PURPOSE: To provide a new indole derivative which is useful as a synthetic intermediate for 5-aziridino-3-hydroxymethyl-1-methyl-2-(1H-indole-4,7-dione) prop-β-en-α-ol having antitumor activity.
CONSTITUTION: The indole derivative of formula I (R1 is lower alkoxymethyl, formyl; R2 is lower alcohol; R3 is H, lower alcohol; R4 is H, lower alkyl), for example, 5-hydroxy-3-methoxycarbonyl-2-methoxymethyl-1-methylindole. The reaction of 1,4-benzoquione of formula II with a compound of formula III (R1a is lower alkyl) gives a compound of formula Ia where R1 is lower alkoxymethyl. Then, a lower alkyl halide is allowed to react on the compound of formula Ia to give a compound of formula Ib (R3a is lower alkyl) where both R3 and R4 are lower alkyl. Then, the compound of formula Ib is reacted with an oxidizer to give a compound of formula Ic where R1 is formyl.
ARAI HITOSHI
NISHIKAWA HIROSHI
OGASA TAKEHIRO
KINUGAWA MASAHIKO
TOMIOKA SHINJI
