The Journal of Organic Chemistry

Formaldehyde: a reagent for the simultaneous protection of nucleophilic centers and the activation and stabilization of alternative locations to electrophilic attack. I. A …

AR Katritzky, K Akutagawa

Index: Katritzky, Alan R.; Akutagawa, Kunihiko Journal of Organic Chemistry, 1989 , vol. 54, # 12 p. 2949 - 2952

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Abstract

N-Unsubstituted benzimidazoles 1 are readily converted in a one-pot sequence into 2- substituted derivatives 2 with good overall yields. N-Protection with formaldehyde and lithiation with lithium Nfl-diisopropylamide (LDA), n-butyllithium, or tert-butyllithium gives the dilithiohemiaminals 6, which readily react with a range of electrophiles at the 2-carbon. The 2-substituted 1-(1ithioxymethyl) benzimidazoles 7 undergo smooth acidcatalyzed ...