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

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Abstract

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.

Graphic Abstract

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.

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Abbreviations

acac:

Acetylacetonate

AD:

Alzheimer’s disease

AMP:

Adenosine monophosphate

BACE:

1 Beta-secretase 1, beta-site amyloid precursor protein cleaving enzyme 1

BDMS:

Bromodimethylsulfonium bromide

Boc:

tert-Butoxycarbonyl

bdpp:

2,4-Bis(diphenylphosphino)pentane

BINAP:

2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl

bmim:

1-Buyl-3-methylimidazolidin

Bn:

Benzyl

bpy:

2,2′-Bipyridine

BQ:

Benzoquinone

BPO:

Benzoyl peroxide

BZD:

Benzodiazepine

CAN:

Cerium ammonium nitrate

CM:

Cross-metathesis

CNS:

Central nervous system

COD:

1,5-Cyclooctadiene

Cp*:

Pentamethylcyclopentadienyl

CPT:

Camptothecin

DABCO:

1,4-Diazabicyclo[2.2.2]octane

DAN:

Diazoacetonitrile

dba:

Dibenzylideneacetone

DBU:

1,8-Diazabicyclo[5.4.0]undec-7-ene

DCE:

1,2-Dichloroethane

DCM:

Dichloromethane

DDQ:

2,3-Dichloro-5,6-dicyano-1,4-quinone

DEAD:

Diethyl acetylenedicarboxylate

DHP:

Dihydropyridine

DIPEA:

Diisopropylethylamine

DM:

Diabetes mellitus

DMA:

N,N-Dimethylacetamide

DME:

Dimethyl ether

DMF:

N,N-Dimethylformamide

DMAD:

Dimethyl acetylenedicarboxylate

DMSO:

Dimethyl sulfoxide

dppb:

1,4-Bis(diphenylphosphino)butane

dppf:

1,1′-Ferrocenediyl-bis(diphenylphosphine)

dppp:

Diphenylpropylendiphosphine

dtbbpy:

4,4′-Di-tert-butyl-2,2′-bipyridine

DTBP:

Di-tert-butylperoxide

EDG:

Electron-donating group

equiv:

Equivalent

EWG:

Electron-withdrawing group

Hex:

Hexyl

HFIP:

Hexafluoroisopropanol

HIV:

Human immunodeficiency virus

IMDA:

Intramolecular Diels–Alder

KHMDS:

Potassium bis(trimethylsilyl)amide

L:

Ligand

LED:

Light-emitting diode

MOM:

Methoxymethyl

MS:

Molecular sieves

MTBE:

Methyl tertiart butyl ether

NaBARF:

Sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate

NBE:

Norbornenes

NIS:

N-Iodosuccinimide

NMP:

N-Methylpyrrolidinone

PD:

Parkinson’s disease

PDE:

Phosphodiesterase

Pent:

Pentyl

Ph:

Phenyl

PIDA:

Phenyliodine(III) diacetate

1,10-phen:

1,10-Phenanthroline

PPO:

4H-Pyrido[1,2-a]pyrimidin-4-one

ppy:

2-Phenylpyridinato

PTSA:

p-Toluenesulfonic acid

RCM:

Ring-closing metathesis

rt:

Room temperature

SET:

Single-electron-transfer

TBAI:

Tetrabutylammonium iodide

TBHP:

tert-Butyl hydroperoxide

TBS:

tert-Butyldimethylsilyl

TDMPP:

Tris(2,6-dimethoxyphenyl)phosphine

TEMPO:

2,2,6,6-Tetramethyl-1-piperidinyloxy

TES:

Triethylsilyl

TFA:

Trifluoroacetic acid

TFE:

Trifluoroethanol

THF:

Tetrahydrofuran

THP:

Tetrahydropyranyl

TMS:

Trimethylsilyl

TXA2 :

Thromboxane A2

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Authors and Affiliations

  1. Department of Chemistry, School of Natural Sciences, The University of Manchester, Oxford Road, Manchester, M13 9PL, UK

    Imtiaz Khan

  2. Manchester Institute of Biotechnology, The University of Manchester, 131 Princess Street, Manchester, M1 7DN, UK

    Imtiaz Khan

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

    Aliya Ibrar

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

    Sumera Zaib

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Khan, I., Ibrar, A. & Zaib, S. Alkynoates as Versatile and Powerful Chemical Tools for the Rapid Assembly of Diverse Heterocycles under Transition-Metal Catalysis: Recent Developments and Challenges. Top Curr Chem (Z) 379, 3 (2021). https://doi.org/10.1007/s41061-020-00316-4

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