Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Metal-free annulation of arenes with 2-aminopyridine derivatives: the methyl group as a traceless non-chelating directing group.

Literature DB >> 24938862

Metal-free annulation of arenes with 2-aminopyridine derivatives: the methyl group as a traceless non-chelating directing group.

Srimanta Manna¹, Kiran Matcha, Andrey P Antonchick.

Abstract

A novel annulation reaction between 2-aminopyridine derivatives and arenes under metal-free conditions is described. The presented intermolecular transformation provided straightforward access to the important pyrido[1,2-a]benzimidazole scaffold under mild reaction conditions. The unprecedented application of the methyl group of methylbenzenes as a traceless, non-chelating, and highly regioselective directing group is reported.

Entities: Chemical

Keywords: CH amination; annulation; benzimidazoles; hypervalent iodine reagents; metal-free reactions

Mesh：

Substances：

Year: 2014 PMID： 24938862 DOI： 10.1002/anie.201403712

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

Keyword Cloud
Cited

8 in total

1. Ι₂-mediated amination/cyclization of ketones with 2-aminopyridines under high-speed ball milling: solvent- and metal-free synthesis of 2,3-substituted imidazo[1,2-a]pyridines and zolimidine.

Authors: Fang-Jian Wang; Hui Xu; Ming Xin; Ze Zhang
Journal: Mol Divers Date: 2016-03-14 Impact factor: 2.943

2. Regiospecific N-Arylation of Aliphatic Amines under Mild and Metal-Free Reaction Conditions.

Authors: Nibadita Purkait; Gabriella Kervefors; Erika Linde; Berit Olofsson
Journal: Angew Chem Int Ed Engl Date: 2018-07-26 Impact factor: 15.336

3. Electrooxidative para-selective C-H/N-H cross-coupling with hydrogen evolution to synthesize triarylamine derivatives.

Authors: Kun Liu; Shan Tang; Ting Wu; Shengchun Wang; Minzhu Zou; Hengjiang Cong; Aiwen Lei
Journal: Nat Commun Date: 2019-02-07 Impact factor: 14.919

Metal-free annulation of arenes with 2-aminopyridine derivatives: the methyl group as a traceless non-chelating directing group.

1. Ι₂-mediated amination/cyclization of ketones with 2-aminopyridines under high-speed ball milling: solvent- and metal-free synthesis of 2,3-substituted imidazo[1,2-a]pyridines and zolimidine.

2. Regiospecific N-Arylation of Aliphatic Amines under Mild and Metal-Free Reaction Conditions.

3. Electrooxidative para-selective C-H/N-H cross-coupling with hydrogen evolution to synthesize triarylamine derivatives.

4. Molecular mechanism of azoxy bond formation for azoxymycins biosynthesis.

5. Hypervalent iodine promoted the synthesis of cycloheptatrienes and cyclopropanes.

6. Iodine-mediated oxythiolation of o-vinylanilides with disulfides for the synthesis of benzoxazines.

7. [1+1+1] Cyclotrimerization for the Synthesis of Cyclopropanes.

8. Mechanism of the Dehydrogenative Phenothiazination of Phenols.