55574-10-2

Usage

Uses

Used in Pharmaceutical Industry:
4-Hydroxy-2-methoxy-2H-1,4-benzoxazin-3(4H)-one is used as an intermediate in the synthesis of DIBOA for its health-promoting effects in rats. 4-hydroxy-2-methoxy-2H-1,4-benzoxazin-3(4H)-one plays a crucial role in the development of pharmaceuticals that can potentially benefit human health.
Used in Agricultural Industry:
As an intermediate in the synthesis of DIBOA, 4-hydroxy-2-methoxy-2H-1,4-benzoxazin-3(4H)-one contributes to the production of an allelopathic biochemical that is produced by grasses. This can be utilized in the agricultural industry to manage plant growth and competition, ultimately improving crop yield and quality.

Upstream product

• 55544-85-9 methyl α-(2-nitrophenoxy)-α-methoxyacetate 

Downstream Products

• 17359-54-5 2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one 
• 59-49-4 2-Benzoxazolinone 

Relevant academic research and scientific papers

Analogues of the Cyclic Hydroxamic Acid 2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3-one: Decomposition to Benzoxazolinones and Reaction with β-Mercaptoethanol

Analogues of the aglucones of naturally occurring cyclic hydroxamic acids (2,4-dihydroxy-1,4-benzoxazin-3-ones) from Gramineae (Poaceae) have been synthesized by the reductive cyclization of the ring-substituted methyl α-(o-nitrophenoxy)-α-methoxyacetates, followed by demethylation of the C-2 methoxy group with BBr3 or BCl3 to reveal the 2-hydroxy group.A structure-activity series was produced by varying the substituent at C-7 on the aromatic ring .The pKa values for the hydroxamic acid and the phenol moieties were determined for each member of the C-7 series.They correlated well with ? in a linear free energy relationship (LFER) yielding values of ρ = 0.71 (with ?p) for pKa1 (the hydroxamic acid) and ρ = 1.6 (with ρm) for pKa2 (the phenol).A LFER also existed between the rate constants for the unimolecular decomposition of these hydroxamic acids to benzoxazolinones and ?+ (ρ = -1.1).The rates of hydroxamic acid reduction to lactams by β-mercaptoethanol were also investigated.It was found that only compounds with electron-rich aromatic rings and specifically an oxa functionality para to the hydroxamic acid nitrogen atom (compounds 1 and 3 - 5) had measurable rates of reduction. 1H NMR spectra recorded during this reaction in D2O buffers (pD 9), however, showed that compounds 1, 2, 6 - 9 (the only ones investigated) formed a hemithioacetal at C-2 even though only 1 has a measurable rate of reduction by the same thiol.The remarkable rate enhancement provided by an oxa functionality suggests that reduction occurs by direct attack of thiolate on the hydroxamic nitrogen of a resonance-stabilized ion pair.