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The synthesis and properties of certain N ‐methylated 5‐diazouracils
Author(s) -
Thurber T. Craig,
Townsend Leroy B.
Publication year - 1975
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570120420
Subject(s) - chemistry , dimethylamine , diazo , covalent bond , methanol , solvent , medicinal chemistry , amine gas treating , organic chemistry
The reduction of 1‐methyl‐, 3‐methyl‐ and 1,3‐dimethyl‐5‐nitrouracil (Ia‐c) to the corresponding 5‐aminouracils (IIa‐c) is described. Diazotization of 5‐amino‐1‐methyluracil (IIa) and 5‐amino‐1,3‐dimethyluracil (IIc) gave 5‐diazouracils which were characterized as thermally stable C6 covalent hydrates (III and XIII). Diazotization of 5‐amino‐3‐methyluracil (IIb) gave anhydro 5‐diazo‐3‐methyluracil (X) which underwent covalent methanolation and thermally reversible covalent hydration. Treatment of III and XIII with hot methanol resulted in solvent exchange of the C6 hydroxyl groups by a mechanism which may involve initial formation of diazoethers. Treatment of the methanolates (IV, XI and XIV) with dimethylamine resulted in coupling at the diazo group with a concomitant expulsion of the C6 methoxyl groups to give 5‐(3,3‐dimethyl‐1‐triazeno)uracils (XVa‐c).