Regioselective formation of imidazol-2-yllithium, imidazol-4-yllithium, and imidazol-5-yllithium species was written by Groziak, Michael P.;Wei, Lulin. And the article was included in Journal of Organic Chemistry in 1991.Synthetic Route of C3H2I2N2 This article mentions the following:
Representative imidazol-2-yllithium, imidazol-4-yllithium, and imidazol-5-yllithium species have been prepared via halogen-metal exchange, and the propensity of the latter two to undergo isomerization and quench by electrophilic reagents has been studied. The C2-substituted imidazol-5-yllithium species (I) is generated within 10 min at -78° from 1-[(benzyloxy)methyl]-4,5-diiodoimidazole and affords the C5-formyl product II upon reaction with DMF, but gives the isomeric C2-formyl product III if allowed to equilibrate to the imidazol-2-yllithium species IV for an addnl. 35 min at -78° before quench. The less reactive electrophile di-Et carbonate is unable to trap I and instead reacts with IV to afford tris[1-[(benzyloxy)methyl]-4-iodo-2-imidazolyl]carbinol. In contrast, 1-[(benzyloxy)methyl]-4-iodoimidazole-5-carboxaldehyde ethylene acetal metalates to give the C2-unsubstituted imidazol-4-yllithium species, which undergoes a very rapid conversion to its imidazol-2-yllithium isomer, even at -100°, giving the 2,5-dicarboxaldehyde-5-ethylene acetal or the 2-deuterio 5-carboxaldehyde ethylene acetal V upon quench with DMF or D2O, resp. Thus, in the presence of C2 unsubstitution , C5 functionalization could be accomplished when the electrophile was sufficiently reactive, while C4 functionalization could not. Short- and long-range 1H-13C heteronuclear (Hetcor) 2D NMR spectroscopic analyses were instrumental in the structural assignments of key compounds In the experiment, the researchers used many compounds, for example, 4,5-Diiodo-1H-imidazole (cas: 15813-09-9Synthetic Route of C3H2I2N2).
4,5-Diiodo-1H-imidazole (cas: 15813-09-9) belongs to iodide derivatives. Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles. In the chemical industry, alkyl iodides serve as excellent alkylating agents and, specifically, methyl iodide is used as a methylating agent in the synthesis of various pharmaceutical drugs.Synthetic Route of C3H2I2N2
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com