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Oxime Esters: Flexible Building Blocks for Heterocycle Formation

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Abstract

Oxime esters as the applicable building blocks, internal oxidizing agents, and directing groups in the synthesis of –, S-, and O-containing heterocycle scaffolds have gained great attention in the last decade. This review provides an overview of recent advances in the cyclization of oxime esters with various functional group reagents under transition metal and transition metal-free catalyzed conditions. Moreover, the mechanistic aspects of these protocols are explained in detail.

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Abbreviations

SET:

Single electron transfer

DMSO:

Dimethyl sulfoxide

DBU:

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

DMA:

Dimethylacetamide

DCE:

1,2-Dichloroethane

TEMPO:

(2,2,6,6-Tetramethylpiperidin-1-yl)oxyl

DMF:

Dimethylformamide

DCM:

Dichloroethane

EWG:

Electron-withdrawing group

TEA:

Triethylamine

IMPDH:

Inosine-5′-monophosphatase dehydrogenase

Py:

Pyridine

NMP:

N-methyl-2-pyrrolidone

EDC:

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide

PivOH:

Pivalic acid

THF:

Tetrahydrofuran

TBD:

Triazabicyclodecene

TM:

Transition metal

SCE:

Saturated calomel electrode

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Authors and Affiliations

  1. School of Chemistry, College of Science, University of Tehran, Tehran, Iran

    Faeze Yousefnejad & Fatemeh Gholami

  2. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran

    Bagher Larijani & Mohammad Mahdavi

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Yousefnejad, F., Gholami, F., Larijani, B. et al. Oxime Esters: Flexible Building Blocks for Heterocycle Formation. Top Curr Chem (Z) 381, 17 (2023). https://doi.org/10.1007/s41061-023-00431-y

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