- Ruthenium catalyzed chemo and site-selective C-H amidation of oxobenzoxazine derivatives with sulfonyl azides
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An efficient, novel and general protocol towards the synthesis of highly functionalized ortho-amido oxobenzoxazine frameworks via ruthenium catalyzed intermolecular C-H amidation using sulfonyl azides as amidation components has been successfully developed for the first time. The salient features of this strategy are high chemo and site-selectivity, a wide range of substrate scope with excellent yields and good functional group tolerance.
- Bakthadoss, Manickam,Kumar, Polu Vijay,Kumar, Ravan,Surendar, Manickam,Sharada, Duddu S.
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supporting information
p. 14190 - 14195
(2019/09/18)
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- Cp*RhIII-Catalyzed Directed Amidation of Aldehydes with Anthranils
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An approach towards construction of amide C–N bonds under mild conditions through rhodium(III) catalysis has been explored. Previous waste-free amidations were generally limited to the condensation of carboxylic acids and amines. In this report, we directly applied amination of the aldehyde C(sp2)–H bond to extend the scope of amidation reactions. The amination shows a wide substrates scope, and several important functional groups were tolerated under the benign reaction conditions. The synthesized amides are important precursors for the preparation of benzoxazinone derivatives, found in various bioactive natural products.q.
- Debbarma, Suvankar,Sudan Maji, Modhu
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p. 3699 - 3706
(2017/07/22)
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- Synthesis of 2-Aryl-4H-3,1-Benzoxazin-4-ones: A Class of α-Chymotrypsin Inhibitors
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Twenty one derivatives of 2-aryl-4H-3,1-benzoxazin-4-one were synthesized and their potential therapeutically significance and structureactivity relationship were tested against α-chymotrypsin. Majority of synthesized compounds showed significant in vitro α-chymotrypsin inhibitory properties having IC50values in the range of 5.42 ± 1.66 - 41.27 ± 1.33 μM, whereas standard inhibitor chymostatin have IC50 value 7.13 ± 1.06 μM. In the present series compounds 2-(2-fluorophenyl)-4H-3,1-benzoxazin-4-one (3h), 2-(2-bromophenyl)-4H-3,1- benzoxazin-4-one (3n) and 2-(1-naphthyl)-4H-3, 1-benzoxazin-4-one (3t) with IC50values 7.22 ± 0.75, 6.99 ± 0.29 and 5.42 ± 1.66 μM, respectively were found to be most active members of series, even better than standard inhibitor a-chymostatin.
- Khan, Zulfiqar Ali,Afzal, Noshaba,Hussain, Zaib,Naqvi, Syed Ali Raza,Bari, Ayesha,Shahzad, Sohail Anjum,Yar, Muhammad,Mahmood, Nasir,Bukhari, Shazia Anwer,Mansha, Asim,Zahoor, Ameer Fawad,Khan, Abdur Rahman,Ahmad, Matloob
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p. 4561 - 4565
(2014/12/10)
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- Synthesis and antimicrobial activity of 2-Aryl-4H-3,1-benzoxazin-4-ones
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Twenty derivatives of 2-aryl-4H-3,1-benzoxazin-4-one synthesized and their potential therapeutically significance tested against two strains of Gram positive bacteria (Staphylococcus aureus and Bacillus subtilis) and four strains of Gram negative bacteria (Shigella flexnari, Escherichia coli, Salmonella typhi and Pseudomonas aeruginsoa) by agar well diffusion method. The 2-(3-nitrophenyl)-4H-3,1-benzoxazin-4-one (3f) recorded significant antibacterial activity against Bacillus subtilis whereas 2-(4-bromophenyl)-4H-3, 1-benzoxazin-one (3o) exhibited weak antibacterial activity against Staphylococcus aureus. Further 2-(2-methylphenyl)-4H-3,1-benzoxazin-4-one (3b) showed significant activity against Shigella Flexnari, Escherichia coli, Pseudomonas aeruginsoa and Salmonella typhi. The antibacterial activity of synthesized derivatives of 2-aryl-4H-3,1-benzoxazin-4-one was compared to reference standard antibiotics amoxycillin, streptomycin, kanamycin and ciprofloxacin. The present study revealed that 2-aryl-4H-3,1-benzoxazin-4-ones possess good bactericidal activity against a panel of bacteria causing common bacterial diseases and therefore opens the possibility of finding latest clinically useful antibacterial compounds. The synthesized compounds were characterized by 1H NMR, EI, FT-IR and elemental analysis.
- Khan, Zulfiqar Ali,Naqvi, Syed Ali Raza,Shahzad, Sohail Anjum,Mahmood, Nasir,Yar, Muhammad,Zahoor, Ameer Fawad
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p. 152 - 156
(2013/02/22)
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- Facile synthesis and herbicidal evaluation of 2-Aryl-4H-3, 1-benzoxazin-4-ones
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The present work deals with the synthesis of 4H-3,1-benzoxazin-4-ones carrying an aryl functional group at position-2. Synthesized compounds tested for herbicidal activity at three different doses (500 μg/mL, 50 μg/mL and 5μg/mL). Most of the compounds exhibited significant herbicidal activity against Lemna aequinocitalis welv. at higher dose (500 μg/mL). Among the tested compounds 2-phenyl-4H-3,1-benzoxazin-4-one (3a) and 2-(3-chlorophenyl)- 4H-3,1-benzoxazin-4- one (3l) completely inhibited the plant growth at 500 and 50 μg/mL concentrations. All the synthetic compounds were characterized by FT-IR, 1H NMR, EI-MS and elemental analysis.
- Hussain, Zaib,Khan, Zulfiqar Ali,Naqvi, Syed Ali Raza,Shahzad, Sohail Anjum,Yar, Muhammad,Hussain, Abdullah Ijaz,Chatha, Shahzad Ali Shahid,Mahmood, Nasir,Khan, Khalid Mohammed
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p. 449 - 455
(2013/07/27)
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- 2,1-Benzisothiazoles. XIII . Intermediates and Products in the Sulfur Extrusion Reaction of 2,1-Benzisothiazolines-3(1H)-one. A New Synthesis of 11H-Pyridoquinazolin-11-one ("Pyracridone")
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Triethyl phosphite abstracts sulfur from 2,1-benzisothiazolin-3(1H)-one (1); a reaction intermediate is the spirocyclic compound 11, and products include the benzoxazine 6 and polyanthraniloyl compounds.In the presence of pyridine, pyracridone (13) is formed.The ketene-imine 9 is probably not an intermediate in these reactions.The reactions of other nucleophiles with 1 and with its N-methyl derivative 15, have been examined.
- Davis, Michael,Hook, Robert J.,Wu, Wen Yang
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p. 369 - 373
(2007/10/02)
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