Synthesis of Highly Functionalized 4-Iodo-7-azaindazoles via Condensation/Diels-Alder/Retro-Diels-Alder Cyclization of Iodoalkynones and 2-Hydrazineylpyrimidines

A method for the preparation of highly functionalized 4-iodo-7-azaindazoles is reported. These valuable heterocycles are synthesized via condensation of 2-hydrazineylpyrimidines with various iodoalkynones followed by Diels-Alder/retro-Diels-Alder cyclization. The method is general to the formation o...

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Bibliographic Details
Published in:Organic letters 2023-12, Vol.25 (48), p.8711-8715
Main Authors: Swift, Elizabeth C, Sales, Zachary S, Wu, Dongpei, Matviitsuk, Anastassia, Pippel, Daniel J, Lebold, Terry P
Format: Article
Language:English
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Summary:A method for the preparation of highly functionalized 4-iodo-7-azaindazoles is reported. These valuable heterocycles are synthesized via condensation of 2-hydrazineylpyrimidines with various iodoalkynones followed by Diels-Alder/retro-Diels-Alder cyclization. The method is general to the formation of products with a variety of C , C , and C substituents while preserving the C iodide functional handle for further late-stage functionalization. The utility of this transformation is demonstrated through the rapid synthesis of several bioactive azaindazole targets.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c03481