346669-61-2

Upstream product

• 346669-60-1 5-[1-hydroxy-2-[4-(methoxycarbonyl)-1-(methoxymethyl)-1H-pyrrol-2-yl]-2-[(4-methylphenyl)sulfonyl]ethyl]-1-methyl-1H-pyrrole-3-carboxylic acid methyl ester 
• 155345-18-9 methyl 1-methoxymethyl-5-tosylmethyl-1H-pyrrole-3-carboxylate 
• 155345-20-3 methyl 2-hydroxymethyl-N-methoxymethylpyrrole-4-carboxylate 
• 155345-19-0 methyl 2-formyl-N-methoxymethylpyrrole-4-carboxylate 
• 119580-82-4 methyl 2-formyl-N-methyl-4-pyrrolecarboxylate 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 5910-05-4 methyl 2-formyl-4-pyrrolcarboxylate 

Downstream Products

• 346669-56-5 methyl 2-[2-acetoxy-2-(4-methoxycarbonyl-N-methylpyrrol-2-yl)-1-tosyl]ethenyl-N-methoxymethylpyrrol-4-carboxylate 
• 170431-00-2 dimethyl 3-acetyl-5-acetoxy-6-methyl-4-tosyl-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-1,8-dicarboxylate 
• 346669-57-6 dimethyl 5-acetoxy-3-methoxymethyl-6-methyl-4-tosyl-3,6-dihydropyrrolo[3,2-e]indole-1,8-dicarboxylate 
• 346669-58-7 dimethyl 4-acetoxy-3-methyl-5-tosyl-3,6-dihydropyrrolo[3,2-e]indole-1,8-dicarboxylate 
• 346669-59-8 dimethyl 4-hydroxy-3-methyl-5-tosyl-3,6-dihydropyrrolo[3,2-e]indole-1,8-dicarboxylate 

Relevant academic research and scientific papers

Preparation of phenanthrenes by photocyclization of stilbenes containing a tosyl group on the central double bond. A versatile approach to the synthesis of phenanthrenes and phenanthrenoids

We have developed a useful modification of the classical preparation of phenanthrenes by UV irradiation of stilbenes in the presence of an oxidant. This modification involves the irradiation, in the presence of base, of stilbenes possessing a sulfonyl group linked to the central double bond. We have proved that this protocol can be successfully applied for the synthesis of diverse phenanthrenes and phenanthrenoids.

Base-Induced Photocyclization of 1,2-Diaryl-1-tosylethenes. A Mechanistically Novel Approach to Phenanthrenes and Phenanthrenoids

(Equation presented) The irradiation with UV light of a number of 1,2-diaryl-1-tosylstilbenes, in the presence of base, leads to the corresponding phenanthrenes and heterocyclic analogues. These results are consistent with a mechanism involving the base-induced elimination of p-toluenesulfinic acid from an intermediate 9-tosyl-4a,4b-dihydrophenanthrene, formed by photochemical cyclization of the starting 1,2-diaryl-1-tosylstilbenes.