Application of 2-(2-chloroaroyl)methyleneimidazolidines in domino and multicomponent reaction: new entries to imidazo[1,2-a]pyridines and benzo[b]imidazo[1,2,3-ij][1,8]naphthyridines

作者：Wen, Li-Rong; Jiang, Cui-Yu; Li, Ming^*; Wang, Li-Juan

来源：Tetrahedron, 2011, 67(2): 293-302.

DOI：10.1016/j.tet.2010.11.049

• 2-(2-Chloroaroyl)methyleneimidazolidines
• Heterocyclic ketene aminals (HKAs)
• Tetrahydroimidazo[1,2-a)pyridines
• Benzo[b]imidazo[1,2.3-ij][1,8]naphthyridines
• Multicomponent reaction

A new strategy for the synthesis of tetrahydroimidazo[1,2-a]pyridines and unusual tetrahydrobenzo[b]imidazo[1,2,3-ij][1,8]naphthyridines has been successfully developed by cascade reactions including Knoevenagel condensation, aza-ene reaction, imine-enamine tautomerization, cyclocondensation/oxidation, and intramolecular SNAr of precursors 2-(2-chloroaroyl)methyleneimidazolidines as new heterocyclic ketene aminals (HKA), which represent a class of polyfunctional scaffolds with four active reaction sites with aromatic aldehydes and malononitrile or ethyl 2-cyanoacetate under mild conditions. In this domino reaction, nine different active sites are involved, and two C-C bonds, two C-N bonds, and two new rings are constructed with all reactants efficiently utilized in the chemical transformation.

• 出版日期2011-1-14
• 单位青岛科技大学