91148-63-9

Upstream product

• 67-56-1 methanol 
• 5100-23-2 2-isocyanatobenzoyl chloride 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 
• 71-43-2 benzene 
• 139018-14-7 3-hydroxy-3-phenyl-1,3-dihydro-indol-2-one 
• 100-58-3 phenylmagnesium bromide 
• 91-56-5 indole-2,3-dione 

Downstream Products

• 71526-50-6 6-Chloro-4,4-diphenyl-1,2-dihydro-3,1-benzoxazin-2(4H)-one 
• 111838-46-1 3-(2-benzoylphenyl)-4-hydroxy-4-phenyl-3,4-dihydroquinazolin-2(1H)-one 
• 111838-52-9 N-(2-benzoylphenyl)-N'-(2-methoxycarbonylphenyl)urea 
• 106537-08-0 (2-{[1-(2-Amino-phenyl)-1-phenyl-meth-(Z)-ylidene]-amino}-phenyl)-phenyl-methanone 
• 13143-05-0 N-(2-benzoylphenyl)-N'-phenylurea 
• 106537-13-7 2-chloro-6,12-diphenyl-dibenzo<1,5>diazocine 
• 91148-55-9 3-(2'-benzoylphenyl)-1,2,3,4-tetrahydroquinazoline-2,4-dione 
• 7139-42-6 6,12-diphenyl-dibenzo<1,5>diazocine 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 

Relevant academic research and scientific papers

Electrochemical Rearrangement of 3-Hydroxyoxindoles into Benzoxazinones

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.

Friedel-Crafts Acylation with 2-Isocyanatobenzoyl Chlorides: The Structure of the Intermediate Complex

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.

Friedel-Crafts Acylation of Some Aromatic Compounds with 2-Isocyanatobenzoyl Chloride

Friedel-Crafts acylation of benzene, toluene, anisole and chlorobenzene with 2-isocyanatobenzoyl chloride (1) afford either 2-aminobenzophenones (2) or 4,4-diaryl-1,2-dihydro-3,1-benzoxazin-2(4H)-ones (3) as major products depending on reaction temperature and/or substrate reactivity.Other minor products isolated are 3-aryl-1,2,3,4-tetrahydroquinazoline-2,4-diones (4), 6,12-diaryldibenzodiazocines (6) and 2-aminophenyl-α,α-diarylmethanols (7).The formation of 2 and 3 has been shown to take place via a common intermediate complex to which the cyclic 4-aryl-3,1-benzoxazinonium ion structure (12) has been assigned on the basis of its rection with methanol and 2-aminobenzophenone.While the formation of 6 occurs through the intermediate complex (12), 4-aryliminoquinazolin-2-ones (5) are formed most probably from the 1-AlCl3 complex.