64460-57-7

Upstream product

• 56-93-9 benzyltrimethylammonium chloride 
• 98-88-4 benzoyl chloride 
• 107-06-2 1,2-dichloro-ethane 
• 75-44-5 phosgene 
• 2148-56-3 2-chloro-6-aminobenzoic acid 
• 95-50-1 1,2-dichloro-benzene 
• 49684-74-4 C₁₂H₉ClN₂O 
• 19226-36-9 3-phenyl-5H-1,4,2-dioxazol-5-one 
• 495-18-1 Benzohydroxamic acid 
• 19407-43-3 2-benzoylamino-6-chloro-benzoic acid 

Relevant academic research and scientific papers

Rh(III)-Catalyzed C-H Diamidation and Diamidation/Intramolecular Cyclization of N-Iminopyridinium Ylides with Dioxazolones

A highly efficient Rh(III)-catalyzed C-H diamidation and diamidation/intramolecular cyclization of N-iminopyridinium ylides with dioxazolones has been developed, providing diamidated products and benzoxazinone products in good to excellent yields. Notably, the tunable selectivity of this reaction can be controlled by simply switching the solvent and the temperature. This reaction features operational simplicity, a broad substrate scope, and a good functional group tolerance.

Direct synthesis of benzoxazinones via Cp*Co(III)-catalyzed C–H activation and annulation of sulfoxonium ylides with dioxazolones

A highly novel and direct synthesis of benzoxazinones was developed via Cp*Co(III)-catalyzed C–H activation and [3 + 3] annulation between sulfoxonium ylides and dioxazolones. The reaction is conducted under base-free conditions and tolerates various functional groups. Starting from diverse readily available sulfoxonium ylides and dioxazolones, a variety of benzoxazinones could be synthesized in one step in 32%-75% yields.

Changes in the activity and selectivity of herbicides by selective fluorine substitution, taking bentranil and classic analogues as examples

The introduction of fluorine atoms into 2-phenyl-4H-3,1-benzoxazin-4-one (bentranil) led to sweeping changes in its herbicidal properties in some cases, and 5-fluoro-2-phenyl-4H-3,1-benzoxazin-4-one ('fluorobentranil') was found to be the most active compound. It can be prepared from 2-amino-6-fluoro-benzoic acid or by direct halogen exchange of 5-chloro-2-phenyl-4H-3,1-benzoxazin-4-one. The latter reaction was investigated on a pilot scale, including a high-temperature (350°C) potassium fluoride halogen exchange without solvent. When sulfolane was used as a solvent, a side reaction at 220°C - partial decomposition to a diphenylether - could be prevented by addition of a small amount of a radical scavenger. Other intermediates with a pseudohalogen substitution were obtained by side-chain chlorination of suitable methylsulfanyl benzoic acid precursors and halogen exchange. 'Fluorobentranil' shows good broad-leaf activity and selectivity on rice, cereals and maize. In a second case study, the fluoro-substituted anthranilic acids mentioned above were also found to be appropriate for synthesizing herbicidal sulfonylurea (SU) compounds via Meerwein reaction of their aniline function. Methyl 2-[({[(4-chloro-6-methoxy-2- pyrimidinyl)-amino]carbonyl}amino)sulfonyl]-6-fluorobenzoate is an example of a SU that is compatible with maize, whereas the unsubstituted Classic analogue is not selective.

Preparation of substituted 2-phenyl-4H-3,1-benzoxazin-4-ones

2-Phenyl-4H-3,1-benzoxazin-4-ones of the general formula I STR1 where R1 and R2 are each hydrogen or halogen, R1 may furthermore be methyl or methoxy and R2 may furthermore be haloalkyl, haloalkoxy, haloalkylmercapto or haloalkylsulfonyl, each of 1 to 3 carbon atoms, are prepared by reacting an appropriate anthranilic acid with an appropriate benzoyl halide in the presence of a base (acylation) and effecting ring closure by removal of water (cyclization), the process being carried out in a suspending agent which is immiscible with aqueous alkali metal hydroxide solution and in the presence of a phase-transfer catalyst.