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Synthesis of 5-iodo-7-aza-indazole by Diels–Alder cascade and se-lected examples of C–C and C–N cross-coupling reactions

Parmentier, Michael and Hoehn, Pascale and Lanz, Marian and Gallou, Fabrice (2020) Synthesis of 5-iodo-7-aza-indazole by Diels–Alder cascade and se-lected examples of C–C and C–N cross-coupling reactions. Organic process research & development.

Abstract

Although pyrimidines are not among the most reactive partners in intramolecular inverse-electron demand [4s+2s] reactions with alkynes, they could be activat-ed under mild and practical conditions, leading to fused nitrogen-containing heterocycles. We report an opti-mized synthesis of a 5-iodo-7-aza-indazole by a one-pot Diels–Alder cascade that starts from a pyrimidine sub-stituted in the 2-position by an (alkynyl)hydrazone. The safety of the process and the environmental impact were thoroughly evaluated. Eventually, a selection of cross-coupling reactions of 17 was studied and allowed the introduction of carbon- and nitrogen-based nucleophiles at the C5-position in good to excellent yields.

Item Type: Article
Date Deposited: 16 May 2020 00:45
Last Modified: 16 May 2020 00:45
URI: https://oak.novartis.com/id/eprint/42564

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