Solvent‐ and Catalyst‐Free Aza‐Michael Addition of Imidazoles and Related Heterocycles

Katharina Kodolitsch; Florian Gobec; Christian Slugovc

doi:10.1002/ejoc.202000309

Solvent‐ and Catalyst‐Free Aza‐Michael Addition of Imidazoles and Related Heterocycles

Katharina Kodolitsch, Florian Gobec, Christian Slugovc^*

^*Corresponding author for this work

Institute for Chemistry and Technology of Materials (6380)

Research output: Contribution to journal › Article › peer-review

Abstract

This work demonstrates the scope and limitations of the aza-Michael addition of imidazoles and related heterocycles with electron deficient olefins under solvent- and catalyst-free conditions. The reaction proceeds at 80 °C within hours towards completion as long as the azole derivative is sufficiently soluble in the Michael acceptor, which has been used in small excess. Workup only comprises evaporation of surplus Michael-acceptor, and no additional solvents are necessary for purifying the products.

Original language	English
Pages (from-to)	2973-2978
Number of pages	6
Journal	European Journal of Organic Chemistry
Volume	2020
Issue number	19
DOIs	https://doi.org/10.1002/ejoc.202000309
Publication status	Published - 22 May 2020

Keywords

Aza-Michael reaction
Catalyst-free synthesis
Green chemistry
Heterocycles
Solvent-free synthesis

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

Fields of Expertise

Advanced Materials Science

Access to Document

10.1002/ejoc.202000309

Cite this

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title = "Solvent‐ and Catalyst‐Free Aza‐Michael Addition of Imidazoles and Related Heterocycles",

abstract = "This work demonstrates the scope and limitations of the aza-Michael addition of imidazoles and related heterocycles with electron deficient olefins under solvent- and catalyst-free conditions. The reaction proceeds at 80 °C within hours towards completion as long as the azole derivative is sufficiently soluble in the Michael acceptor, which has been used in small excess. Workup only comprises evaporation of surplus Michael-acceptor, and no additional solvents are necessary for purifying the products.",

keywords = "Aza-Michael reaction, Catalyst-free synthesis, Green chemistry, Heterocycles, Solvent-free synthesis",

author = "Katharina Kodolitsch and Florian Gobec and Christian Slugovc",

year = "2020",

month = may,

day = "22",

doi = "10.1002/ejoc.202000309",

language = "English",

volume = "2020",

pages = "2973--2978",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "John Wiley & Sons, Ltd",

number = "19",

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TY - JOUR

T1 - Solvent‐ and Catalyst‐Free Aza‐Michael Addition of Imidazoles and Related Heterocycles

AU - Kodolitsch, Katharina

AU - Gobec, Florian

AU - Slugovc, Christian

PY - 2020/5/22

Y1 - 2020/5/22

N2 - This work demonstrates the scope and limitations of the aza-Michael addition of imidazoles and related heterocycles with electron deficient olefins under solvent- and catalyst-free conditions. The reaction proceeds at 80 °C within hours towards completion as long as the azole derivative is sufficiently soluble in the Michael acceptor, which has been used in small excess. Workup only comprises evaporation of surplus Michael-acceptor, and no additional solvents are necessary for purifying the products.

AB - This work demonstrates the scope and limitations of the aza-Michael addition of imidazoles and related heterocycles with electron deficient olefins under solvent- and catalyst-free conditions. The reaction proceeds at 80 °C within hours towards completion as long as the azole derivative is sufficiently soluble in the Michael acceptor, which has been used in small excess. Workup only comprises evaporation of surplus Michael-acceptor, and no additional solvents are necessary for purifying the products.

KW - Aza-Michael reaction

KW - Catalyst-free synthesis

KW - Green chemistry

KW - Heterocycles

KW - Solvent-free synthesis

UR - https://chemrxiv.org/articles/preprint/Solvent-_and_catalyst-free_aza-Michael_addition_of_imidazoles_and_related_heterocycles/11877039

UR - http://www.scopus.com/inward/record.url?scp=85084419637&partnerID=8YFLogxK

U2 - 10.1002/ejoc.202000309

DO - 10.1002/ejoc.202000309

M3 - Article

SN - 1434-193X

VL - 2020

SP - 2973

EP - 2978

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 19

ER -

Solvent‐ and Catalyst‐Free Aza‐Michael Addition of Imidazoles and Related Heterocycles

Abstract

Keywords

ASJC Scopus subject areas

Fields of Expertise

Access to Document

Other files and links

CD-Laboratory for Organo-Catalysis in Polymerization

Porous Materials @ Work

Cite this

Solvent‐ and Catalyst‐Free Aza‐Michael Addition of Imidazoles and Related Heterocycles

Abstract

Keywords

ASJC Scopus subject areas

Fields of Expertise

Access to Document

Other files and links

Projects

CD-Laboratory for Organo-Catalysis in Polymerization

Porous Materials @ Work

Cite this