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Article Dans Une Revue Organic Letters Année : 2023

Divergent Synthesis of 6- or 7-Aza-Indazoles via Intramolecular Diels–Alder Cascade of Pyrazines

Résumé

Pyrazines are reactive 4π partners in intermolecular Diels–Alder cycloaddition with exceptionally activated dienophiles or in an intermolecular version at elevated temperatures. Herein, it is shown that an intramolecular cascade could occur even at room temperature, delivering a collection of 6- or 7-aza-indazoles. An interesting substituent effect of the cycloaddition precursor on the product distribution was uncovered, and in situ NMR studies were conducted to gain insights into this unexpected selectivity.

Domaines

Chimie
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Dates et versions

hal-04262921 , version 1 (31-10-2023)

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Nicolas Brach, Lucas Popek, Mathieu Truong, Claire Laurent, Vincent Bizet, et al.. Divergent Synthesis of 6- or 7-Aza-Indazoles via Intramolecular Diels–Alder Cascade of Pyrazines. Organic Letters, In press, ⟨10.1021/acs.orglett.3c03052⟩. ⟨hal-04262921⟩
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