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Thermal Rearrangements and Transformations of 1,2,3-Triazoles

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Chemistry of 1,2,3-triazoles

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 40))

Abstract

This chapter concentrates on the thermal rearrangements and transformations of 1,2,3-triazoles. It also contains data on the ring-chain tautomerism of 1,2,3-triazoles and the substituent effect on the position of the equilibrium between diazoimines and 1,2,3-triazoles. The main part of this review has been devoted to transition-metal-catalyzed denitrogenative transformation of 1,2,3-triazoles.

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Abbreviations

(R)-{NTV}4 :

αR-α-(isopropyl)-1,3-dioxo-2H-benz[de]isoquinoline-2-acetato

(S)-{NTTL}4 :

αS-α-(tert-butyl)-1,3-dioxo-2H-benz[de]isoquinoline-2-acetato

1,2-DCE:

1,2-Dichloroethane

Alk:

Alkyl

BDPP:

(2R 4R) or (2S, 4S)bis(diphenylphosphino)pentane

Boc:

Benzyloxycarbonyl

CuAAC:

Copper(I)-catalyzed azide–alkyne cycloaddition

DBU:

1,8-Diazabicycloundec-7-ene

DFT:

Density Functional Theory

DMF:

Dimethylformamide

DMSO:

Dimethyl sulfoxide

dr:

Diastereomer ratio

E:

Ester group

ee :

Enantiomer excess

FVP:

Flash Vacuum Pyrolysis

h:

Hour(s)

IR:

Infra-Red

Me:

Methyl

Ms:

Mesyl

MW:

Microwave

n-Bu:

Normal butyl

Ni(cod)2 :

Bis(cyclooctadiene)nickel(0)

NMR:

Nuclear Magnetic Resonance

P(n-Bu)Ad2 :

Di(1-adamantyl)-n-butylphosphine

Ph:

Phenyl

Rh2(esp)2 :

Bis[rhodium(α,α,α′,α′-tetramethyl-1,3-benzenedipropionic acid)]

Rh2(oct)4 :

Rhodium tetra octanoate

Rh2(piv)4 :

Rhodium pivalate

Rh2(S-DOSP)4 :

Tetrakis[(S)-(-)-N-(p-dodecylphenylsulfonyl)prolinato]dirhodium (II)

Rh2(S-PTAD)4 :

Tetrakis[(S)-(+)-(1-adamantyl)-(N-phthalimido)acetato]dirhodium(II)

rt:

Room temperature

TBDMSO:

tert-Butyldimethylsilyloxy

Tf:

Trifluoromethanesulfonyl (triflyl)

Tf2O:

Triflic anhydride

Tpm*,Br :

Tris(3,5-dimethyl-4-bromopyrazolyl)methane]

Ts:

Tosyl 4-toluenesulfonyl

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Acknowledgments

Vasiliy Bakulev and Tetyana Beryozkina thank Russian Foundation for Basic Research (14-03-01033) and State task of Ministry Education No 4.1626.2014/K. Wim Dehaen thanks the FWO-Vlaanderen and the University of Leuven for financial support.

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Authors and Affiliations

  1. Ural Federal University, Mira Str. 19, Yekaterinburg, 620002, Russia

    Vasiliy Bakulev & Tetyana Beryozkina

  2. Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001, Leuven, Belgium

    Wim Dehaen

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  1. Vasiliy Bakulev
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  2. Wim Dehaen
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Correspondence to Vasiliy Bakulev .

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Editors and Affiliations

  1. Department of Chemistry, KU Leuven, Leuven, Belgium

    Wim Dehaen

  2. Ural Federal University, Yekaterinburg, Russia

    Vasiliy A. Bakulev

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Bakulev, V., Dehaen, W., Beryozkina, T. (2014). Thermal Rearrangements and Transformations of 1,2,3-Triazoles. In: Dehaen, W., Bakulev, V. (eds) Chemistry of 1,2,3-triazoles. Topics in Heterocyclic Chemistry, vol 40. Springer, Cham. https://doi.org/10.1007/7081_2014_131

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