Optimized Synthesis of 7-Azaindazole by a Diels–Alder Cascade and Associated Process Safety
| Autor: | Fabrice Gallou, Nicolas Blanchard, Vincent Le Fouler, Nicolas Brach, Vincent Bizet, Michael Parmentier, Corinne Bailly, Marian Lanz, Pascale Hoehn |
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| Přispěvatelé: | Laboratoire d'innovation moléculaire et applications (LIMA), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS) |
| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
pyrimidine
Pyrimidine 010405 organic chemistry Chemistry process mass intensity Organic Chemistry aza-indazole safety process food and beverages 010402 general chemistry 01 natural sciences Combinatorial chemistry Cycloaddition 0104 chemical sciences chemistry.chemical_compound Cascade Intramolecular force Diels alder [CHIM]Chemical Sciences cas- cade Physical and Theoretical Chemistry cycloaddition |
| Zdroj: | Organic Process Research and Development Organic Process Research and Development, American Chemical Society, 2020, 24 (5), pp.776-786. ⟨10.1021/acs.oprd.0c00184⟩ |
| ISSN: | 1083-6160 1520-586X |
| DOI: | 10.1021/acs.oprd.0c00184⟩ |
| Popis: | International audience; Although pyrimidines are not among the most reactive partners in intramolecular inverse-electron demand [4ps+2ps] reactions with alkynes, they could be activated under mild and practical conditions, leading to fused nitrogen-containing heterocycles. We report an optimized synthesis of a 5-iodo-7-aza-indazole by a one-pot Diels-Alder cascade that starts from a pyrimidine substituted 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. |
| Databáze: | OpenAIRE |
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