Abstract
Nitrosation of anhydrotetracycline (5) affords 9-nitrosoanhydrotetracycline (6), which is converted by sodium dithionite into 9-aminoanhydrotetracycline (7). Alkaline coupling of anhydrotetracycline with diazotized sulfanilic acid gives an azo dye which is reduced by sodium dithionite to give 7-aminoanhydrotetracycline (9). Reductive methylation of amines 7 and 9 with formaldehyde and sodium cyanoborohydride yields 9-dimethylaminoanhydrotetracycline (8) and 7-dimethylaminoanhydrotetracycline (10), respectively.
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