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Sodium‐Ammonia Reductions in N‐Heteroaromatic Chemistry. Protodehalogenation and Protodealkylation of Sulphur Containing Pyrimidines, Pyridazines and S‐Triazines

par De Lannoy, J.;Gysen, A.;Hinkens, Raymonde
Référence Bulletin des Sociétés chimiques belges, 79, 5-6, page (329-336)
Publication Publié, 1970

Article révisé par les pairs

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Résumé :

The Birch reduction of chloro‐pyrimidine, ‐pyridazine and ‐s‐triazine derivatives bearing a prototropic substituent gives the corresponding dehalogenated compounds in good yields. Methylthio‐ and ethylthio‐substituents undergo a reductive cleavage: 4‐amino‐6‐methylthiopyrimidine (II) and 2,4‐bis‐diethylamino‐6‐ethylthio‐s‐triazine (III) are converted to the corresponding mercapto compounds. Moreover, the sodium‐ammonia reagent is able to remove a chlorine atom from a molecule containing a mercapto or alkylthio substituent; the efficiency of this reaction is shown by the one step reduction of 4‐amino‐6‐chloro‐2‐methylthiopyrimidine (VI) and 3‐chloro‐6‐mercaptopyridazine (VII) to the corresponding dehalogenated mercaptans in 66 and 58% yield, respectively. Copyright © 1970 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim