1250698-75-9

Upstream product

• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 5961-59-1 N-methyl-N-(4-methoxyphenyl)amine 

Downstream Products

• 1374448-03-9 N-methyl-N-(4-methoxyphenyl)-2-diazo-3-oxobutanamide 
• 116707-99-4 1,3-dimethyl-5-methoxyindolin-2-one 
• 1537188-14-9 2-acetyl-3-hydroxy-N-(4-methoxyphenyl)-N-methylbut-2-enamide 
• 1537188-13-8 C₁₄H₁₇NO₄ 

Relevant academic research and scientific papers

Synthesis of 2-oxindoles via 'transition-metal-free' intramolecular dehydrogenative coupling (IDC) of sp2 C-H and sp3 C-H bonds

The synthesis of a variety of 2-oxindoles bearing an all-carbon quaternary center at the pseudo benzylic position has been achieved via a 'transition-metal-free' intramolecular dehydrogenative coupling (IDC). The construction of 2-oxindole moieties was carried out through formation of carbon-carbon bonds using KOt-Bu-catalyzed one pot C-alkylation of β-N-arylamido esters with alkyl halides followed by a dehydrogenative coupling. Experimental evidences indicated toward a radical-mediated path for this reaction.

Ruthenium-catalyzed intramolecular cyclization of diazo-β-ketoanilides for the synthesis of 3-alkylideneoxindoles

With [Ru(p-cymene)Cl2]2 as catalyst, diazo-β-ketoanilides would undergo intramolecular carbenoid arene C-H bond functionalization to afford 3-alkylideneoxindoles in up to 92% yields. The reaction occurs under mild conditions and exhibits excellent chemoselectivity. The lack of primary KIE (kH/kD ～ 1) suggests that the reaction should not proceed by rate-limiting C-H bond cleavage; a mechanism involving cyclopropanation of the arene is proposed.