Chromeno[2,3-c]pyrroles by one-pot multicomponent domino addition–amination reaction

A new aspect concerning chromone chemistry leading to the one-pot synthesis of chromeno[2,3-c]pyrroles is described. The synthesis involves a multicomponent reaction of 3-formylchromones with isocyanides and azodicarboxylates, whereupon novel chromeno[2,3-c]pyrrole derivatives were formed in good yi...

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Bibliographic Details
Published in:Tetrahedron letters 2014-10, Vol.55 (41), p.5601-5604
Main Authors: Terzidis, Michael A., Tsiaras, Vassilios G., Drosos, Nicolaos M., Kasapidou, Paraskevi M., Stephanidou-Stephanatou, Julia, Tsoleridis, Constantinos A., Buth, Gernot, Kostakis, George E.
Format: Article
Language:English
Subjects:
Azodicarboxylates
Chromeno[2,3-c]pyrroles
Formylchromones
Isocyanides
Multicomponent reactions
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Summary:A new aspect concerning chromone chemistry leading to the one-pot synthesis of chromeno[2,3-c]pyrroles is described. The synthesis involves a multicomponent reaction of 3-formylchromones with isocyanides and azodicarboxylates, whereupon novel chromeno[2,3-c]pyrrole derivatives were formed in good yields. The structures of the products were elucidated by 1D and 2D NMR experiments and were unambiguously confirmed by the use of crystal X-ray diffraction analysis. Full assignment of all 1H and 13C NMR chemical shifts has been achieved. A plausible mechanistic scheme is proposed.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.08.048