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The Chemistry of Benzotriazole Derivatives pp 143–175Cite as

Benzotriazole-Mediated Synthesis of Oxygen-Containing Heterocycles

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Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 43))

Abstract

This review aims at delivering an overview of the synthetic utility of benzotriazole and its derivatives for the preparation of oxygen-containing heterocycles. This review serves both as a synthetic guide and as a theoretical handbook of benzotriazole-assisted preparations of oxygen heterocycles and offers a complete overview of existing applications for benzotriazole and its derivatives in heterocyclic synthesis. Multiple examples reveal the superiority of benzotriazole-based approaches over conventional ones.

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Abbreviations

(P(C6H5)3)2PdCl2 :

Bis(triphenylphosphine)palladium(II) dichloride

BtH:

1H-1,2,3-Benzotriazole

BuLi:

Butyllithium

CH3CN:

Acetonitrile

DBU:

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

DCM:

Dichloromethane

DMD:

3,3-Dimethyldioxirane

DME:

Dimethoxyethane

DMF:

Dimethylformamide

DMSO:

Dimethylsulfoxide

E:

Electrophile

h:

Hour

Hal:

Halogen

HMPA:

Hexamethylphosphoramide

i-PrOH:

2-Propanol

LDA:

Lithium diisopropylamide

LiHMDS:

Lithium hexamethyldisilazide

m-CPBA:

3-Chloroperbenzoic acid

NIS:

N-Iodosuccinimide

NMP:

N-Methyl-2-pyrrolidone

Py:

Pyridine

rt:

Room temperature

t-BuOH:

tert-Butyl alcohol

t-BuOK:

Potassium tert-butoxide

TFA:

Trifluoroacetic acid

THF:

Tetrahydrofuran

TMSCl:

Trimethylchlorosilane

TsOH:

4-Toluene sulfonic acid

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Authors and Affiliations

  1. South Ural State University, 76, Lenin prospekt, Chelyabinsk, 454080, Russia

    Oleg I. Bolshakov

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  1. Oleg I. Bolshakov
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Correspondence to Oleg I. Bolshakov .

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Editors and Affiliations

  1. Center for Integrated Technology and Organic Synthesis - CiTOS, Department of Chemistry, University of Liège, Liège, Belgium

    Jean-Christophe M. Monbaliu

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Bolshakov, O.I. (2015). Benzotriazole-Mediated Synthesis of Oxygen-Containing Heterocycles. In: Monbaliu, JC. (eds) The Chemistry of Benzotriazole Derivatives. Topics in Heterocyclic Chemistry, vol 43. Springer, Cham. https://doi.org/10.1007/7081_2015_180

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