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Aminoazoles as Key Reagents in Multicomponent Heterocyclizations

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Synthesis of Heterocycles via Multicomponent Reactions I

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 23))

Abstract

Because of the significant role in biological processes in living cells and the diverse types of physiological activities, heterocyclic compounds are in focus of intense investigations by academic and applied-oriented chemists. Considerably, a scientific renaissance of heterocycles during the last decades is closely related to the development of multicomponent approaches to their synthesis. Multicomponent methodology fundamentally different from two-component or sequential processes together with other innovative synthetic methods like microwave- and ultrasonic-assisted reactions offer some new possibilities in constructing heterocyclic systems with high level of molecular diversity and complexity. An overview of known multicomponent heterocyclizations using aminoazoles as a key reagent and their rich synthetic potential for obtaining five-, six-, and seven-membered heterocycles is presented. A special attention is paid to the tuning of chemo- and regio- and positional selectivity of some reactions as well as to the application of nonclassical activation methods based on microwave and ultrasonic irradiation.

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Abbreviations

3-CR:

Three-component reaction

DMF:

Dimethylformamide

DMSO:

Dimethylsulfoxide

MCR:

Multicomponent reaction

MW:

Microwave

NMR:

Nuclear magnetic resonance

p-TSA:

para-Toluene sulfonic acid

RT:

Reverse transcriptase

SAR:

Structure-activity relationship

US:

Ultrasonication

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Acknowledgments

The authors thank University of Konstanz and personally Prof. U. Groth for allowing to access scientific databases, electronic and university libraries.

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Authors and Affiliations

  1. State Scientific Institution “Institute for Single Crystals” of National Academy of Sciences of Ukraine, Lenin Ave, 60, 61001, Kharkiv, Ukraine

    Valentin A. Chebanov & Sergey M. Desenko

  2. University of Konstanz, Fachbereich Chemie, Fach M-720, Universitaetsstrasse 10, 78457, Konstanz, Germany

    Katerina A. Gura

Authors
  1. Valentin A. Chebanov
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  2. Katerina A. Gura
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  3. Sergey M. Desenko
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Corresponding author

Correspondence to Valentin A. Chebanov .

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Editors and Affiliations

  1. Fac. Sciences, Dept. Chemistry &, VU University Amsterdam, De Boelelaan 1083, Amsterdam, 1081 HV, Netherlands

    Romano V. A. Orru

  2. Faculty of Sciences, Section of Synthetic &, VU University Amsterdam, Amsterdam, 1081 HV, Netherlands

    Eelco Ruijter

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Chebanov, V.A., Gura, K.A., Desenko, S.M. (2010). Aminoazoles as Key Reagents in Multicomponent Heterocyclizations. In: Orru, R., Ruijter, E. (eds) Synthesis of Heterocycles via Multicomponent Reactions I. Topics in Heterocyclic Chemistry, vol 23. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2009_21

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