69622-45-3

Upstream product

• 460-07-1 N-acetylaziridine 
• 63212-31-7 o-lithiomethylphenyl isocyanide 

Downstream Products

• 1433999-59-7 tert-butyl (1Z)-1-(2-isocyanophenyl)prop-1-en-2-yl carbonate 
• 1433999-64-4 tert-butyl (1Z)-1-(2-isothiocyanatophenyl)prop-1-en-2-yl carbonate 
• 91-55-4 2,3-dimethylindole 
• 90901-69-2 o-(1-acetylethyl)phenyl isocyanide 

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.