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Indole as a Versatile Building Block in Cycloaddition Reactions: Synthesis of Diverse Heterocyclic Frameworks

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Abstract

Indole, a ubiquitous and structurally versatile aromatic compound, has emerged as a key player in the synthesis of diverse heterocyclic frameworks via cycloaddition reactions. These reactions are completely atom-economical and, hence, are considered as green reactions. This review article provides a comprehensive overview of the pivotal role played by indole in the construction of complex and biologically relevant heterocyclic compounds. Here we explore the chemistry of indole-based cycloadditions, highlighting their synthetic utility in accessing a wide array of heterocyclic architectures, including cyclohepta[b]indoles, tetrahydrocarbazoles, tetrahydroindolo[3,2-c]quinoline, and indolines, among others. Additionally, we discuss the mechanistic insights that underpin these transformations, emphasizing the strategic importance of indole as a building block. The content of this article will certainly encourage the readers to explore more work in this area.

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Data availability

The data reported in this review article is available in the original paper mentioned in the references.

Abbreviations

Ac:

Acetyl

°C:

Degree centigrade

Cat.:

Catalyst

CHD:

Cyclohexylidene

CPA:

Chiral phosphoric acid

DCM:

Dichloromethane

DMF:

Dimethylformamide

DMAP:

4-(Dimethylamino)pyridine

DMSO:

Dimethylsulfoxide

d.r.:

Diastereomeric ratio

EDG:

Electron-donating group

EWG:

Electron-withdrawing group

eq.:

Equivalent

h:

Hour

iPr:

Iso Propyl

LED:

Light-emitting diode

MeOH:

Methanol

min:

Minutes

Me:

Methyl

MS:

Molecular sieve

r.t.:

Room temperature

TFE:

Trifluoroethanol

THF:

Tetrahydrofuran

tBu:

tertiary Butyl

W:

Watt

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Acknowledgements

The author MLD acknowledge the University of Science and Technology, Meghalaya, for the library facility, and BB acknowledge Pandu College for the same.

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Authors and Affiliations

  1. Department of Chemistry, Pandu College, Guwahati, Assam, 781012, India

    Biswajita Baruah

  2. Department of Chemistry, Madhabdev University, Lakhimpur, Assam, 784164, India

    Choitanya Dev Pegu

  3. Advanced Research Centre and Department of Chemistry, University of Science and Technology Meghalaya, Ri-Bhoi, Meghalaya, 793101, India

    Mohit L. Deb

Authors
  1. Biswajita Baruah
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  2. Choitanya Dev Pegu
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  3. Mohit L. Deb
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Correspondence to Biswajita Baruah or Mohit L. Deb.

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Baruah, B., Pegu, C.D. & Deb, M.L. Indole as a Versatile Building Block in Cycloaddition Reactions: Synthesis of Diverse Heterocyclic Frameworks. Top Curr Chem (Z) 382, 18 (2024). https://doi.org/10.1007/s41061-024-00463-y

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