32586-68-8

Upstream product

• 134174-55-3 zinc 2-aminobenzeneselenolate 
• 98-88-4 benzoyl chloride 
• 462-80-6 benzyne 
• 19768-00-4 3,4-Diphenyl-1,2,5-selenadiazole 
• 70086-67-8 2-(methylselanyl)aniline 
• 61053-50-7 methyl(2-nitrophenyl)selenide 
• 63870-44-0 bis(2-aminophenyl)diselenide 
• 100-52-7 benzaldehyde 
• 615-43-0 2-iodophenylamine 
• 15310-02-8 o-iodobenzanilide 
• 103-82-2 phenylacetic acid 
• 100-44-7 benzyl chloride 
• 88-73-3 2-Chloronitrobenzene 
• 611-73-4 Benzoylformic acid 

Downstream Products

• 750839-91-9 (2-phenylbenzo-1,3-selenazole)trifluoroboron 

Relevant academic research and scientific papers

Copper(I)-catalyzed highly efficient synthesis of benzoselenazoles and benzotellurazoles

(Chemical Equation Presented) A simple and practical useful synthetic method of 1,3-benzoselenazoles having a heteroatom substituent such as NRR', OR, and SR groups at the 2-position was developed by the copper(I)-catalyzed reaction of 2-bromophenyl (1) o

Ground and excited-state properties of 1,3-benzoselenazole derivatives: A combined theoretical and experimental photophysical investigation

A series of 1,3-benzoselenazole derivatives were prepared with different substituents by complementary methodologies starting from aldehydes or carboxylic acids, using sodium metabisulfite and tributylphosphine, respectively, according to the substituent

Facile preparation of 2-arylbenzoselenazoles from three components reactions: 2-Chloronitrobenzene, Se, and arylacetic acids

A selenium-mediated decarboxylative cyclization of 2-chloronitrobenzene and arylacetic acids to prepare 2-arylbenzoselenazoles has been established under metal-free condition. The reactions proceeded in moderate to good yields with good functional toleran

Se-mediated one-pot synthesis of 2-substituted benzoselenazole derivatives from 2 to iodoanilines and arylacetic acids/arylmethyl chlorides

A general approach to the formation of 2-substituted benzoselenazoles from the three-component reactions of 2-iodoanilines, selenium powder, arylacetic acids or benzyl chlorides is described. The use of copper salt as catalyst and dimethyl sulfoxide (DMSO) as solvent are crucial to afford the title compounds in moderate to good yields (45–88%) with good functional group tolerance on the aromatic and heteroaromatic substrates.

α-Keto Acids as Acylating Agents in the Synthesis of 2-Substituted Benzothiazoles and Benzoselenazoles

Herein, we report the first decarboxylative oxidation of α-keto acids that is promoted by sodium metabisulfite (Na2S2O5) to obtain 2-substituted benzothiazoles and benzoselenazoles. Diaryl disulfides and diselenides were used as chalcogen sources, and the desired products were obtained in moderate to excellent yields. This protocol does not require an inert gas, transition metals, or harsh reaction conditions, and CO2 is released as an environmentally benign coproduct. The presence of Na2S2O5 was essential to guarantee that the reaction reached completion and afforded maximum product yields.

Supramolecular Wiring of Benzo-1,3-chalcogenazoles through Programmed Chalcogen Bonding Interactions

The high-yielding synthesis of 2-substituted benzo-1,3-tellurazoles and benzo-1,3-selenazoles through a dehydrative cyclization reaction has been reported, giving access to a large variety of benzo-1,3-chalcogenazoles. Exceptionally, these aromatic heterocycles proved to be very stable and thus very handy to form controlled solid-state organizations in which wire-like polymeric structures are formed through secondary N?Y bonding interactions (SBIs) engaging the chalcogen (Y=Se or Te) and nitrogen atoms. In particular, it has been shown that the recognition properties of the chalcogen centre at the solid state could be programmed by selectively barring one of its σ-holes through a combination of electronic and steric effects exerted by the substituent at the 2-position. As predicted by the electrostatic potential surfaces calculated by quantum chemical modelling, the pyridyl groups revealed to be the stronger chalcogen bonding acceptors, and thus the best ligand candidate for programming the molecular organization at the solid state. In contrast, the thiophenyl group is an unsuitable substituent for establishing SBIs in this molecular system as it gives rise to chalcogen-chalcogen repulsion. The weaker chalcogen donor properties of the Se analogues trigger the formation of feeble N?Se contacts, which are manifested in similar solid-state polymers featuring longer nitrogen-chalcogen distances. Building benzo-1,3-chalcogenazoles: A versatile four-step synthesis of 2-substituted benzo-1,3-selenazoles and -tellurazoles starting from 2-bromoaniline is reported (see figure; R=alkyl, alkenyl, phenyl, furanyl, thiophenyl, pyridyl and ferrocenyl groups). The solid-state arrangement shows that, depending on the electronic and geometrical properties of the substituent at the 2-position, one can control the wiring organization through two- (X?Y) or three-atoms (X?Y?X) secondary bonding interactions.

Copper-catalyzed three-component one-pot synthesis of substituted 2-aryl-1,3-benzoselenazoles

A simple copper-catalyzed, one-pot synthesis of 2-aryl-1,3-benzoselenazole derivatives was developed using inexpensive, readily available 2-iodoanilines, selenium powder, and aromatic aldehydes as the starting materials. The mild reaction conditions and simple procedure without ligands and other additives make this methodology an alternative for preparing these potential selenium-containing compounds very conveniently.

Synthesis of 2-Substituted 1,3-Benzoselenazoles from Carboxylic Acids Promoted by Tributylphosphine

We report a general, practical, and simple metal-free method for the synthesis of 2-substituted 1,3-benzoselenazoles by the reaction of bis(2-aminophenyl)diselenide with a wide range of carboxylic acids, promoted by tributylphosphine. This efficient reaction furnishes 2-aryl-1,3-benzoselenazoles in good yields and tolerates a variety of substituents at the aryl moiety of carboxylic acids. For the first time, 2-alkyl-1,3-benzoselenazoles could be obtained from aliphatic carboxylic acids and thiazolidine-4-carboxylic acid in high chemical yields. The use of focused microwave irradiation considerably decreased the reaction time from 48 to 2 h. The experimental data provide insights into the mechanism of the reaction. A metal-free synthesis of 2-substituted 1,3-benzoselenazoles by the reaction of bis(2-aminophenyl)diselenide with carboxylic acids, promoted by tributylphosphine is reported. For the first time, 2-alkyl-1,3-benzoselenazoles could be obtained from aliphatic carboxylic acids and thiazolidine-4-carboxylic acid in high chemical yields. Microwave irradiation reduced the reaction time.

One-pot preparation of 2-(alkyl)arylbenzoselenazoles from the corresponding N-(acetyl)benzoyl-2-iodoanilines via a microwave-assisted methodology

We report here the first example of a one-pot synthesis of 2-(alkyl)arylbenzoselenazoles from N-(acetyl)benzoyl-2-iodoanilines. The reaction was carried out in the presence of Woollins' reagent under microwave irradiation and resulted in moderate to good yields.

Direct synthesis of 2-aryl-1,3-benzoselenazoles by reaction of bis(2-aminophenyl) diselenides with aryl aldehydes using sodium metabisulfite

We present here a general and easy method for the synthesis of several 2-aryl-1,3-benzoselenazoles from the reaction of bis(2-aminophenyl) diselenides with different aryl aldehydes, promoted by the non-toxic inorganic reducing agent sodium metabisulfite (Na2S2O5) in DMSO at 120 °C. This efficient method furnishes in high yields the corresponding 2-aryl substituted 1,3-benzoselenazoles and tolerates a range of substituents at the aryl ring of aldehydes. The use of focused microwave irradiation decreases drastically the reaction time from 48 to 2 h.