88521-67-9

Upstream product

• 104862-25-1 3-hydroxy-3-methyl-5-nitro-2,3-dihydrobenzofuran-2-carboxylic acid 
• 88521-72-6 ethyl 2-acetyl-4-nitrophenoxyacetate 
• 1450-76-6 1-(2-hydroxy-5-nitrophenyl)ethanone 
• 104862-17-1 ethyl 3-hydroxy-3-methyl-5-nitro-2,3-dihydrobenzofuran-2-carboxylate 
• 88521-63-5 2-acetyl-4-nitrophenoxyacetic acid 

Relevant academic research and scientific papers

ANTI-HIV COMPOUNDS

Thiazole derivatives represented by Formula (I) are disclosed, where R1, R2, R3, A, X, Y, Z, R6 and R7 are disclosed herein. These thiazole derivatives and pharmaceutical compositions comprising these derivatives are useful in the treatment of HIV mediated diseases and conditions.

Benzofuran Derivatives. Part 4. Synthesis of Benzofurans and 2,3,4,5-Tetrahydro-1-benzoxepin-3,5-diones

By treatment of ethyl 4- or 5-substituted 2-acetylphenoxyacetates 1 with potassium hydroxide in dry dioxane, benzofurans 2-7 and 2,3,4,5-tetrahydro-1-benzoxepin-3,5-diones 8 were obtained.The relative yields of benzofurans 2-7 and 2,3,4,5-tetrahydro-1-benzoxepin-3,5-diones 8 varied with the types of 4- or 5-substituents.The electron-donating 4-methoxyl group favored the formation of benzoxepins.On the other hand, electron-withdrawing substituents such as the 4-nitro group favored the formation of benzofurans.When esters 1 were treated with sodium amide,2,3-dihydrobenzofurans 2 were obtained exclusively regardless of 4- or 5-substituents.

Benzofuran Derivatives. Part 3 . On the Reactibities of the Intermediates in Benzofuran Synthesis

3-Methyl-5-nitrobenzofuran (2) and 3-methyl-5-nitrobenzofuran-2-carboxylic acid (3) were obtained by heating 2-acetyl-4-nitrophenoxyacetic acid (1) with various bases in acetic anhydride.It appeared that 3-hydroxy-3-methyl-5-nitro-2,3-dihydrobenzofuran-2-carboxylic acid (4) was the intermediate in the benzofuran synthesis.The properties of 4 were examined under various conditions.Using strong bases such as triethylamine in place of sodium acetate, 3-methyl-5-nitrobenzofuran-2-carboxylic acid (3) was obtained exclusively.However, in the presence of acetic acid in the reaction mixture 3-methyl-5-nitrobenzofuran (2) was obtained in good yield.The reaction pathways for the formation of 2 and 3 are discussed.

BENZOFURAN DERIVATIVES. I. ON THE EFFECTS OF SUBSTITUENTS IN BENZOFURAN SYNTHESES.

The Roessing's reaction of 4-substituted 2-acylphenoxyacetic acids give a mixture of benzofurans and 2-benzofurancarboxylic acids. The relative yields of benzofurans and 2-benzofurancarboxylic acids depend on the substituents on the benzene ring of the 2-acylphenoxyacetic acids. Electron-withdrawing substituents such as nitro groups favor the formation of 2-benzofurancarboxylic acids. On the other hand, the formation of benzofurans is favored by the steric hindrance of 2-acyl groups in the reaction of 2-acyl-4-nitrophenoxyacetic acids with anhydrous sodium acetate and acetic anhydride.