90901-58-9

Upstream product

• 3100-93-4 2,4-dimethylphenylisocyanide 
• 75-56-9 methyloxirane 

Downstream Products

• 954420-78-1 3,6-dimethyl-1,1-[3-(dimethylamino-(phenylethyl)-methyl)-pentamethylene]-1,3,4,9-tetrahydropyrano[3,4-b]indole 
• 954420-79-2 3,6-dimethyl-1,1-[3-(dimethylamino-(4-chlorophenyl)-methyl)-pentamethylene]-1,3,4,9-tetrahydropyrano[3,4-b]indole 
• 954420-75-8 3,6-dimethyl-1,1-[3-(dimethylamino-(3-fluorophenyl)-methyl)-pentamethylene]-1,3,4,9-tetrahydropyrano[3,4-b]indole 
• 954420-74-7 3,6-dimethyl-1,1-[3-(dimethylamino-(4-fluorophenyl)-methyl)-pentamethylene]-1,3,4,9-tetrahydropyrano[3,4-b]indole 
• 954420-77-0 3,6-dimethyl-1,1-[3-(dimethylamino-(phenyl)-methyl)-pentamethylene]-1,3,4,9-tetrahydropyrano[3,4-b]indole citrate 
• 863514-14-1 3,6-dimethyl-1,1-(3-dimethylamino-3-phenyl-pentamethylen)-1,3,4,9-tetrahydro-pyrano-[3,4-b]-indol 

Relevant academic research and scientific papers

INDOLE SYNTHESES UTILIZING o-METHYLPHENYL ISOCYANIDES.

New indole synthesis starting with o-methylphenyl isocyanides such as o-tolyl, 2,4-xylyl, and 2,6-xylyl isocyanide is described. Treatment of o-tolyl isocyanide with LDA in diglyme at minus 78 degree C generated selectively o-(lithiomethyl)phenyl isocyanide in an almost quantitative yield, which on warming up to room temperature was cyclized to indole after aqueous workup. Similarly, 2,4-xylyl and 2,6-xylyl and 2,6-xylyl isocyanides were cyclized to 5-methylindole and 7-methylindole quantitatively. The o-(lithiomethyl)phenyl isocyanides reacted with electrophiles such as alkyl halides and alkylene oxides to give o-alkylphenyl isocyanides, which were cyclized via the lithiation at the orthobenzylic carbon to afford 3-substituted indoles.