66628-73-7

Upstream product

• 95-55-6 2-amino-phenol 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 875219-68-4 dimethyl (2Z,4Z)-3,4-dioxo-1,6-hexanedioate 
• 51575-86-1 dimethyl 2,3-dibromobutane-1,4-dicarboxylate 

Downstream Products

• 1627615-47-7 methyl (Z)-2-(2-(4-benzylpiperazin-1-yl)-2H-benzo[b][1,4]oxazin-3(4H)-ylidene)acetate 
• 1627615-37-5 methyl (Z)-2-(2-(dibenzylamino)-2H-benzo[b][1,4]oxazin-3(4H)-ylidene)acetate 
• 1627615-13-7 4-(2-hydroxyphenylamino)-5-methoxyfuran-2(5H)-one 
• 82296-12-6 methyl 2-chloromethyl-5-ethoxycarbonyl-1-(2-hydroxyphenyl)imidazole-4-carboxylate 
• 82296-11-5 dimethyl 2-chloromethyl-1-(2-hydroxyphenyl)imidazole-4,5-dicarboxylate 
• 82296-10-4 ethyl 2-methoxycarbonyl-4H-imidazo<2,1-c><1,4>benzoxazine-1-carboxylate 
• 82296-27-3 dimethyl 1-(2-hydroxyphenyl)-2-methylimidazole-4,5-dicarboxylate 
• 82296-08-0 4H-imidazo<2,1-c><1,4>benzoxazine 

Relevant academic research and scientific papers

Synthesis and Biological Assessment of Pyrrolobenzoxazine Scaffold as a Potent Antioxidant

Reduction of mitochondrial oxidative stress-mediated diseases is an important pharmaceutical objective in recent biomedical research. In this context, a series of novel pyrrolobenzoxazines (PyBs) framework with enormous diversity (compounds 5a-w) was synt

Synthesis, Structure, and Biological Activity of Products of Reactions of 3,4-Dioxohexane-1,6-dioic Acid Esters with 2-Aminophenol

Bioactive derivatives of 1,4-benzoxazine have been prepared via reactions of 3,4-dioxohexane-1,6- dioic (ketipic) acid esters with 2-aminophenol. (2'Z)-2,2'-(2-Hydroxy-2H-1,4-benzoxazin-2-yl-3-ilidene)diacetic acid esters or (2Z)-[2-oxo-2H-1,4-benzoxazin-

Synthesis, in vitro antibacterial activity against Mycobacterium tuberculosis, and reverse docking-based target fishing of 1,4-benzoxazin-2-one derivatives

Seventeen 1,4-benzoxazin-2-ones bearing the enaminone moiety and three of their analogs were tested for the antibacterial activity against Mycobacterium tuberculosis (H37Rv). Minimal bactericidal concentrations (MBCs) were determined after 41 days of incu

Design, synthesis and antimycobacterial activity of benzoxazinone derivatives and open-ring analogues: Preliminary data and computational analysis

This study examines in depth benzoxazine nucleus for antimycobacterial property. We synthesized some benzoxazin-2-one and benzoxazin-3-one derivatives, which were tested for activity against a panel of Mycobacterium tuberculosis (Mtb) strains, including H37Ra, H37Rv and some resistant strains. Several compounds displayed a high antimycobacterial activity and the three isoniazid analogue derivatives 8a-c exhibited a MIC range of 0.125–0.250 μg/mL (0.37–0.75 μM) against strain H37Ra, therefore lower than the isoniazid reference drug. Two benzoxazin-2-one derivatives, 1c and 5j, together with isoniazid-analogue compound 8a, also revealed low MIC values against resistant strains and proved highly selective for mycobacterial cells, compared to mammalian Vero cells. To predict whether molecule 8a is able to interact with the active site of InhA, we docked it into the crystal structure; indeed, during the molecular dynamic simulation the compound never left the protein pocket. The more active compounds were predicted for ADME properties and all proved to be potentially orally active in humans.

Hydroamination reactions of alkynes with ortho-substituted anilines in ball mills: Synthesis of benzannulated N-heterocycles by a cascade reaction

It was demonstrated that ortho-substituted anilines are prone to undergo hydroamination reactions with diethyl acetylenedicarboxylate in a planetary ball mill. A sequential coupling of the intermolecular hydroamination reaction with intramolecular ring cl

Expedient synthesis of novel 1,4-benzoxazine and butenolide derivatives

A highly efficient and rapid method for the synthesis of 2-hydroxy-1,4-benzoxazine and butenolide derivatives has been developed. The key step in this protocol involves the reduction of benzoxazinone derivatives. Further reaction of 2-hydroxy-1,4-benzoxazine with secondary amines and sodium methoxide affords the corresponding 2-amino-1,4-benzoxazines and butenolide derivatives, respectively, in good yields.

Introduction of a clean and promising protocol for the synthesis of β-amino-acrylates and 1,4-benzoheterocycles: An emerging innovation

A highly efficient, elegant and simple procedure with exceptionally mild conditions has been proposed for the synthesis of β-amino-acrylate derivatives and an array of biologically and pharmaceutically active benzoheterocycles. The protocol offers a valua

Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: Novel antibacterial agents against Mycobacterium tuberculosis

Menaquinone is an essential component of the electron transport chain in many pathogens and consequently enzymes in the menaquinone biosynthesis pathway are potential drug targets for the development of novel antibacterial agents. In order to identify lea

Vinyltriphenylphosphonium salt mediated synthesis of 1,4-benzoxazine and coumarin derivatives

Protonation of the reactive 1:1 intermediate produced in the reaction between triphenylphosphine and dimethyl acetylenedicarboxylate by 2-aminophenol, 3-aminophenol, 4-aminophenol and 2-amino-3-hydroxypyridine leads to vinyltriphenylphosphonium salts, whi

Structural Elucidation of the Reaction Products of Benzoxazole Derivatives with Dimethyl Acetylenedicarboxylate. V

Benzoxazole and o-aminophenol each reacted with dimethyl acetylenedicarboxylate (DMAD) to give the same product, which was previously suggested to be a benzoxazinepyran derivative (2).An X-ray crystallographic analysis has now shown the structure of this compound to be trimethyl 2,3-dihydro-2-oxo-4H-1,4-benzoxazine-Δ3,7-aconitate.A similar treatment of o-aminophenols and β-aminoalcohols with an excess of DMAD afforded new 1,4-benzoxazines and 1,4-oxazines, respectively.Keywords benzoxazole derivative; dimethyl acetylenedicarboxylate; X-ray analysis; o-aminophenol; β-aminoalcohol; 1,4-benzoxazine; 1,4-oxazine