Month: April 2022

Application In Synthesis of 2-(Pyridin-4-yl)-1H-benzo[d]imidazole. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 2-(Pyridin-4-yl)-1H-benzo[d]imidazole, is researched, Molecular C12H9N3, CAS is 2208-59-5, about Dependence of acute toxicity on structure in a series of 2-substituted benzimidazoles. Author is Lebedeva, M. N.; Kolosova, M. I.; Gladkikh, V. F.; Lychko, N. D..

A comparison of the acute toxicities of 52 benzimidazoles (I) in mice indicated that single substitution at position 2, especially with o-bromophenyl, o-, m-, or p-chlorophenyl, and o-aminophenyl, decreased toxicity ≥10-fold, whereas substitution also at position 5(6) or 1 increased toxicity. Of the 18 2-aryl substituted I, H-620 (I, R = o-aminophenyl, R1 = R2 = H) [5805-39-0] was the least toxic; H-728 (I, R = o-chlorophenyl, R1 = CO2Me, R2 = H) [34675-55-3] was most toxic. Of the 13 2-heteryl substituted I, H-725 (I, R = α-piperidyl, R1 = COMe, R2 = H) [34675-57-5] was least toxic; H-582 (I, R = γ-pyridyl, R1 = R2 = H) [2208-59-5] was most toxic. Of the 21 2-amino substituted I, H-738 (I, R = NHCOMe, R1 = R2 = H) [21202-05-1] was least toxic; H-658 (I, R = piperidyl, R1 = R2 = H) [2851-12-9] was most toxic.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Reference of 1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene, is researched, Molecular C21H24N2, CAS is 141556-42-5, about Oligomerization of phosphaalkynes mediated by bulky N-heterocyclic carbenes: avenues to novel phosphorus frameworks.

Reactions of RCP (R = tBu or Ad (adamantyl)) with NHCs (SIMes, 1a; IMes, 1b and IDipp, 1d), leading to 1,2,3-triphosphetenes 2 and 3, a triphosphole 4, and a di-1,2-dihydro-1,2-diphosphete-substituted diphosphene 5, are reported. Compound 5 represents a novel P6 chain framework, as well as a newly discovered phosphaalkyne hexamer stabilized by two NHCs. Computational investigations suggest that the weak π-accepting ability of NHCs results in low stability of the initially formed 2H-phosphirenes, thus facilitating spontaneous oligomerization reactions. Such oligomerizations are highly susceptible to the electronic property and steric bulk of NHCs.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Zheng, Songlin; Chen, Zimin; Hu, Yuanyuan; Xi, Xiaoxiang; Liao, Zixuan; Li, Weirong; Yuan, Weiming published an article about the compound: Nickel(II) chloride ethylene glycol dimethyl ether complex( cas:29046-78-4,SMILESS:COCCOC.Cl[Ni]Cl ).Computed Properties of C4H10Cl2NiO2. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:29046-78-4) through the article.

A highly chemo- and regioselective intermol. 1,2-aryl-aminoalkylation of alkenes by photoredox/nickel dual catalysis is described here. This three-component conjunctive cross-coupling is highlighted by its first application of primary alkyl radicals, which were not compatible in previous reports. The readily prepared α-silyl amines could be transferred to α-amino radicals by photo-induced single electron transfer step. The radical addition/cross-coupling cascade reaction proceeds under mild, base-free and redox-neutral conditions with good functional group tolerance, and importantly, provides an efficient and concise method for the synthesis of structurally valuable α-aryl substituted γ-amino acid derivatives motifs.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 2-Phenylpyridine, is researched, Molecular C11H9N, CAS is 1008-89-5, about Deliberately Losing Control of C-H Activation Processes in the Design of Small-Molecule-Fragment Arrays Targeting Peroxisomal Metabolism.Quality Control of 2-Phenylpyridine.

1-Biphenylylpyrrolidones,and 2-biphenylyl- and 2-terphenylylpyridines were prepared by photochem. arylation of 1-arylpyrrolidones and 2-arylpyridines with arenediazonium tetrafluoroborates. Combined photochem. arylation, “”nuisance effect”” (SNAr) reaction sequences have been employed in the design of small arrays for immediate deployment in medium-throughput X-ray protein-ligand structure determination Reactions were deliberately allowed to run “”out of control”” in terms of selectivity; for example the ortho-arylation of 2-phenylpyridine gave five products resulting from mono- and bisarylations combined with SNAr processes. As a result, a number of crystallog. hits against NUDT7, a key peroxisomal CoA ester hydrolase, have been identified.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Formula: C21H14Br4O5S. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 3,3-Bis(3,5-dibromo-4-hydroxy-2-methylphenyl)-3H-benzo[c][1,2]oxathiole 1,1-dioxide, is researched, Molecular C21H14Br4O5S, CAS is 76-60-8, about Intracellular prostaglandin E2 contributes to hypoxia-induced proximal tubular cell death. Author is Garcia-Pastor, Coral; Benito-Martinez, Selma; Bosch, Ricardo J.; Fernandez-Martinez, Ana B.; Lucio-Cazana, Francisco J..

Proximal tubular cells (PTC) are particularly vulnerable to hypoxia-induced apoptosis, a relevant factor for kidney disease. We hypothesized here that PTC death under hypoxia is mediated by cyclo-oxygenase (COX-2)-dependent production of prostaglandin E2 (PGE2), which was confirmed in human proximal tubular HK-2 cells because hypoxia (1% O2)-induced apoptosis (i) was prevented by a COX-2 inhibitor and by antagonists of prostaglandin (EP) receptors and (ii) was associated to an increase in intracellular PGE2 (iPGE2) due to hypoxia-inducible factor-1α-dependent transcriptional up-regulation of COX-2. Apoptosis was also prevented by inhibitors of the prostaglandin uptake transporter PGT, which indicated that iPGE2 contributes to hypoxia-induced apoptosis (on the contrary, hypoxia/reoxygenation-induced PTC death was exclusively due to extracellular PGE2). Thus, iPGE2 is a new actor in the pathogenesis of hypoxia-induced tubular injury and PGT might be a new therapeutic target for the prevention of hypoxia-dependent lesions in renal diseases.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene, is researched, Molecular C21H24N2, CAS is 141556-42-5, about Acyl Donor Intermediates in N-Heterocyclic Carbene Catalysis: Acyl Azolium or Azolium Enolate?.Related Products of 141556-42-5.

Azolium enolates and acyl azolium cations have been proposed as intermediates in numerous N-heterocyclic carbene (NHC) catalyzed transformations. Acetyl azolium enolates were generated from the reaction of 2-propenyl acetate with both saturated (SIPr) and aromatic (IPr) NHCs, isolated, and characterized (NMR, XRD). Protonation with triflic acid gave the corresponding acetyl azolium triflates which were isolated and characterized (NMR, XRD). Acyl azolium cations have been proposed as immediate precursors of the ester product, for example, in the redox esterification of α,β-enals. Studies with d3-acetyl azolium triflate suggest that ester formation originates instead from an azolium enolate intermediate. Furthermore, the acetyl azolium enolate selectively reacted with alc. nucleophiles in the presence of amines. While the acetyl azolium cation did not react with alcs., an ester-selective reaction was induced by addition of base, by intermediate formation of the acetyl azolium enolate.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Hauser, Philipp M.; van der Ende, Melita; Groos, Jonas; Frey, Wolfgang; Wang, Dongren; Buchmeiser, Michael R. published an article about the compound: 1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene( cas:141556-42-5,SMILESS:CC1=CC(C)=CC(C)=C1[N+]2=[C-]N(C3=C(C)C=C(C)C=C3C)C=C2 ).Product Details of 141556-42-5. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:141556-42-5) through the article.

The first cationic and neutral tungsten alkylidyne N-heterocyclic carbene (NHC) complexes bearing one triflate ligand were synthesized and tested for their reactivity in alkyne metathesis. Both types of tungsten alkylidyne complexes display a higher productivity in alkyne metathesis than the analogous neutral tungsten alkylidyne NHC trisalkoxide complexes. Reaction of W( CC6H4OMe)(1,3-bis(1-hydroxy-1,1-trifluoromethylethyl)-imidazol-2-ylidene)Cl (W18) with AgB(ArF)4 (ArF = 3,5-bis(trifluoromethyl)phenyl) resulted in the unexpected formation of, to the best of our knowledge, the first cationic ditungstatetrahedrane W2(1,3-bis(1-hydroxy-1,1-trifluoromethyl-ethyl)-imidazol-2-ylidene)2(MeCN)(μ-((Ar)CC(Ar)))+ (B(ArF)4)- (W19, Ar = C6H4OMe), which suggests bimol. decomposition as a possible decomposition pathway of cationic tungsten alkylidyne NHC complexes. Reaction of the cationic tungsten alkylidyne NHC complex W( CC6H4OMe)(1,3-diisopropylimidazol-2-ylidene)(OC(CF3)2Me)2(NCtBu)+ (B(ArF)4)- (W7) with 1-phenyl-1-propyne allowed for the isolation of a cationic tungstacyclobutadiene W(C3(Ph)(Me)(C6H4OMe))(1,3-diisopropylimidazol-2-ylidene)(OC(CF3)2Me)2(NCtBu)+ (B(ArF)4)- (W20). Its formation strongly supports a cationic active species in the alkyne metathesis with tungsten alkylidyne NHC complexes.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Category: indole-building-block. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: Bis((S)-4-phenyl-4,5-dihydrooxazol-2-yl)methane, is researched, Molecular C19H18N2O2, CAS is 132098-59-0, about Enoldiazosulfones for Highly Enantioselective [3 + 3]-Cycloaddition with Nitrones Catalyzed by Copper(I) with Chiral BOX Ligands.

Enoldiazosulfones undergo [3 + 3]-cycloaddition with nitrones when catalyzed by copper(I) catalysts, but not with dirhodium(II) catalysts. Under mild reaction conditions with chiral bisoxazoline ligands, copper(I) catalysts produce 1,2-oxazine-sulfone derivatives in high yields and enantioselectivities. Dirhodium(II) catalysts form stable donor-acceptor cyclopropenes that undergo uncatalyzed [3 + 2]-cycloaddition reactions with nitrones.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Related Products of 132098-59-0. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: Bis((S)-4-phenyl-4,5-dihydrooxazol-2-yl)methane, is researched, Molecular C19H18N2O2, CAS is 132098-59-0, about Iron-catalysed enantioconvergent Suzuki-Miyaura cross-coupling to afford enantioenriched 1,1-diarylalkanes. Author is Tyrol, Chet C.; Yone, Nang S.; Gallin, Connor F.; Byers, Jeffery A..

The first stereoconvergent Suzuki-Miyaura cross-coupling reaction was developed to afford enantioenriched 1,1-diarylalkanes I [R = Me, Et, i-Pr, etc.; R1 = Ph, 4-FC6H4, 1-naphthyl, etc.; R2 = Ph, 4-MeC6H4, 2-naphthyl, etc.]. An iron-based complex containing a chiral cyanobis(oxazoline) ligand framework was best to obtain enantioenriched 1,1-diarylalkanes from cross-coupling reactions between unactivated aryl boronic esters and benzylic chlorides. Enhanced yields were obtained when 1,3,5-trimethoxybenzene was used as an additive, which was hypothesized to extend the lifetime of the iron-based catalyst. Exceptional enantioselectivities were obtained with challenging ortho-substituted benzylic chlorides.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Computed Properties of C19H18N2O2. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: Bis((S)-4-phenyl-4,5-dihydrooxazol-2-yl)methane, is researched, Molecular C19H18N2O2, CAS is 132098-59-0, about Enantiotopic Differentiation of pro-R or pro-S Chlorides in (Dichloromethyl)borates by Chiral Lewis Acids: Enantioselective Synthesis of (α-Chloroalkyl)boronates. Author is Jadhav, Prabhakar K.; Man, Hon-Wah.

The 1,2-migration reaction of an alkyl group in borate complexes, I (e.g. R = Bu), derived from dichloromethyl pinacol boronates and alkyllithium was catalyzed by chiral Lewis acids capable of enantiotopic differentiation of Pro (R) or Pro (S) chloride groups on an sp3 C center. It takes place with an enantiomeric ratio of 94:6 to provide α-chloroalkylboronates, II, in 70-75% chem. yields. Chiral Lewis acids examined in this study were prepared in situ from ZnEt2, Yb(OTf)3, Cu(OTf)2, Zn(OTf)2 or Lu(OTf)3 and chiral ligands including amino alcs. and bisoxazolines. Highest enantioselectivity (88% ee) was observed with the chiral Lewis acid derived from Yb(OTf)3 and bisoxazoline III. This is the 1st example of a chiral Lewis acid catalyzed enantioselective 1,2-migration reaction of dichloromethylborate complexes.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles