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

被引：7

作者：

Lam, Bao Vy ^{[1
,2
]}

Berhault, Yohann ^{[1
,2
]}

Stiebing, Silvia ^{[1
,2
]}

Fossey, Christine ^{[1
,2
]}

Cailly, Thomas ^{[1
,2
]}

Collot, Valerie ^{[1
,2
]}

Fabis, Frederic ^{[1
,2
]}

机构：

[1] Normandie Univ, Caen, France

[2] Univ Caen Normandie, CERMN, UFR Sci Pharmaceut, EA 4258,FR CNRS 3038,INC3M SF ICORE 4206, Bd Becquerel,CS 14032, Caen 5, France

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 13期

关键词：

heterocycles; magnesium; metalation; regioselectivity; synthetic methods; NITRIC-OXIDE SYNTHASE; N BOND FORMATION; ANTITUMOR-ACTIVITY; COUPLING REACTIONS; KINASE INHIBITOR; DERIVATIVES; 3-IODOINDAZOLES; 1H-INDAZOLES; ANTAGONISTS; AMINATION;

D O I：

10.1002/chem.201504828

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 TMPMgClLiCl (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.

引用

页码：4440 / 4446

页数：7

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