962-05-0

Upstream product

• 62-53-3 aniline 
• 2881-63-2 ethyl (4-chlorobenzoyl)acetate 
• 100-65-2 N-Phenylhydroxylamine 
• 173019-82-4 1-(3-bromo-prop-1-ynyl)-4-chloro-benzene 
• 99-91-2 para-chloroacetophenone 
• 19226-36-9 3-phenyl-5H-1,4,2-dioxazol-5-one 
• 495-18-1 Benzohydroxamic acid 
• 58303-62-1 5-(4-chlorophenyl)-2,3-dihydrofuran-2,3-dione 
• 98157-45-0 6-(4-chlorophenyl)-2,2-dimethyl-1,3-dioxin-4-one 

Downstream Products

• 93501-08-7 4-(4-chlorophenyl)-2-quinolinone 
• 103847-97-8 2,3-dihydro-5-p-chlorophenyl-7-phenyl-pyrrolo<3,4-e><1,4>-diazepine-6,8-(1H,7H)-dione 

Relevant academic research and scientific papers

1,4,2-Dioxazol-5-ones as Isocyanate Equivalents: An Efficient Synthesis of 2-Quinolinones via β-Keto Amides

Under thermal conditions, 1,4,2-dioxazol-5-ones are known to undergo decarboxylation followed by Lossen's rearrangement to yield isocyanates. Described herein is the in situ trapping of the resulting isocyanates with carbon nucleophiles to synthesize β-keto amides. Furthermore, a general and mild method for the conversion of the resulting β-keto amides into quinolin-2-ones is reported.

Copper-Catalyzed Aerobic Oxidations of 3-N-Hydoxyaminoprop-1-ynes to Form 3-Substituted 3-Amino-2-en-1-ones: Oxidative Mannich Reactions with a Skeletal Rearrangement

Cu-catalyzed aerobic oxidations of readily available 3-N-hydroxyaminopro-1-ynes with water, alcohols, or thiols to form diverse 3-substituted 3-amino-2-en-1-ones are described. The utility of this catalysis is manifested by a wide scope of applicable N-hydroxyl propargylamines and nucleophiles, thus enabling the design of one-pot cascade or two-step sequential reactions. Besides synthetic significances, such oxidative Mannich reactions are mechanistically interesting because structurally reorganized products were obtained. Our mechanistic studies reveal that the aerobic oxidations involve initial formation of nitrone intermediates, followed by the attack of nucleophiles. Herein, water and MeOH implement the conversion of nitrone intermediates to reaction products in two distinct pathways. Go Mannich! Cu-catalyzed aerobic oxidations of 3-N-hydroxyaminopro-1-ynes with water, alcohols, or thiols to form diverse 3-substituted 3-amino-2-en-1-ones are reported (see scheme). Such oxidative Mannich reactions are mechanistically interesting, because structurally reorganized products were obtained.

REACTION OF 2,2-DIMETHYL-6-ARYL-1,3-DIOXIN-4-ONES WITH AROMATIC AMINES AND o-PHENYLENEDIAMINE

N-Arylaroylacetamides and 4-aryl-1,5-benzodiazepin-4-ones were obtained by the thermolysis of 2,2-dimethyl-6-aryl-1,3-dioxin-4-ones in the presence of aromatic amines and o-phenylenediamine respectively.Investigetion of the reaction kinetics showed that the controlling stage is the generation of the aroylketenes, which takes place by a concerted -retrocycloaddition mechanism.