82679-09-2

Upstream product

• 525-76-8 2-methyl-4-oxo-3,1-benzoxazine 
• 67-63-0 isopropyl alcohol 
• 118-92-3 anthranilic acid 

Relevant academic research and scientific papers

Reactivity of 2-methyl-4H-3,1-benzoxazin-4-ones and 2-methyl-4H-pyrido[2,3- d][1,3]oxazin-4-one under microwave irradiation conditions

The reactivity of variably substituted 2-methyl-4H-3,1-benzoxazin-4-ones and 2-methyl-4H-pyrido[2,3-d][1,3]oxazin-4-one towards carbon and oxygen nucleophiles under microwave irradiation conditions was investigated. Optimization of the reaction conditions of oxazinones with carbon nucleophiles led to the synthesis of a series of 4-hydroxy-quinolin-2-ones and 4-hydroxy-1,8-naphthyridin-2-ones in high yields, whereas reaction with a variety of alcohols proceeded smoothly to the formation of the corresponding N-acetyl-anthranilates and nicotinates.

Acylanthranils. 11. Reaction of Acylanthranils with Alcohols To Give the Corresponding Esters

Although the reactions of acetylanthranil (1, R = CH3) with nucleophilic molecules of the type HNu usually occur "abnormally" via nucleophilic attack at the less electropositive center, C-2 (pathway A, Scheme II), it was shown that reactions of 1 with the anion form, Nu(1-), always occur "normally" via nucleophilic attack at the more electropositive center, C-4 (pathway B, Scheme II).Thus, reaction of 1 with ROH in the presence of a small amount of RO(1-) gives the corresponding o-acetamidobenzoate ester 4 in very good yields, rather than the corresponding acetimidate 3.These results are consistent with the hypothesis that the "abnormal" selectivity is attributable to formation of a molecular complex, 1*(HNu)n, via hydrogen bonding with the heterocyclic nitrogen atom of 1, which favors subsequent nucleophilic attack at the adjacent electropositive center at C-2.Since Nu(1-) cannot be restrained by the tether of hydrogen bonding to the electron donating atoms of 1, reaction occurs "normally" via direct nucleophilic attack at C-4.