32781-12-7

Upstream product

• 143082-98-8 p-(ethoxyphenyl)-3-(2-oxo-3,4-dihydro-2H-1,4-benzoxazin-(Z)-3-ylidene)benzoylpyruvamide 
• 139266-61-8 (2Z,4Z)-1,6-diphenyl-3,4-dihydroxy-2,4-hexadiene-1,6-dione 
• 95-55-6 2-amino-phenol 
• 143082-97-7 methyl 4-benzoyl-2,3-dioxo-1-(p-ethoxyphenyl)-2,3-dihydro-1H-pyrrole-5-carboxylate 
• 143108-61-6 methyl 3-benzoyl-4-hydroxy-2-(o-hydroxyphenylamino)-5-oxo-1-(p-ethoxyphenyl)-2,5-dihydropyrrole-2-carboxylate 
• 20577-73-5 methyl 4-phenyl-2,4-dioxobutanoate 
• 6296-54-4 ethyl 2,4-dioxo-4-phenylbutyrate 
• 1239902-47-6 3-[4-oxo-6-phenyl-3-cyclohexyl-2-(cyclohexylimino)-3,4-dihydro-2H-1,3-oxazin-5-yl]-2H-benzo[b][1,4]oxazin-2-one 
• 5817-92-5 2,4-dioxo-4-phenylbutanoic acid 
• 88330-79-4 2-hydroxy-4-oxo-4-phenylbut-2-enoic acid ethyl ester 
• 152449-24-6 methyl 4-oxo-4-phenyl-2-p-ethoxyphenylamino-2-butenoate 
• 142071-82-7 3-benzoylpyrrolo[2,1-c][1,4]benzoxazine-1,2,4-trione 
• 71971-24-9 2,4-dioxo-4-phenyl-butyric acid; monosodium salt 
• 98-86-2 acetophenone 

Downstream Products

• 142071-82-7 3-benzoylpyrrolo[2,1-c][1,4]benzoxazine-1,2,4-trione 

Relevant academic research and scientific papers

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.

Non-peptide-based new class of platelet aggregation inhibitors: Design, synthesis, bioevaluation, SAR, and in silico studies

A series of 2-oxo-2-phenylethylidene linked 2-oxo-benzo[1,4]oxazine analogues 17a–x and 18a–o, incorporated with a variety of electron-withdrawing as well as electron-donating groups at ring A and ring C, were synthesized under greener conditions in excel

“On water” ultrasound-assisted one pot efficient synthesis of functionalized 2-oxo-benzo[1,4]oxazines: First application to the synthesis of anticancer indole alkaloid, Cephalandole A

For the first time, an efficient, simple, synthetic green protocol for the one-pot synthesis of functionalized 2-oxo-benzo[1,4]oxazines 24–29 in water under ultrasound irradiation is presented. As compared to conventional methods, the present protocol avo

Microwave-assisted one-pot efficient synthesis of functionalized 2-oxo-2-phenylethylidenes-linked 2-oxobenzo[1, 4]oxazines and 2-oxoquino[1, 4]oxalines: Synthetic applications, antioxidant activity, SAR and cytotoxic studies

A microwave-assisted, environmentally benign green protocol for the synthesis of functionalized (Z)-3-(2-oxo-2-phenylethylidene)-3, 4-dihydro-2H-benzo[b][1, 4]oxazin-2-ones (11a-n) in excellent yields (upto 97%) and (Z)-3-(2-oxo-2-phenylethylidene)-3, 4-dihydroquinoxalin-2(1H)-ones (14a-h) (upto 96% yield) are reported. The practical applicability of developed methodology were also confirmed by the gram scale synthesis of 11a, 14c and 14e; synthesis of anticancer alkaloid Cephalandole A 16 (89% yield). All the synthesized compounds 11a-n, 14a-h and 16 were assessed for their in vitro antioxidant activities in DPPH radical scavenging and FRAP assay. In DPPH assay, compounds 11a, 14c and 14e, the most active compounds of the series, were found to show IC50 value of 10.20 ± 0.08 μg/mL, 9.89 ± 0.15 μg/mL and 8.97 ± 0.13 μg/mL, respectively in comparison with standard reference (ascorbic acid, IC50 = 4.57 μg/mL). Whereas, in FRAP antioxidant assay seven compounds (11c, 11e, 11i, 11k, 11l, 14d and 14h) displayed higher antioxidant activity in comparison to the reference standard BHT (C0.5FRAP = 546.2 μM). Moreover, the cytotoxic studies of the compounds 11a, 14c, 14e and 14h were found to be non-toxic in nature in 3T3 fibroblast cell lines using MTT assay.

Five-membered 2,3-dioxo heterocycles: XCVIII.* [4 + 2]-cycloaddition of alkyl vinyl ethers to 3-aroyl-1H-pyrrolo[2,1-c][1,4]benzoxazine-1,2,4- triones. A new synthetic approach to heteroanalogs of 13(14→8)-abeo steroids

3-Aroyl-1H-pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones reacted with alkyl vinyl ethers according to the [4 + 2]-cycloaddition pattern with formation of substituted (1S*,16R*)- and (1R*,16R*)-16-alkoxy-14- aryl-3,15-dioxa-10-azatetracyclo[8.7.0.01,13.04,9

Five-membered 2,3-dioxo heterocycles: LXXXVIII.* Reaction of 3-aroylpyrrolo[1,2-d][1,4]benzoxazine- 1,2,4(4H)-triones with N,N'-dicyclohexylcarbodiimide under thermolysis conditions

Thermolysis of 3-aroylpyrrolo[1,2-d][1,4]benzoxazine-1,2,4(4H)-triones generates aroyl(2-oxo-1,4- benzoxazin-3-yl)ketenes which react as dienes at the aroylketene fragment in [4 + 2]-cycloaddition at the C=N bond of N,N'-dicyclohexylcarbodiimide with form

Sulfamic acid as an effective catalyst in solvent-free synthesis of β-enaminoketone derivatives and X-ray crystallography of their representatives

Two types of β-enaminoketone derivatives of 3-(2-oxo-2-arylethylidene) -3,4-dihydro-1H-quinoxalin-2-ones and 3-(2-oxo-2-arylethylidene)-3,4-dihydro- benzo[1,4]oxazin-2- ones were effectively and conveniently prepared in good to excellent yields under solv

Chemistry of 2-methylene-2,3-dihydro-3-furanones 16.* The reaction of 2-acylmethylene-5-aryl-2,3-dihydro-3-furanones with aromatic amines and N-arylideneamines

2-p-Chlorobenzoylmethylene-5-phenyl-2,3-dihydro-3-furanone reacts with arylamines or N-arylideneamines to form the products of ring opening, 1,6-diaryl-1-arylamino-4-hydroxy-1,4-hexadiene-3,6-diones. The reaction of 5-aryl-2-p-chlorobenzoylmethylene-2,3-dihydro-3-furanones with o-aminophenol afforded 3-p-chlorobenzoylmethylene-3,4-dihydro-2H-benzo[b]-1,4-oxazin-2-one. Nucleophilic attack of amines is directed either to electrophilic centers at the C(5) and C(2) atoms or to the carbonyl group of the 2-phenacylidene substituent of the 3-oxofuran ring.

FIVE-MEMBERED 2,3-DIOXOHETEROCYCLES. XXXVII. REACTION OF 3-AROYL-1,2-DIHYDRO-4H-PYRROLOBENZOXAZINE-1,2,4-TRIONES WITH ALKYL- AND ARYLAMINES

3-Aroyl-1,2-dihydro-4H-pyrrolobenzoxazine-1,2,4-triones react with an equivalent amount of alkyl- and arylamines with the formation of N-substituted 3a-amino-3-aroyl-2-hydroxy-1,3a-dihydro-4H-pyrrolobenzoxazine-1,4-diones and N-substituted 4-aryl-2,4-dioxo-(Z)-3-(2-oxo-3,4-dihydro-2H-1,4-benzoxazin-3-ylidene)butyramides, which in the case of alkylamines exist as the ring isomers (Z)-3-(1-alkyl-5-aryl-5-hydroxy-2,3-dioxotetrahydro-4-pyrrolylidene)-3,4-dihydro-2H-1,4-benzoxazin-2-ones.An excess of the amine leads to the formation of (Z)-3-phenacylidene-3,4-dihydro-2H-1,4-benzoxazin-2-ones and substituted oxamides.

FIVE-MEMBERED 2,3-DIOXOHETEROCYCLES XXXI. REACTION OF 1-ARYL-4-AROYL-5-METHOXYCARBONYL-2,3-DIHYDRO-2,3-PYRROLEDIONES WITH o-AMINOPHENOL AND N-PHENYL-o-PHENYLENEDIAMINE

1-Aryl-4-aroyl-5-methoxycarbonyl-2,3-dihydro-2,3-pyrrolediones react with o-aminophenol and N-phenyl-o-phenylenediamine with the formation of 1-aryl-4-aroyl-5-methoxycarbonyl-3-hydroxy-5-o-hydroxyphenylamino- and 5-o-phenylaminophenylamino-2,5-dihydro-2-p