252930-61-3

Usage

InChI:InChI=1/C12H9BrN2O/c13-10-3-1-2-4-11(10)15-12(16)9-5-7-14-8-6-9/h1-8H,(H,15,16)

Upstream product

• 14254-57-0 4-(chlorocarbonyl)pyridine 
• 615-36-1 2-bromoaniline 
• 55-22-1 pyridine-4-carboxylic acid 

Downstream Products

• 252930-63-5 N-(2-bromophenyl)-N-methyl-4-pyridinecarboxamide 
• 252930-65-7 N-methyl-N-phenyl-4-pyridinecarboxamide 
• 2295-47-8 2-(pyridin-4-yl)benzoxazole 
• 3034-31-9 N-phenylisonicotinamide 

Relevant academic research and scientific papers

Photocatalyst- And Transition-Metal-Free Visible-Light-Promoted Intramolecular C(sp2)-S Formation

A photocatalyst- and transition-metal-free visible-light-induced cyclization of ortho-halothiobenzanilides has been developed. Upon irradiation with visible light, substrates undergo dehalogenative cyclization to 2-aryl benzothiazoles with high efficiency and selectivity. This photocyclization exhibits a high tolerance to various functional groups, is applicable for the synthesis of 2-alkyl benzothiazoles, and is easy to set up for gram-scale reaction.

Synthesis of 2-pyridinylbenzoxazole: Mechanism for the intramolecular photosubstitution of the haloarene with the carbonyl oxygen of the amide bond in basic medium

2-Pyridinylbenzoxazole derivatives have been synthesized by the intramolecular photosubstitution reaction of N-(2- halophenyl)pyridinecarboxamide (1 and 2) with its amide bond in basic medium. In neutral medium both intramolecular photosubstitution and photoreduction reactions occurred. In the photosubstitution reaction a singlet state of the o-haloarene is involved, whereas in the photoreduction a triplet state of the o-haloarene is involved; oxygen inhibited the photoreduction but not the photosubstitution. The relative rate studies showed that a base accelerates the photosubstitution reaction but decelerates the photoreduction. o- Iodoarenecarboxamide is more reactive than o-bromoarenecarboxamide, which in turn is more reacitive than o-chloroarenecarboxamide. UV-vis absorption change in the presence of a base showed that an imidol and/or imidolate anion is involved in the reaction. Several transient species, such as charge- transfer excited states and a cyclohexadienyl anion radical, have been identified from the photolysis of 1 and 2 in basic medium by laser flash photolysis. In neutral medium dibromide anion radical and a phenyl radical were identified in addition to the above intermediates. On the basis of the photokinetic and laser flash photolysis studies, an intramolecular photosubstitution of N-(o-halophenyl)pyridinecarboxamide with its amide bond occurs via an intramolecular S(N)(ET)Ar* mechanism to afford 2- pyridinylbenzoxazole derivative, and the photoreduction proceeds via a free radical mechanism to give N-phenylpyridinecarboxamide.