The synthesis of heterocycles via addition-elimination reactions of 4- and 5-aminoimidazoles was written by Al-Shaar, Adnan H. M.;Chambers, Robert K.;Gilmour, David W.;Lythgoe, David J.;McClenaghan, Ian;Ramsden, Christopher A.. And the article was included in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) in 1992.Safety of 1-Methyl-4-nitroimidazole This article mentions the following:
4-Aminoimidazoles, e.g. I (R = H, R1 = H, Me, CH2Ph; R2 = H, Me, Et, CHMe2), undergo addition elimination reactions with electrophilic reagents to give exclusively N-adducts, which are useful intermediates for further synthetic transformations to novel heterocyclic systems. Thus, di-Et ethoxymethylenemalonate (II) and 4-amino-1-benzylimidazole give the adduct I [R = HC:C(CO2Et)2, R1 = CH2Ph, R2 = H], and subsequent acid-catalyzed cyclization gives the imidazo[4,5-b]pyridine III and a heterocyclic mesomeric betaine, which undergoes 1,3-dipolar cycloaddition with di-Me acetylenedicarboxylate to give two products. When the 2-alkyl-4-aminoimidazoles I (R = R1 = H, R2 = Me, Et, CHMe2) are generated in situ in the presence of II, 5,5′-diimidazoles are significant products; a mechanism for this novel transformation is proposed. 4-Amino-3-cyanoimidazo[1,5-a]pyrimidines IV (R = H, Me) are formed by cyclization of the N-adduct of I (R = R1 = R2 = H) and CR3(OEt):C(CN)2 (R3 = H, Me). The use of X:NCN [V; X = CH(OEt), CMe(OEt), C(SMe)2] leads to novel 4-aminoimidazo[1,5-a]-1,3,5-triazine derivatives VI (R1 = H, Me, SMe; R2 = H, Me), whose chem. reactions with both electrophilic and nucleophilic reagents are reported. 5-Aminoimidazoles, e.g., VII (R = H, R1 = Me, CH2CH2OH; R2 = Me, CHMe2), undergo addition-elimination reactions with the electrophilic reagents, e.g. II and V, to give N-adducts and/or C-adducts, depending upon the structure of the reagent. These stable addition-elimination products are usually obtained in good yield and are useful intermediates for further synthesis. Reaction of the amines VII with II gives mainly N-adducts VII [R = HC:C(CO2Et)2], which can be cyclized using phosphoryl chloride to give the versatile 7-chloroimidazo[4,5-b]pyridines VIII. With ethoxymethylenemalononitrile, the amines VII give C-adducts, which undergo thermal cyclization to give 5-amino-6-cyanoimidazo[4,5-b]pyridines IX, which are further transformed into novel heterocyclic systems, including the tricyclic imidazo[4′,5′:5,6]pyrido[2,3-d]pyrimidines X (R = H, Ph) and XI (R = H, Bu, CH2Ph, CH2CH2OH). Cyclization of the adducts obtained using V provides new synthetic route to aminopurine derivatives, e.g. XII (R3 = H, NH2, SMe), and hypoxanthines. The preference of electrophilic reagents for N– or C-addition to VII is rationalized using Frontier MO theory. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Safety of 1-Methyl-4-nitroimidazole).
1-Methyl-4-nitroimidazole (cas: 3034-41-1) belongs to imidazole derivatives. Imidazole derivatives generally have good solubility in protic solvents. Simple imidazole derivatives, such as 1H-imidazole, 2-methyl-1H-imidazole, and 1,2-dimethylimidazole, have very high solubility in water. Imidazole derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Safety of 1-Methyl-4-nitroimidazole
Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem