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Flow-Assisted Synthesis of Heterocycles via Multicomponent Reactions

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Flow Chemistry for the Synthesis of Heterocycles

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 56))

Abstract

Multicomponent reactions (MCRs) are of great significance in organic synthesis. They often decrease the number of synthesis steps since three or more reactants are incorporated in the product in a single step. This increases the number of combinatorial options and allows more efficient processes in less time. The pharmaceutical industry is therefore very fond of MCRs for the construction of libraries. As a consequence, the field is being investigated intensely for the enhancement of chemical processes and the discovery of new types of MCRs.

The combination of the benefits of flow technology and MCRs for heterocycle synthesis is an interesting and specialized field. This chapter serves as an overview of the literature covering this topic starting from 2010, up to when the literature on this matter is reviewed in a book chapter in this book series by Cukalovic et al. (Top Heterocycl Chem 23:161–198, 2010).

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Abbreviations

2-MeTHF:

2-Methyltetrahydrofuran

AcOH:

Acetic acid

Boc:

tert-Butoxycarbonyl

BPR:

Back-pressure regulator

DBU:

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

DCM:

Dichloromethane

DIPEA:

N,N-Diisopropylethylamine

DMA:

N,N-Dimethylacetamide

DMAP:

4-Dimethylaminopyridine

DME:

1,2-Dimethoxyethane

DMF:

N,N-Dimethylformamide

EDC:

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

eq:

Equivalents

Et2O:

Diethyl ether

Et3N:

Triethylamine

EtOAc:

Ethyl acetate

EtOH:

Ethanol

HOBt:

1-Hydroxybenzotriazole

kHz:

Kilohertz

M:

Molar

MCR:

Multicomponent reaction

MeCN:

Acetonitrile

MeOH:

Methanol

MW:

Microwave

PEG200:

Polyethylene glycol 200

PEG300:

Polyethylene glycol 300

PFA:

Perfluoroalkoxy alkane

psi:

Pound-force per square inch

PTFE:

Polytetrafluoroethylene (Telfon®)

t-BuONO:

tert-Butyl nitrite

TMSN3 :

Trimethylsilyl azide

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Authors and Affiliations

  1. Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Leuven, Belgium

    Seger Van Mileghem, Cedrick Veryser & Wim M. De Borggraeve

Authors
  1. Seger Van Mileghem
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  2. Cedrick Veryser
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  3. Wim M. De Borggraeve
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Corresponding author

Correspondence to Wim M. De Borggraeve .

Editor information

Editors and Affiliations

  1. Department of Chemistry, University of Leuven (KU Leuven), Leuven, Belgium

    Upendra K. Sharma

  2. Department of Chemistry, University of Leuven (KU Leuven), Leuven, Belgium

    Erik V. Van der Eycken

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Van Mileghem, S., Veryser, C., De Borggraeve, W.M. (2018). Flow-Assisted Synthesis of Heterocycles via Multicomponent Reactions. In: Sharma, U., Van der Eycken, E. (eds) Flow Chemistry for the Synthesis of Heterocycles. Topics in Heterocyclic Chemistry, vol 56. Springer, Cham. https://doi.org/10.1007/7081_2018_23

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