Organometallic methods for the synthesis and functionalization of azaindoles.

  title={Organometallic methods for the synthesis and functionalization of azaindoles.},
  author={Jinhua J. Song and Jonathan T. Reeves and Fabrice Gallou and Zhulin Tan and Nathan Yee and Chris Hugh Senanayake},
  journal={Chemical Society reviews},
  volume={36 7},
Azaindoles (also called pyrrolopyridines) constitute essential subunits in many pharmaceutically important compounds. The synthesis of azaindoles has been a great synthetic challenge for chemists. Many classical methods for indole synthesis (such as Fischer and Madelung cyclizations) often cannot be effectively applied to the synthesis of the corresponding azaindoles. In recent years, advances in organometallic chemistry have enabled a number of novel and efficient methodologies for azaindole… 

Metal-Catalyzed Cross-Coupling Reactions on Azaindole Synthesis and Functionalization

This paper highlights the diverse synthetic methodologies developed to date involving metal-catalyzed reaction to attain azaindoles and its functionalization and its challenging synthesis and relevant bioactivity.

Synthesis of polysubstituted 5-azaindoles via palladium-catalyzed heteroannulation of diarylalkynes.

A general and efficient procedure for the synthesis of functionalized 5-azaindoles through the catalyzed heteroannulation of 4-acetamido-3-iodopyridines and diarylalkynes is described. The reaction

Recent advances in organocatalytic methods for the synthesis of disubstituted 2- and 3-indolinones.

This review aims to cover the literature on asymmetric quaternary carbons, 2-substituted and 2,2'-disubtituted 3-indolinones, from its origin to the end of 2011.

Regioselective deoxygenative chalcogenation of 7-azindole N-oxides promoted by I2/PEG-200.

A general and sustainable approach for the regioselective deoxygenative chalcogenation of 7-azindole N-oxides with broad substrate scope, green reaction conditions, and operational simplicity is developed.

Progress in palladium-based catalytic systems for the sustainable synthesis of annulated heterocycles: a focus on indole backbones.

This critical review clearly indicates that the development of ligand chemistry, mainly phosphines and carbenes, in the last few decades gave a significant impetus to powerful functionalization of indoles at virtually all positions of this ubiquitous backbone.

A Flexible Convergent Route to Azaoxindoles, Azaindolines, Azaindoles, and Tetrahydroazaquinolones

A variety of azaoxindoles, azaindolines, azaindoles, and tetrahydroazaquinolones can be readily prepared by cyclisation onto pyridine rings of radicals derived from xanthates. The xanthate precursors

Access to Highly Substituted 7-Azaindoles from 2-Fluoropyridines via 7-Azaindoline Intermediates.

A versatile synthesis of 7-azaindoles from substituted 2-fluoropyridines is described, and optional regioselective electrophilic C5-substitution and subsequent in situ oxidation delivers highly functionalized 7-azardoles in high overall efficiency.

Recent Progress on the Synthesis of (Aza)indoles through Oxidative Alkyne Annulation Reactions

The oxidative [3+2] cycloaddition of alkynes with arylamines is a powerful method for the synthesis of (aza)indoles because it employs unfunctionalized and easily available materials. Herein, recent



Efficient access to azaindoles and indoles.

An expedient, catalytic method for the synthesis of diverse azaindoles and indoles, starting from readily available and inexpensive starting materials, is described.

Synthesis of Tetracyclic 5-Azaindole Analogues by Palladium-Catalyzed Sequential Annulation

Tetracyclic 5-azaindole analogues were prepared by palla dium-catalyzed sequential annulation of benzylidene(3-iodopyridinyl-4-yl)amine and 1-aryl substituted internal alkynes under Pd(OAc) 2,

Carbolithiation of Vinyl Pyridines as a Route to 7‐Azaindoles.

An effective synthesis of the 7-azaindole ring system has been developed from substituted 2-amino-3-vinyl pyridines. The methodology involves a novel cascade reaction sequence of controlled

A versatile synthesis of 7-azaindoles

1,3-Disubstituted 7-azaindoles were synthesized from 2,6-dichloropyridine using DoM and intramolecular aromatic substitution after epoxide opening by an amine. Even the sterically demanding

A novel and direct synthesis of indoles via catalytic reductive annulation of nitroaromatics with alkynes.

Indoles are produced regioselectively and in moderate yields from the reactions of nitroaromatics with alkynes catalyzed by [CpM(CO)2]2 under carbon monoxide.