Journal
SYNTHESIS-STUTTGART
Volume 49, Issue 12, Pages 2753-2760Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0036-1589496
Keywords
azaindoles; domino reaction; isogranulatimides; iminium salts; chromenoimidazoles; microwave
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Funding
- Ministry of Education and Science of the Russian Federation
- Russian Foundation for Basic Research [16-53-540004-Viet_a]
- Vietnam Academy of Science and Technology
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The reactivity of N-cyanomethyl quaternary salts of 4-, 5- and 7-azaindoles towards salicylic aldehydes has been studied. The interaction of azaindolium salts with salicylic aldehydes proceeds as a base-promoted domino reaction, giving the corresponding chromenoimidazopyrrolopyridines. In the case of the 7-(cyanomethyl)-7-azaindolium salt, the reaction was found to be more sensitive, but the use of the 1-methyl-substituted salt allowed the synthesis of the desired compounds, incorporating the heterocyclic core of isogranulatimide C, a marine natural product.
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