee). The absolute configurations of two products were assigned by X-ray crystal structural analyses and a plausible reaction mechanism was proposed.

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Pyrroline – Wikipedia,
,1-Pyrroline | C4H7N – PubChem

13 Sep 2021 News The Best Chemistry compound: C15H11NO3

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Regiocontrolled synthesis of pyrrole-2-carboxaldehydes and 3-pyrrolin-2-ones from pyrrole Weinreb amides

A regiocontrolled synthesis of 3,4-disubstituted pyrrole-2carboxaldehydes was completed in two steps from acyclic starting materials. A Barton-Zard pyrrole synthesis between N-methoxy-N-methyl-2-isocyanoacetamide and R-nitroalkenes or,-nitroacetates provided N-methoxy-N-methyl pyrrole-2-carboxamides ( pyrrole Weinreb amides), which were converted into the corresponding pyrrole-2-carboxaldehydes by treatment with lithium aluminum hydride. A regioselective oxidation of the pyrrole-2-carboxaldehydes gave the corresponding 3,4-disubstituted 3-pyrrolin-2-ones.

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Pyrroline – Wikipedia,
,1-Pyrroline | C4H7N – PubChem

2-Sep-2021 News Chemical Properties and Facts of C15H11NO3

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Characterization of the amino acid adducts of the enedial derivative of teucrin A

The toxicity of germander, a herb used to treat obesity, is attributed to cytochrome P450 activation of the furan ring of its major diterpenoid component (teucrin A) into a reactive metabolite capable of adducting proteins. 1,4-Enedials have been proposed to be the reactive products of metabolism, possibly arising from a rearrangement of putative epoxide intermediates. We synthesized the enedial derivative of teucrin A as well as the enedial derived from a model furan, 3-(4-methoxy-benzyloxymethyl)-furan, by dimethyldioxirane oxidation and characterized the products of their reactions with amino acids and peptides. The reactions of the model enedial, 2-(4-methoxy-benzyloxymethyl)-but-2-enedial,withN-acetyl lysine (NAL) afforded regioisomeric N-alkyl-3-pyrrolin-2-ones, differing in the substitution on the double bond of the heterocyclic ring. Novel products formed in the reactions of the model enedial with N-acetyl cysteine (NAC) and both NAC/NAL uncovered the existence of tautomerization between the enedial and a hydroxyenal, which was manifest by the loss of 4-methoxybenzylalcohol and the incorporation of a second molecule of NAC. The reactions of teucrin A-enedial with NAC and NAL afforded analogues of the products observed with the model enedial, and the existence of the tautomeric equilibrium resulted in epimerization of the proton (H12) adjacent to the former furan ring. This work further illuminates the complex chemical behavior of unsaturated dialdehydes as an important class of toxic metabolites and lays the foundation for studies of the protein targets of teucrin A-enedial.

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Reference:
Pyrroline – Wikipedia,
,1-Pyrroline | C4H7N – PubChem

02/9/2021 News Why Are Children Getting Addicted To C15H11NO3

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Experimental and Computational Study of the 1,5-O -> N Carbamoyl Snieckus-Fries-Type Rearrangement

The reactions of o-lithiated O-aryl N,N-diethylcarbamates with different C-N multiple bond electrophiles have been thoroughly studied. A 1,5-O -> N carbamoyl shift, a new variation of the anionic Fries-type rearrangement, takes place when nitriles, imines, or alkylcarbodiimides are employed. In these cases, the carbamoyl group plays a dual role as a directing group, building up a variety of functional groups through the 1,5-O -> N carbamoyl migration. On the other hand, the use of iso(thio)cyanates and arylcarbodiimides led to non-rearranged o-functionalized O-arylcarbamates. This reactivity was further computationally explored, and the governing factor could be traced back to the relative basicity of the alternative products (migrated vs nonmigrated substrates). This exploration also provided interesting insights about the degree of complexation of the lithium cations onto these substrates. A new access to useful 2-hydroxybenzophenone derivatives has also been developed.

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Pyrroline – Wikipedia,
,1-Pyrroline | C4H7N – PubChem

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Three-component reaction between ethyl N-(4-oxo-2-thioxothiazolidin-3-yl)oxalamate and acetylenic esters in the presence of triphenylphosphine

N-aminorhodanine reacts with ethyl chlorooxoacetate in ethanol to produce ethyl N-(4-oxo-2-thioxothiazolidin-3yl) oxalamate in nearly quantitative yield. Reaction between this adduct and electron-deficient acetylenic esters in the presence of triphenylphosphine leads to dialkyl 4-ethoxy-5-oxo-1-(4-oxo-2-thioxothiazolidin-3-yl)-2,5-dihydro-1H-pyrrole-2,3-dicarboxylate derivatives in good yields.

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What I Wish Everyone Knew About 2-(9-Oxoacridin-10(9H)-yl)acetic acid

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Tautomerism and regioselectivity of the protonation of 2-pyrrolidone. Stereoselectivity of complexation between palladium(II), chloride ion, and 2-pyrrolidone

According to the AM1, PM3, HF/6-31G(d,p), and MP2/6-31G(d,p)//HF/6-31G(d,p) calculations, it is the lactam tautomer of 2-pyrrolidone that is thermodynamically most stable in both the gas phase and an aqueous solution. Analysis of the PM3 data with consideration of the medium showed that the tautomeric equilibrium of 2-pyrrolidone (pyrroline-2-ol) in aqueous solution is shifted to the lactim form, which thus can be involved in complexation with palladium(II). 2-Pyrrolidone was found to be protonated at the O atom in both the gas phase and aqueous solution, in agreement with the concept of the mesomeric displacement of the electron density in the amide fragment. The aqueous medium stabilizes the lactim tautomer of 2-pyrrolidone more strongly than the lactam tautomer and the O-protonated cyclic amide than the N-protonated one. The stereoselectivity of complexation between palladium(II), chloride ion, and pyrroline-2-ol was explained. The initially formed tetragonal-pyramidal adduct with an axial organic ligand undergoes rearrangement into an intermediate with an extra axial Cl atom, which is a precursor of the cis-product. The thermodynamically less stable cis-isomer of the complex [PdCl2(pyrrolin-2-ol)(2)] is formed from the thermodynamically most favorable intermediate in associative nucleophilic substitution. At the supramolecular level, the cis-product can be stabilized by intermolecular dipole-dipole association in the crystal.

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,1-Pyrroline | C4H7N – PubChem

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SYNTHESIS OF NITROXIDE CONTAINING POLYENES – 2 CHEMICALLY-MODIFIED RETINALS AND THEIR INTERACTION WITH BACTERIORHODOPSIN

The synthesis and spectroscopic characterization of two retinal analogues is described, the paramagnetic 3-pyrrolin-1-yloxy analogue 1 and its diamagnetic equivalent, the 3-pyrroline analogue 2. Various aspects of the synthesis of the aminoxy group containing polyenes are discussed. Upon interaction with bacterioopsin, both 1 and 2 are incorporated in the protein and form a system with lambda(max) 459 nm. Neither of the two bacteriorhodopsin analogues is photoactive. ESR spectroscopy data of the system containing 1 show that the ring part of the chromophore in the protein is rigidly fixed in orientation.

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,1-Pyrroline | C4H7N – PubChem

Chemical Properties and Facts of 2-(9-Oxoacridin-10(9H)-yl)acetic acid

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Magnetic cobalt ferrite nanoparticles functionalized with citric acid as a green nanocatalyst for one-pot three-component sonochemical synthesis of substituted 3-pyrrolin-2-ones

A clean, convenient and facile approach for one-pot ultrasonic assisted synthesis of substituted 3-pyrrolin-2-ones from diethyl acetylenedicarboxylate, aniline and aldehyde derivatives is described. The reactions were carried out in the presence of an efficient, green and reusable acidic nanocatalyst, magnetic cobalt ferrite nanoparticles functionalized with citric acid (CoFe2O4@CA), with high yields under mild conditions. Also, use of ultrasound irradiation made this approach an attractive protocol for the synthesis of these products. The method has been successful in achieving the green chemistry objective. An energy efficient protocol using ultrasound irradiation instead of conventional heating or stirring and use of ethanol as a non-hazardous, inexpensive and green solvent in the one-step reaction against sequential reaction steps thus combining the features of both economic and environmental advantages. [GRAPHICS] .

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Synthetic Study on Acremoxanthone A, Part 2: Model Study on the EFG Xanthone Moiety through a Nitrile Oxide Cycloaddition-SNAr Sequence

Toward a total synthesis of acremoxanthone A, we report a model study on the construction of the EFG ring system. The key steps include (1) an intermolecular 1,3-dipolar cycloaddition of an aryl nitrile oxide with a dienone, and (2) an SNAr reaction for construction of the F ring.

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Reference:
Pyrroline – Wikipedia,
,1-Pyrroline | C4H7N – PubChem