In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Formation of 4(5)-aminoglyoxalines. I, published in 1930, which mentions a compound: 4531-54-8, mainly applied to , Recommanded Product: 4531-54-8.
The only evidence at present that 4(5)-aminoglyoxalines are true aromatic amines is the formation, after diazotization, of colored soln with aqueous β-C10H7ONa. Reduction of 4(5)-nitro-2-methyl- and 4(5)-nitroglyoxalines with Fe and H2O, FeSO4 and NaOH, Na2S or activated Al gave no basic material. Et glyoxaline-4(5)-carboxylate and N2H4.H2O, heated on the H2O bath for 30 min., give nearly quant. glyoxaline-4(5)-carboxyhydrazide, crystallizing with 1H2O, m. 213°, reduces NH4OH-AgNO3 slowly but not Fehling solution; picrate, yellow, m. 223° (decomposition), crystallizes from 85 parts boiling H2O. With HNO3 there results glyoxaline-4(5)-carboxyazide (I), decomposes explosively at 137°; heating with H2O does not give the urea; the green solution gives an amorphous picrate, chars 230°. Boiling I with absolute EtOH for 4 hrs. gives 42.2% of 4(5)-carbethoxyaminoglyoxaline, m. 180°; picrate, golden, decomposes 210°, crystallizes from 60 parts boiling H2O; nitrate (II), decomposes 143°. I and MeOH give 50% of the corresponding carbomethoxy derivative, m. 175°; picrate, decomposes 243°. Neither derivative could be hydrolyzed by acid or alkali. II and concentrated H2SO4 give 58% of 5(4)-nitro-4(5)-carbethoxyaminoglyoxaline, m. 234° (decomposition); this could not be converted by 10% Na2CO3 into the corresponding amine. 5-Chloro-4-nitro-1-methylglyoxaline and EtOH-NH3, heated 4 hrs. at 140°, give 63.7% of the 5-NH2 derivative, yellow, m. 303° (decomposition), crystallizes from 170 parts boiling H2O; it does not form an Ac derivative, a benzylidene derivative or a picrate; after treatment with HNO2, alk. C10H7ONa gives a greenish blue color and alk. m-C6H4(OH)2 a violet color. With 16% HCl, HNO2 is liberated and α-methylamino-α-hydroxyacetamide, pale brown, m. 140°, is formed.
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Reference:
Thiomorpholine – Wikipedia,
Thiomorpholine | C4H9NS – PubChem