Development of a DABCO-Succinic Acid Based Catalytic System for the Aza-Michael Addition and Aza-Michael/Knoevenagel Tandem Reaction of Thiazolidine-2,4-dione to Electron Deficient Alkenes

Kilsoo Jung; Sunmi Kim; Seonghwi Choi; Ikyon Kim; Gyoonhee Han

doi:10.1021/acs.joc.1c02003

Development of a DABCO-Succinic Acid Based Catalytic System for the Aza-Michael Addition and Aza-Michael/Knoevenagel Tandem Reaction of Thiazolidine-2,4-dione to Electron Deficient Alkenes

Kilsoo Jung, Sunmi Kim, Seonghwi Choi, Ikyon Kim, Gyoonhee Han

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

2 Citations (Scopus)

Abstract

A DABCO catalyzed aza-Michael addition of thiazolidine-2,4-dione to a variety of electron deficient alkenes has been developed. Additionally, a DABCO/succinic acid salt system has been designed that allows for the one pot tandem aza-Michael/Knoevenagel reaction of thiazolidine-2,4-dione to give difunctionalized thiazolidine-2,4-dione products. To the best of our knowledge, this is the first example of a one-pot tandem aza-Michael/Knoevenagel reaction involving thiazolidine-2,4-dione.

Original language	English
Pages (from-to)	16785-16794
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	86
Issue number	23
DOIs	https://doi.org/10.1021/acs.joc.1c02003
Publication status	Published - 2021 Dec 3

Bibliographical note

Funding Information:
We thank the National Research Foundation of Korea (Grants NRF-2018R1A6A1A03023718 and NRF-2020R1A2C2005961) for generous financial support

Publisher Copyright:
© 2021 American Chemical Society

All Science Journal Classification (ASJC) codes

Organic Chemistry

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title = "Development of a DABCO-Succinic Acid Based Catalytic System for the Aza-Michael Addition and Aza-Michael/Knoevenagel Tandem Reaction of Thiazolidine-2,4-dione to Electron Deficient Alkenes",

abstract = "A DABCO catalyzed aza-Michael addition of thiazolidine-2,4-dione to a variety of electron deficient alkenes has been developed. Additionally, a DABCO/succinic acid salt system has been designed that allows for the one pot tandem aza-Michael/Knoevenagel reaction of thiazolidine-2,4-dione to give difunctionalized thiazolidine-2,4-dione products. To the best of our knowledge, this is the first example of a one-pot tandem aza-Michael/Knoevenagel reaction involving thiazolidine-2,4-dione.",

author = "Kilsoo Jung and Sunmi Kim and Seonghwi Choi and Ikyon Kim and Gyoonhee Han",

note = "Funding Information: We thank the National Research Foundation of Korea (Grants NRF-2018R1A6A1A03023718 and NRF-2020R1A2C2005961) for generous financial support Publisher Copyright: {\textcopyright} 2021 American Chemical Society",

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doi = "10.1021/acs.joc.1c02003",

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Development of a DABCO-Succinic Acid Based Catalytic System for the Aza-Michael Addition and Aza-Michael/Knoevenagel Tandem Reaction of Thiazolidine-2,4-dione to Electron Deficient Alkenes. / Jung, Kilsoo; Kim, Sunmi; Choi, Seonghwi et al.

In: Journal of Organic Chemistry, Vol. 86, No. 23, 03.12.2021, p. 16785-16794.

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

TY - JOUR

T1 - Development of a DABCO-Succinic Acid Based Catalytic System for the Aza-Michael Addition and Aza-Michael/Knoevenagel Tandem Reaction of Thiazolidine-2,4-dione to Electron Deficient Alkenes

AU - Jung, Kilsoo

AU - Kim, Sunmi

AU - Choi, Seonghwi

AU - Kim, Ikyon

AU - Han, Gyoonhee

N1 - Funding Information: We thank the National Research Foundation of Korea (Grants NRF-2018R1A6A1A03023718 and NRF-2020R1A2C2005961) for generous financial support Publisher Copyright: © 2021 American Chemical Society

PY - 2021/12/3

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AB - A DABCO catalyzed aza-Michael addition of thiazolidine-2,4-dione to a variety of electron deficient alkenes has been developed. Additionally, a DABCO/succinic acid salt system has been designed that allows for the one pot tandem aza-Michael/Knoevenagel reaction of thiazolidine-2,4-dione to give difunctionalized thiazolidine-2,4-dione products. To the best of our knowledge, this is the first example of a one-pot tandem aza-Michael/Knoevenagel reaction involving thiazolidine-2,4-dione.

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Development of a DABCO-Succinic Acid Based Catalytic System for the Aza-Michael Addition and Aza-Michael/Knoevenagel Tandem Reaction of Thiazolidine-2,4-dione to Electron Deficient Alkenes

Abstract

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