Synthesis of heteroxanthine from a derivative of imidazole was written by Sarasin, J.;Wegmann, E.. And the article was included in Helvetica Chimica Acta in 1924.Application In Synthesis of 1-Methyl-4-nitroimidazole This article mentions the following:
S. and W. describe a new synthesis of 7-methylxanthine from an imidazole derivative, by closing the pyrimidine ring, an operation which has not been previously effected. 1-Methyl-4-nitro-5-chloroimidazole (I) is obtained in theoretical yield from 1-methyl-5-chloroimidazole (b. 200°) (II) by dissolving in dilute HNO3 to form the nitrate, treating the latter with cold concentrated H2SO4, heating the mixture on the water bath for 2 hrs., and pouring the product on ice; it m. 147-8°, and is insoluble in acids and dilute alkalies. The isomeric 1-methyl-5-nitro-4-chloroimidazole (III), obtained by the same method from 1-methyl-4-chloroimidazole; m. 77-8°. I and III are reduced at 0° by Sn and HCl to the corresponding methylchloroaminoimidazoles which were not obtained in the pure state. I heated for several hrs. on the H2O bath in EtOH with 2 mols. KCN and 0.1 mol. KI yields 85% 1-methyl-4-nitro-5-cyanoimidazole (IV), m. 141-2°, insoluble in acids and dilute alkalies. 1-Methyl-4-nitroimidazole-5-carboxamide (V), obtained in 90% yield when IV is heated for 2 hrs. on the H2O bath with 8 times its weight of concentrated H2SO4 and the product is poured on ice, m. 257-8° (decomposes), insoluble in acids and alkalies, saponified with great difficulty; a small amount of the acid (VI) is obtained by prolonged action of concentrated HCl. VI m. 160° with evolution of CO2 and formation of 1-methyl-4-nitroimidazole (VII), m. 133-40°, which is also obtained by heating V in a sealed tube at 120° with HCl. Reduction of VII by Sn and HCl at 0° and hydrolysis of the product by heating under pressure with HCl, gives NH4Cl and sarcosine-HCl, m. 168-9°; this reaction establishes the constitution of II and VII. V is reduced at 0° by Sn and HCl to the corresponding amine, 1-methyl-4-aminoimidazole-5-carboxamide (VIII), m. 184-5°, decomposed when heated with water or dilute alkalies with evolution of NH3; HCl salt, m. 214-5°. 7-Methylxanthine (heteroxanthine) obtained in 38% yield by heating 0.4 g. of VIII for 8 hrs. in a sealed tube at 160-70° with an equal weight of CO(OEt)2, m. 380° (browning and evolution of gas). A mixture of the substance with heteroxanthine prepared from theobromine melts at the same temperature The murexide reaction is given with KClO3 and HCl. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Application In Synthesis of 1-Methyl-4-nitroimidazole).
1-Methyl-4-nitroimidazole (cas: 3034-41-1) belongs to imidazole derivatives. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole has become an important synthon in the development of new drugs. Imidazole is incorporated into many important biological compounds. The most pervasive is the amino acid histidine, which has an imidazole side-chain. Histidine is present in many proteins and enzymes, e.g. by binding metal cofactors, as seen in hemoglobin.Application In Synthesis of 1-Methyl-4-nitroimidazole
Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem