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Article Dans Une Revue Chemistry - A European Journal Année : 2016

Iodoindazoles with Selective Magnesiation at Position 3: A Route to Highly Functionalized Indazoles

Résumé

A unique route to highly functionalized indazoles is described. A regioselective magnesiation at position 3 of 4-, 5-, 6- and 7-iodo-2-THP-indazoles (THP=tetrahydropyranyl) has been developed using TMPMgCl⋅LiCl (TMP=2,2,6,6-tetramethylpiperidyl). The obtained magnesiate can be trapped by different electrophiles to introduce a wide range of functional groups including halogens, thioalkyls, alcohols, aldehydes, ketones, amides, or esters at position 3. Once this position is functionalized, the iodine atoms can be further reacted through metal-halogen exchange or cross-coupling strategies. Finally, N-substitution reactions allow the synthesis of a variety of highly functionalized indazoles giving access to these valuable scaffolds through a simple and unique route

Domaines

Chimie organique

Dates et versions

hal-02043771 , version 1 (21-02-2019)

Identifiants

Citer

Bao Vy Lam, Yohann Berhault, Silvia Stiebing, Christine Fossey, Thomas Cailly, et al.. Iodoindazoles with Selective Magnesiation at Position 3: A Route to Highly Functionalized Indazoles. Chemistry - A European Journal, 2016, 22 (13), pp.4440-4446. ⟨10.1002/chem.201504828⟩. ⟨hal-02043771⟩
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