Abstract

This short review offers a non-exhaustive panorama of the indole ring implicated multicomponent reactions, and simple functional group transformation-based approaches, developed over the last thirty years for the synthesis of various biologically interesting indole heterocyclic ring systems.

Highlights

  • Multicomponent reactions (MCR-s) have recently emerged as valuable tools in the preparation of structurally diverse chemical libraries of drug-like heterocyclic compounds.[1]

  • This review offers a short and non-exhaustive summary of the synthesis of functionalized heterocyclic systems by multicomponent strategies involving indole derivatives as reaction partners

  • Despite the importance of Ugi-type reactions in the synthesis of heterocyclic compounds, only scant attention has been paid to the incorporation of indoles as multicomponent reaction partners

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Summary

Introduction

Multicomponent reactions (MCR-s) have recently emerged as valuable tools in the preparation of structurally diverse chemical libraries of drug-like heterocyclic compounds.[1] The multicomponent reaction story began as far back as 1850 by the publication of the Strecker reaction,[2] arriving nowadays at its apogee During this one and a half century period, some notable achievements include the discovery of the Biginelli,[3] the Mannich,[4] and the Passerini[5] reactions culminating in 1959 when Ugi published[6] probably the most versatile MCR based on the reactivity of isocyanides.[7] In view of the increasing interest for the preparation of large heterocyclic compound libraries, the development of new and synthetically valuable multicomponent reactions remains a challenge for both academic and industrial research teams.[8]. Functionalized indole ring systems have been found frequently in biologically active molecules, indole derivatives as MCR partners are rather under-represented. This review offers a short and non-exhaustive summary of the synthesis of functionalized heterocyclic systems by multicomponent strategies involving indole derivatives as reaction partners

Mannich reaction-“Gramine chemistry”
MCR-s involving isocyanides-Ugi reaction
C NC CN N R
MCR-s with boronic acids-Petasis reaction
Multicomponent reactions using dihydropyridines
Multicomponent reactions combined with domino cyclisation
Yonemitsu-reaction
45 R2:t-Bu R3:CO2Bn 46 R2:H R3:H
51 R: NH2
Conclusions
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