Alkynoates as Versatile and Powerful Chemical Tools for the Rapid Assembly of Diverse Heterocycles under Transition-Metal Catalysis: Recent Developments and Challenges.


Journal

Topics in current chemistry (Cham)
ISSN: 2364-8961
Titre abrégé: Top Curr Chem (Cham)
Pays: Switzerland
ID NLM: 101691301

Informations de publication

Date de publication:
05 Jan 2021
Historique:
received: 18 07 2020
accepted: 16 11 2020
entrez: 5 1 2021
pubmed: 6 1 2021
medline: 10 6 2021
Statut: epublish

Résumé

Heterocycles, heteroaromatics and spirocyclic entities are ubiquitous components of a wide plethora of synthetic drugs, biologically active natural products, marketed pharmaceuticals and agrochemical targets. Recognizing their high proportion in drugs and rich pharmacological potential, these invaluable structural motifs have garnered significant interest, thus enabling the development of efficient catalytic methodologies providing access to architecturally complex and diverse molecules with high atom-economy and low cost. These chemical processes not only allow the formation of diverse heterocycles but also utilize a range of flexible and easily accessible building units in a single operation to discover diversity-oriented synthetic approaches. Alkynoates are significantly important, diverse and powerful building blocks in organic chemistry due to their unique and inherent properties such as the electronic bias on carbon-carbon triple bonds posed by electron-withdrawing groups or the metallic coordination site provided by carbonyl groups. The present review highlights the comprehensive picture of the utility of alkynoates (2007-2019) for the synthesis of various heterocycles (> 50 types) using transition-metal catalysts (Ru, Rh, Pd, Ir, Ag, Au, Pt, Cu, Mn, Fe) in various forms. The valuable function of versatile alkynoates (bearing multifunctional groups) as simple and useful starting materials is explored, thus cyclizing with an array of coupling partners to deliver a broad range of oxygen-, nitrogen-, sulfur-containing heterocycles alongside fused-, and spiro-heterocyclic compounds. In addition, these examples will also focus the scope and reaction limitations, as well as mechanistic investigations into the synthesis of these heterocycles. The biological significance will also be discussed, citing relevant examples of drug molecules highlighting each class of heterocycles. This review summarizes the recent developments in the synthetic methods for the synthesis of various heterocycles using alkynoates as readily available starting materials under transition-metal catalysis.

Identifiants

pubmed: 33398642
doi: 10.1007/s41061-020-00316-4
pii: 10.1007/s41061-020-00316-4
doi:

Substances chimiques

Alkynes 0
Heterocyclic Compounds 0
Metals 0
Transition Elements 0

Types de publication

Journal Article Review

Langues

eng

Sous-ensembles de citation

IM

Pagination

3

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Auteurs

Imtiaz Khan (I)

Department of Chemistry, School of Natural Sciences, The University of Manchester, Oxford Road, Manchester, M13 9PL, UK. imtiaz.khan@manchester.ac.uk.
Manchester Institute of Biotechnology, The University of Manchester, 131 Princess Street, Manchester, M1 7DN, UK. imtiaz.khan@manchester.ac.uk.

Aliya Ibrar (A)

Department of Chemistry, Faculty of Natural Sciences, The University of Haripur, Haripur, KPK-22620, Pakistan.

Sumera Zaib (S)

Department of Biochemistry, Faculty of Life Sciences, University of Central Punjab, Lahore, 54590, Pakistan.

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Classifications MeSH