76784-93-5

Upstream product

• 186581-53-3 diazomethane 
• 76784-92-4 2-carboxymethylterephthalic acid 
• 6018-41-3 methyl coumalate 
• 1712-36-3 penta-2,3-dienedioic acid dimethyl ester 
• 76784-90-2 methyl 4-cyano-2-methoxycarbonylmethylbenzoate 
• 76784-89-9 methyl 4-amino-2-methoxycarbonylmethylbenzoate 
• 408335-76-2 4-amino-2-(carboxymethyl)benzoic acid 
• 65399-05-5 5-amino-3H-isobenzofuran-1-one 

Downstream Products

• 76784-94-6 dimethyl 2-methoxycarbonylmethyl-1,4-cyclohexanedicarboxylate 

Relevant academic research and scientific papers

Syntheses of Highly Substituted Benzenes via Diels-Alder Reactions with 2H-Pyran-2-ones

The 2H-pyran-2-ones (α-pyrones) 1 react as dienes in Diels-Alder reactions with acetylene derivatives.The primarely formed cycloadducts immediately aromatize to benzenes by CO2 elimination.Thus, methyl acetylenedicarboxylate (2a) gives dimethyl phthalates 3, and methyl acetylenediphosphonate (2b) gives dimethyl 1,2-phenylenediphosphonates 8.The reactions of 1-(dimethylamino)-1-methoxyethene (9) with 1 regioselectively produce N,N-dimethylanilines 10 and isomeric homophthalate derivatives 12.Naphthoquinones 14 could be generated from 1,4-benzoquinone (13) and 1 in the presence of acetic anhydride and Pd/C.Hydroxy-2H-pyran-2-ones 4 react via their trimethylsilyl ether 6 analogously with 2a to give dimethyl (trimethylsiloxy)phthalates 7 which are easily converted to phenols 5 by acid-catalyzed hydrolysis.