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Relevant academic research and scientific papers

Synthesis of Benz-Fused Azoles via C-Heteroatom Coupling Reactions Catalyzed by Cu(I) in the Presence of Glycosyltriazole Ligands

Glycosyl triazoles are conveniently accessible and contain multiple metal-binding units that may assist in metal-mediated catalysis. Azide derivatives of d-glucose have been converted to their respective aryltriazoles and screened as ligands for the synthesis of 2-substituted benz-fused azoles and benzimidazoquinazolinones by Cu-catalyzed intramolecular Ullmann type C-heteroatom coupling. Good to excellent yields for a variety of benz-fused heterocyles were obtained for this readily accessible catalytic system.

Method for synthesizing benzothiazole by microwave radiation of benzothioamide compound in aqueous phase

The invention discloses a method for synthesizing benzothiazole by microwave radiation of a benzothioamide compound in an aqueous phase. The method includes the steps: adding the benzothioamide compound into the aqueous phase under microwave conditions; performing cyclization under alkaline conditions to generate the benzothiazole. The method for preparing the benzothiazole is environmentally friendly, simple and convenient in operation, safe, cheap and efficient. Compared with the prior art, the method is applicable to a lot of functional groups, high in yield, few in by-products, simple in operation, safe, low in cost and environmentally friendly.

Method used for rapid preparation of benzo-heterocycle compound with physical grinding under solvent-free room temperature conditions

The invention discloses a method used for rapid preparation of benzo-heterocycle compound with physical grinding under solvent-free room temperature conditions. According to the method, glacial aceticacid is taken as a catalyst; at solvent-free room temperature conditions, physical grinding is adopted, reaction of 2-substituted arylamines (2-mercapto arylamine, 2-aminophenol, and o-phenylenediamine) and aromatic aldehydes is carried out using physical grinding. The method is friendly to the environment, is simple in operation, is safe, is low in cost, and is high in efficiency. Compared withthe prior art, the advantages are that: the method is suitable for a large amount of functional groups, yield is high, less by-product is generated, operation is simple, the method is safe, cost is low, and the method is friendly to the environment.

KI-catalyzed arylation of benzothiazoles from the coupling of aryl aldehydes with benzothiazoles in neat water

A KI-catalyzed oxidative coupling of benzothiazoles with aryl aldehydes has been developed using TBHP as an oxidant in neat water under metal free conditions. Various 2-aryl benzothiazoles were prepared in 36-79% yields for 28 examples. The mechanistic studies suggested that this transformation proceeded via a radical process. The Royal Society of Chemistry.

Alumina as a support and catalyst for the synthesis of benzothiazoles in solvent-free condition

Arylbenzothiazole (4) and benzothiazolylcoumarins (5) were prepared by the condensation of 2-aminothiophenol (1) and hydroxybenzaldehydes (2) and 3-ethoxycarbonylcoumarinnin (3), respectively, in solvent- free condition. Of the solid support used,γ-Al2O3 demonstrated the best activity. Alinear regression line obtained from correlation between relative formation rate and Hammett constants with slope of 0.653 suggested that this condensation process is less sensitive to the substituents on the phenyl ring due to low efficacy of polarization in the solid state. In general, good yields (>80% yield) were obtained for the formation of 4. Conversely, yields of 5 were poor, because of γ-Al2O3 catalytic decomposition of 3 to form 2 (without P2O5) and coumarin (with P2O5).

Weinreb amide as an efficient reagent in the one pot synthesis of benzimidazoles and benzothiazoles

One pot synthesis of 2-substituted benzimidazoles/benzothiazoles through condensation is followed by cyclization of Weinreb amide with o-diaminoarene or o-aminothiophenol is reported. In the presence of boron trifluoride etherate in 1,4-dioxane solvent, a high yield (75-94%) was achieved within 60 min. Weinreb amide shows high selectivity in the reaction, even in presence of other active functional groups such as carboxyl, halogen, cyano, and methoxy.

Nickel-catalyzed C-H arylation of azoles with haloarenes: Scope, mechanism, and applications to the synthesis of bioactive molecules

Novel nickel-based catalytic systems for the C-H arylation of azoles with haloarenes and aryl triflates have been developed. We have established that Ni(OAc)2/bipy/LiOtBu serves as a general catalytic system for the coupling with aryl bromides and iodides as aryl electrophiles. For couplings with more challenging electrophiles, such as aryl chlorides and triflates, the Ni(OAc)2/dppf (dppf=1,1′-bis(diphenylphosphino)ferrocene) system was found to be effective. Thiazoles, benzothiazoles, oxazoles, benzoxazoles, and benzimidazoles can be used as the heteroarene coupling partner. Upon further investigation, we discovered a new protocol for the present coupling using Mg(OtBu)2 as a milder and less expensive alternative to LiOtBu. Attempts to reveal the mechanism of this nickel-catalyzed heterobiaryl coupling are also described. This newly developed methodology has been successfully applied to the syntheses of febuxostat (a xanthine oxidase inhibitor that is effective for the treatment of gout and hyperuricemia), tafamidis (effective for the treatment of TTR amyloid polyneuropathy), and texaline (a natural product having antitubercular activity). Copyright

One-pot tandem approach for the synthesis of benzimidazoles and benzothiazoles from alcohols

Propylphosphonic anhydride (T3P) has been demonstrated to be an efficient and mild reagent for the one-pot synthesis of benzimidazoles and benzothiazoles from variety of alcohols. Mild conditions, short reaction time, broad functional group tolerance, low epimerization, easy and quick isolation of the products, excellent chemo selectivity, and excellent yields are main advantages of this procedure. Thus, the present method is utilizing alcohols instead of aldehydes.

1-Methyl-2-pyrrolidinone: A Well-Adapted Solvent in the Benzothiazoles Synthesis

We describe the synthesis of a series of 2-aryl and 2-alkyl benzothiazoles with high yields using 1-methyl-2-pyrrolidinone as reaction solvent.