Domino Transformations of 3‐Fluoro‐1,2,4‐Triazine Derivatives towards Spirocyclic and Fused Pyridines

Author:

Lapray Anthony1ORCID,Martzel Thomas1,Hiebel Marie‐Aude2,Oudeyer Sylvain1ORCID,Suzenet Franck2,Brière Jean‐François1ORCID

Affiliation:

1. INSA Rouen Normandie Univ Rouen Normandie CNRS Normandie Univ COBRA UMR 6014, INC3M FR 3038 F-76000 Rouen France

2. Université d'Orléans CNRS ICOA UMR 7311 Orléans 45067 France

Abstract

AbstractA domino SNAr‐ihDA/rDA reaction was developed from rarely exploited 3‐fluoro‐1,2,4‐triazines with bifunctional alkyne tethered nucleophiles to construct various fused non‐aromatic/heteroaromatic bicycles in yields ranging from 56 to 99%, notably within the family of valuable spirooxindole derivatives. In this study, the challenging enantioselective phase‐transfer catalyzed arylation of a sulfonyl‐triazine was also demonstrated with up to 66% ee. In both racemic and asymmetric processes, the nature of the leaving group at C3 was key to successfully achieve these sequences.

Funder

Université de Rouen

Région Normandie

Publisher

Wiley

Subject

General Chemistry

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