Abstract
It is found that 2-chloroquinoxaline 1-N-oxide readily undergoes nucleophilic substitution with ammonia, alkalies, and 4-acetyl-aminobenzenesulfonamide, giving the 1-N-oxides of 2-amino,2-hydroxy, and 2-(4′-acetylaminobenzenesulfonamido) derivatives of quinoxaline. Treatment of 2-chloroquinoxaline 1-N-oxide with thiourea or hydrazine leads not only to nucleophilic substitution, but also to oxidation-reduction processes, with formation of respectively 2-thio- and 2-aminoquinoxaline. With 2-bromomethylquinoxaline 1,2-di-N-oxide, replacement of the bromine by a thiuronium group is not accompanied by deoxidation of the nitrogen atoms.
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References
A. H. Gowenlock, G. T. Newbold, and F. S. Spring, J. Chem. Soc., 622, 1945.
E. Shaw, J. Bernstein, K. Losee, and W. A. Lot, J. Am. Chem. Soc., 72, 4362, 1950.
United States Patent 2749350, 1956; C. A., 51, 494, 1957.
A. S. Elina and L. G. Tsyrul'nikova, ZhOKh, 33, 1544, 1963.
A. S. Elina, ZhOKh, 32, 2967, 1962.
F. J. Wolf, R. M. Wilson, Jr, and M. Tishler, J. Am. Chem., 76, 2266, 1954.
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Elina, A.S. Quinoxaline N-oxides. Chem Heterocycl Compd 3, 740–741 (1967). https://doi.org/10.1007/BF00468364
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DOI: https://doi.org/10.1007/BF00468364