Aminomethylation of Imidazoheterocycles with Morpholine

Abstract

A hitherto unreported aminomethylation occurs at C-3 of imidazopyridines with morpholine in the presence of (diacetoxyiodo)benzene at ambient temperature in short reaction times. This methodology is also applicable to indolizine, imidazo[2,1-b]thiazole, benzo[d]imidazo[2,1-b]thiazole, and indole. Interestingly, the aminomethylation involving morpholine as a source of methylene group is a new phenomenon. This protocol is of much potential for the synthesis of aminomethylated derivatives under mild reaction conditions.

Direct synthesis of benzylic amines by palladium-catalyzed carbonylative aminohomologation of aryl halides

“…In addition, the dehydrogenative aminomethylations of activated aromatic compounds with amines and MeOH have also been realized by the catalysis of metal (Ru, Mn, Fe) pincer complex. [21][22][23] Despite their great efficiency, there are still some drawbacks to these reactions, such as the need to pre-functionalize substrates and a narrow substrate scope. Thus, developing general aminomethylation of aryl halides with non-expensive and easily available starting materials is still desirable.…”

Photoinduced, Direct C(sp2)−H Bond Azo Coupling of Imidazoheteroarenes and Imidazoanilines with Aryl Diazonium Salts Catalyzed by Eosin Y

“…Their structure is present in many pharmaceuticals and also has applications in material sciences . Therefore, it is not surprising that the synthesis and functionalization of imidazoheteroarenes have received considerable attention in different areas of scientific research . Analogously, arylazo compounds are widely used in several areas, including the chemical industry, pharmaceuticals, chemosensors, electronics, and liquid crystals ( 1 a – d , Figure ) .…”

Highly Efficient and Eco‐Benign Synthesis of 3‐Imidazoheterocyclic‐Substituted Phthalides/Isoindolinones in Water under Catalyst‐ and Additive‐Free Conditions

“…Also, the imidazopyridine core is associated with many commercially available drugs including saripidem, zolimidine, necopidem, olprinone, and alpidem. Due to the importance of imidazoheterocycles, several important advances have been reported for direct functionalization at the C3 position of imidazoheterocycles, including arylation, amination, dicarbonylation, cyanation and chalcogenation . Very recently, direct C3 coumarinylchalcogenation, heteroarylation, alkylselenation, and sulfenylation of imidazoheterocycles have been published by our group .…”