- Electrochemical Rearrangement of 3-Hydroxyoxindoles into Benzoxazinones
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We report an unexpected rearrangement of 3-hydroxyoxindoles into benzoxazinones using electrochemistry. Our reaction employs mild and environmentally friendly conditions, and the benzoxazinone products are obtained in moderate to excellent yields. Mechanistic experiments suggest that a peroxide intermediate is likely involved.
- Vayer, Marie,Pastor, Miryam,Kofink, Christiane,Maulide, Nuno
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- Trifluoroacetic acid catalyzed dibenzodiazocine synthesis: Optimization and mechanism study
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Dibenzo[b,f][1,5]diazocines, a class of potential building blocks for novel electrochemical actuators, were synthesized via a novel, efficient acid-catalyzed reaction of 2-acylbenzoisocyanate at room temperature. Real-time NMR analysis and the captured intermediate showed the mechanism was an unprecedented cyclization of the isocyanate with the neighboring acyl group, followed by the dimerization.
- Zhao, Na,Qiu, Li,Wang, Xiao,Li, Jianzhong,Jiang, Yi,Wan, Xiaobo
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p. 9665 - 9671,7
(2020/08/20)
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- Friedel-Crafts Acylation with 2-Isocyanatobenzoyl Chlorides: The Structure of the Intermediate Complex
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The intermediate complex obtained in the Friedel-Crafts acylation of benzene with 2-isocyanatobenzoyl chloride (1a) reacts with methanol or ethanol in the presence of ether affording 4-alkoxy-4-phenyl-1,4-dihydro-3,1-benzoxazin-2(1H)-ones, whereas with anilines, the corresponding anils of 2-aminobenzophenone are obtained.In the presence of triethylamine, the complex reacts with aniline and 2-aminobenzophenone affording 4-hydroxy-4-phenyl-3-substituted 3,4-dihydroquinazolin-2(1H)-ones whereas, with alkyl anthranilates, the new 11b-phenyl-7,11b-dihydroquinazolinobenzoxazine-6,13-diones are obtained.Similar products are also obtained from 5-chloro-2-isocyanatobenzoyl chloride.The intermediate complex has been shown to exist exclusively in the cyclic form in both acidic and basic media.
- Acharya, Baman Prasad,Rao, Y. Ramachandra
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p. 1001 - 1035
(2007/10/02)
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