title: Iodoindazoles with Selective Magnesiation at Position 3: A Route to Highly Functionalized Indazoles.
abstract: 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.
authors.affiliation: Normandie Université, France.|Université de Caen Normandie, CERMN (EA 4258 - FR CNRS 3038 INC3M - SF 4206 ICORE), UFR des Sciences Pharmaceutiques, Bd Becquerel, CS, 14032, Caen cedex 5, France.
authors.forename: Bao Vy
authors.initials: BV
authors.lastname: Lam
authors.affiliation: Normandie Université, France.|Université de Caen Normandie, CERMN (EA 4258 - FR CNRS 3038 INC3M - SF 4206 ICORE), UFR des Sciences Pharmaceutiques, Bd Becquerel, CS, 14032, Caen cedex 5, France.
authors.forename: Yohann
authors.initials: Y
authors.lastname: Berhault
authors.affiliation: Normandie Université, France.|Université de Caen Normandie, CERMN (EA 4258 - FR CNRS 3038 INC3M - SF 4206 ICORE), UFR des Sciences Pharmaceutiques, Bd Becquerel, CS, 14032, Caen cedex 5, France.
authors.forename: Silvia
authors.initials: S
authors.lastname: Stiebing
authors.affiliation: Normandie Université, France.|Université de Caen Normandie, CERMN (EA 4258 - FR CNRS 3038 INC3M - SF 4206 ICORE), UFR des Sciences Pharmaceutiques, Bd Becquerel, CS, 14032, Caen cedex 5, France.
authors.forename: Christine
authors.initials: C
authors.lastname: Fossey
authors.affiliation: Normandie Université, France.|Université de Caen Normandie, CERMN (EA 4258 - FR CNRS 3038 INC3M - SF 4206 ICORE), UFR des Sciences Pharmaceutiques, Bd Becquerel, CS, 14032, Caen cedex 5, France.
authors.forename: Thomas
authors.initials: T
authors.lastname: Cailly
authors.affiliation: Normandie Université, France. valerie.collot@unicaen.fr.|Université de Caen Normandie, CERMN (EA 4258 - FR CNRS 3038 INC3M - SF 4206 ICORE), UFR des Sciences Pharmaceutiques, Bd Becquerel, CS, 14032, Caen cedex 5, France. valerie.collot@unicaen.fr.
authors.forename: Valérie
authors.initials: V
authors.lastname: Collot
authors.affiliation: Normandie Université, France. frederic.fabis@unicaen.fr.|Université de Caen Normandie, CERMN (EA 4258 - FR CNRS 3038 INC3M - SF 4206 ICORE), UFR des Sciences Pharmaceutiques, Bd Becquerel, CS, 14032, Caen cedex 5, France. frederic.fabis@unicaen.fr.
authors.forename: Frédéric
authors.initials: F
authors.lastname: Fabis
keywords: heterocycles; magnesium; metalation; regioselectivity; synthetic methods