Journal
TETRAHEDRON
Volume 67, Issue 2, Pages 293-302Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.11.049
Keywords
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
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Funding
- National Natural Science Foundation of China [20872074, 21072110]
- Natural Science Foundation of Shandong Province [Z2008B03, ZR2010BM007]
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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. (C) 2010 Elsevier Ltd. All rights reserved.
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