Day: April 2, 2022

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 4360-63-8, is researched, Molecular C4H7BrO2, about Modular Synthesis of Bicyclic and Tricyclic (Aza-) Arenes from Nucleophilic (Aza-)Arenes with Electrophilic Side Arms via [4+2] Annulation Reactions, the main research direction is bicyclic aza arene preparation; tricyclic aza arene preparation; enolizable carbonyl compound aza arene annulation scandium triflate catalyst.Name: 2-Bromomethyl-1,3-dioxolane.

An efficient strategy for the synthesis of bicyclic aza-arenes I [R1 = Me, Ph, 2-thienyl, etc.; R2 = Me, OEt, OBn, etc.; Ar = OMe, Cl, Ph, etc.] and tricyclic aza-arenes, e.g., II from a nucleophilic aza-arene with an electrophilic side arm was developed. The aza-arene precursor had both nucleophilic and electrophilic sites, which were fixed at a 1,4-distance. The bicyclic and tricyclic (aza-)arene products I and II were constructed via [4+2] annulation by using scandium(III) triflate as a catalyst and enolizable ketones or aldehydes as the counterpart reagents. A variety of six-membered carbocycles and heterocycles, such as indolizines, indoles, naphthalenes, carbazoles and pyrido[1,2-α]indoles, were successfully synthesized. Some one-pot sequential reactions were also developed, in which the 1,4-donor-acceptor precursors can be synthesized via oxidation of alcs. or a proper condensation reaction.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called N-Cyanation of Primary and Secondary Amines with Cyanobenziodoxolone (CBX) Reagent, published in 2021-10-25, which mentions a compound: 7524-52-9, mainly applied to cyanamide preparation; amine cyanobenziodoxolone electrophilic cyanation; N-cyanation; amines; cyanamides; cyanobenziodoxolone; electrophilic cyanation, SDS of cas: 7524-52-9.

An efficient electrophilic N-cyanation of amines e.g., pyrrolidine with a stable and less-toxic 1-cyano-1,2-benziodoxol-3-(1H)-one reagent towards the synthesis of cyanamides e.g., Pyrrolidine-1-carbonitrile was disclosed. This synthetically practicable strategy allows the construction of a wide variety of cyanamides under very mild and simple conditions with a broad functional group compatibility, and showcases a huge potential in late-stage modification of complex mols.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

HPLC of Formula: 707-61-9. 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: 4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxide, is researched, Molecular C11H13OP, CAS is 707-61-9, about Catalytic aza-Wittig Cyclizations for Heteroaromatic Synthesis. Author is Marsden, Stephen P.; McGonagle, Alison E.; McKeever-Abbas, Ben.

The first examples of heterocycle synthesis by iminophosphorane formation/intramol. aza-Wittig cyclizations that are catalytic in the organophosphorus component are reported. The reaction has been demonstrated in the synthesis of both azine (phenanthridine) and azole (benzoxazole) heterocycles. E.g., in presence of phospholene oxide I, reaction of isocyanate 2-OCNC6H4C6H4CO2Me-2, formed from acyl azide 2-N3COC6H4C6H4CO2Me-2 by Curtius rearrangement, gave 71% phenanthridine II. Catalyst loadings down to 1 mol % have been used with little or no loss in reaction efficiency. The intimate involvement of the phosphine oxide in the catalytic cycle has been verified by in situ IR spectroscopy.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: H-Trp-OMe.HCl, is researched, Molecular C12H15ClN2O2, CAS is 7524-52-9, about Synthesis of C-mannosylated glycopeptides enabled by Ni-catalyzed photoreductive cross-coupling reactions, the main research direction is mannosylated glycopeptide synthesis solvent effect; nickel catalyzed photoreductive cross coupling reaction mechanism anomerization; insect hormone solid phase peptide syntheses glycopeptide epitope antibody.Category: dioxole.

The biol. functions of tryptophan C-mannosylation are poorly understood, in part, due to a dearth of methods for preparing pure glycopeptides and glycoproteins with this modification. To address this issue, efficient and scalable methods are required for installing this protein modification. Here, we describe unique Ni-catalyzed cross-coupling conditions that utilize photocatalysis or a Hantzsch ester photoreductant to couple glycosyl halides with (hetero)aryl bromides, thereby enabling the α-C-mannosylation of 2-bromo-tryptophan, peptides thereof, and (hetero)aryl bromides more generally. We also report that 2-(α-D-mannopyranosyl)-L-tryptophan undergoes facile anomerization in the presence of acid: something that must be considered when preparing and handling peptides with this modification. These developments enabled the first automated solid-phase peptide syntheses of C-mannosylated glycopeptides, which we used to map the epitope of an antibody, as well as providing the first verified synthesis of Carmo-HrTH-I, a C-mannosylated insect hormone. To complement this approach, we also performed late-stage tryptophan C-mannosylation on a diverse array of peptides, demonstrating the broad scope and utility of this methodol. for preparing glycopeptides.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 2-Bromomethyl-1,3-dioxolane(SMILESS: BrCC1OCCO1,cas:4360-63-8) is researched.Category: chiral-oxygen-ligands. The article 《Modular Synthesis of Bicyclic and Tricyclic (Aza-) Arenes from Nucleophilic (Aza-)Arenes with Electrophilic Side Arms via [4+2] Annulation Reactions》 in relation to this compound, is published in Advanced Synthesis & Catalysis. Let’s take a look at the latest research on this compound (cas:4360-63-8).

An efficient strategy for the synthesis of bicyclic aza-arenes I [R1 = Me, Ph, 2-thienyl, etc.; R2 = Me, OEt, OBn, etc.; Ar = OMe, Cl, Ph, etc.] and tricyclic aza-arenes, e.g., II from a nucleophilic aza-arene with an electrophilic side arm was developed. The aza-arene precursor had both nucleophilic and electrophilic sites, which were fixed at a 1,4-distance. The bicyclic and tricyclic (aza-)arene products I and II were constructed via [4+2] annulation by using scandium(III) triflate as a catalyst and enolizable ketones or aldehydes as the counterpart reagents. A variety of six-membered carbocycles and heterocycles, such as indolizines, indoles, naphthalenes, carbazoles and pyrido[1,2-α]indoles, were successfully synthesized. Some one-pot sequential reactions were also developed, in which the 1,4-donor-acceptor precursors can be synthesized via oxidation of alcs. or a proper condensation reaction.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Related Products of 707-61-9. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxide, is researched, Molecular C11H13OP, CAS is 707-61-9, about Phospho sugars; novel preparation and their glycosyl compounds. Author is Ikai, Koichi; Iida, Akihito; Yamashita, Mitsuji.

Treatment of 1-phenyl-2-, and -3-phospholene 1-oxides with NBS affords 4-bromo-1-phenyl-2-phospholene 1-oxide (I). Substitution of the bromide with acetate, followed by stereoselective oxidation with osmium tetroxide and peracetylation with acetic anhydride/pyridine affords phospho sugar derivatives II of tetrafuranose. Furthermore, glycosyl compounds III (R = iodo, OAc, SCN, N3) of phospho sugars were prepared from 3-methyl-1-phenyl-2-phospholene 1-oxide by bromination and nucleophilic substitution reactions.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《2- and 5-Fluoronicotinic acids》. Authors are Beaty, R. D.; Musgrave, W. K. R..The article about the compound:Methyl 5-fluoro-3-pyridinecarboxylatecas:455-70-9,SMILESS:COC(=O)C1=CC(F)=CN=C1).Name: Methyl 5-fluoro-3-pyridinecarboxylate. Through the article, more information about this compound (cas:455-70-9) is conveyed.

5-Aminonicotinic acid (I) (3 g.) in 20 cc. 40% HBF4 at -5° treated with 2.5 g. NaNO2, the mixture kept 1 h., heated 30 min. at 50°, neutralized with Na2CO3, and the resulting salt refluxed 2-3 h. with 3% MeOH-H2SO4, gives 0.3 g. Me 5-fluoronicotinate, m. 48°. The 2-isomer of I (2 g.) in 10 cc. 40% HBF4, diazotized with 1 g. NaNO2 in 10 cc. H2O at 0 to -5°, and the solution kept 1 h. at 0°, heated 1 h. at 50-60°, and basified to pH 5 with NaOH, gives 33% 2-fluoronicotinic acid, m. 164-5°; the Me ester m. 74-5° and the amide m. 124°. 3-Fluoropicolinic acid could not be prepared by this method.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 5-(11bR)-Dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-yl-5H-dibenz[b,f]azepine(SMILESS: N1(P2OC3=CC=C4C=CC=CC4=C3C5=C6C=CC=CC6=CC=C5O2)C7=CC=CC=C7C=CC8=CC=CC=C81,cas:1265884-98-7) is researched.Name: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole. The article 《Total Synthesis of Taiwaniadducts B, C, and D》 in relation to this compound, is published in Journal of the American Chemical Society. Let’s take a look at the latest research on this compound (cas:1265884-98-7).

The first total syntheses of taiwaniadducts B, C, and D have been accomplished. Two diterpenoid segments [trans-ozic Me ester (I) and II] were prepared with high enantiopurity, both through Ir-catalyzed asym. polyene cyclization. A sterically demanding I + II intermol. Diels-Alder reaction promoted by Er(fod)3 assembled the scaffold of taiwaniadducts B and C. A carbonyl-ene cyclization forged the cage motif of taiwaniadduct D at a late stage, providing over 200 mg of this compound

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Nija, B.; Rasheed, Arun; Kottaimuthu, A. published the article 《Development, characterization and pharmacological evaluation of amino acid prodrugs of (+)-Ibuprofen》. Keywords: Ibuprofen amino acid prodrug pharmacol evaluation.They researched the compound: H-Trp-OMe.HCl( cas:7524-52-9 ).Reference of H-Trp-OMe.HCl. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:7524-52-9) here.

The current research work investigate the neuronal pathway associated with NSAIDs that lead to the reduction in the initiation and progression of neurodegenerative diseases such as Alzheimer’s disease, Parkinsonism, etc. This research was developed amino acid prodrugs of the active enantiomer of ibuprofen, (+)-IBN and checks the pharmacol. effects, neuroprotective effect, anti inflammatory effect and anti-ulcerogenic effect. The treatment using (+)-IBN reduced the action of micoglia and the release of cytokine especially TNFα that are mainly involved in the neurodegenerative process. (+)- IBN reduced the deposition of soluble beta amyloid plaque by inhibiting the amyloid precursor protein, beta-secretase 1 and also enhancing the degradation process of beta amyloid via induction of insulin degrading enzyme. (+)-IBN also showed the property that the reduction in the TAU misfolding process. Therefore, the synthesized (+)-IBN amino acid prodrugs treatment effectively produce neuroprotective action, both restoring memory realed risk factors and reversing multiple brain neuropathol. hallmarks. The current research study developed the three amino acid prodrugs of (+)-ibuprofen by conjugating with L-Ph alanine, L-tryptophan and L-tyrosine also the physico-chem. characterization and spectral characterization was done. This study modify the carboxylic acid functional group present in the NSAIDs that lead to the formation of prodrugs with enhanced anti-inflammatory activity, reduced side effects and protective effect against neurodegenerative processes.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: H-Trp-OMe.HCl( cas:7524-52-9 ) is researched.Safety of H-Trp-OMe.HCl.Chan, Hwai-Chien; Bueno, Bianca; Le Roch, Adrien; Gagnon, Alexandre published the article 《Copper-promoted N-arylation of the imidazole side chain of protected histidine by using triarylbismuth reagents》 about this compound( cas:7524-52-9 ) in Chemistry – A European Journal. Keywords: dipeptide arylated histidine synthesis functional group; histidine imidazole arylation copper catalyst triarylbismuth reagent; arylation reaction mechanism; N-arylation; copper catalysis; histidine; imidazole; organobismuthines. Let’s learn more about this compound (cas:7524-52-9).

The N-arylation of the side chain of histidine by using triarylbismuthines is reported. The reaction is promoted by copper(II) acetate in dichloromethane at 40°C under oxygen in the presence of diisopropylethylamine and 1,10-phenanthroline and allows the transfer of aryl groups with substituents at any position of the aromatic ring. The reaction shows excellent functional group tolerance and is applicable to dipeptides where the histidine is located at the N terminus. A histidine-guided backbone N-H arylation was observed in dipeptides where the histidine occupies the C terminus.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem