-1-Methoxyindole-3-carbaldehyde is proved to be a versatile electrophile and reacts regioselectively at the 2-position with various types of nucleophiles providing 2-substituted indole-3-carbaldehydes.Indole is one of the electron rich hetero-aromatics. This is the reason why electrophilic substitution reactions have been well studied 2 in the indole chemistry (shown in general formula in Scheme 1, A). On the other hand, nucleophilic substitution reaction 3 was not familiar until we developed 1-hydroxyindole chemistry. 4 We demonstrated that a hydroxy or a methoxy group at the 1-position of indole skeleton functions as a good leaving group when at least one electron withdrawing group 3b,4 (ester, halogen) 3c is present in the indole nucleus (Scheme 1, B). Since various types of 1-hydroxy-and 1-methoxyindoles are available, 4 they can now be utilized as substrates for nucleophilc substitution reactions.
The Chemistry of Indoles. Part 139. Nucleophilic Substitution Reaction of 1-Methoxyindole-3-carbaldehyde. -A variety of 2-substituted indole-3-carbaldehydes is readily prepared by reaction of 1-methoxyindole-3-carbaldehyde (I) with S-, O-, N-, and C-nucleophiles. -(YAMADA, F.; SHINMYO, D.; NAKAJOU, M.; SOMEI*, M.; Heterocycles 86 (2012) 1, 435-453, http://dx.doi.org/10.3987/com-12-s(n)41 ; Fac. Pharm. Sci., Kanazawa Univ., Kanazawa 920, Japan; Eng.) -R. Staver 18-097
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