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; Kim, Ikyon; Han, Gyoonhee

doi:10.1021/acs.joc.1c02003

Cited by 6 publications

(4 citation statements)

References 36 publications

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“…In light of the respective pKa of DABCO and HCO 2 H, the in situ generated HCO 2 H could be trapped by DABCO to form the DABCO-formate, which might be the catalytic system to start another catalytic cycle via a similar mechanism depicted in Scheme 5 (cycle B). To test this hypothesis, we prepared the DABCO-formate according to the literature procedure (Scheme 5, eq1), [20] and test it as the catalyst in the reaction of 1 a with 2 a. It was found that the reaction proceeded smoothly to give target compound 3 a in 45% yield (Scheme 5, eq2).…”

Section: Resultsmentioning

confidence: 99%

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DABCO‐Catalysed [3+2] Cyclization/Deformylation Cascade of p‐Quinols with 3‐Formylchromones: Access to Benzopyrone‐Fused Tetracyclic Ring Systems

et al. 2023

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The construction of benzopyrone‐fused hydrobenzofuranones via DABCO‐catalyzed [3+2] cyclization/deformylation cascade of p‐quinols with 3‐formylchromones is described. The reaction works under mild reaction conditions to provide the desired products in 53–90% yields with complete diastereoselectivities. In addition, an enantioselective version with 81% ee is also realized in the presence of Takemoto's chiral thiourea catalyst.

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Section: Resultsmentioning

confidence: 99%

“…This is consistent with the literature reports that DABCO salts derived from carboxylic acid can be used as the Brønsted base to catalyze (aza)Michael reaction. [20]…”

Section: Resultsmentioning

confidence: 99%

DABCO‐Catalysed [3+2] Cyclization/Deformylation Cascade of p‐Quinols with 3‐Formylchromones: Access to Benzopyrone‐Fused Tetracyclic Ring Systems

et al. 2023

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“…One of the rare examples of such transformation has been very recently described. [84] Authors show that thiazolidine-2,4-dione do not react with α,β-unsaturated esters, amides, enones and sulfone in the presence of mineral (K 2 CO 3 ) or several organic bases (TEA, DBN, DBU, quinuclidine). In these cases, trace of adducts or complex mixture of unidentified products are formed.…”

Section: Amides Carbamates Hydrazides and Uracilesmentioning

confidence: 99%

“…Communications on the aza‐Michael addition of thiazolidine‐2,4‐dione derivatives are scarce. One of the rare examples of such transformation has been very recently described [84] . Authors show that thiazolidine‐2,4‐dione do not react with α,β‐unsaturated esters, amides, enones and sulfone in the presence of mineral (K 2 CO 3 ) or several organic bases (TEA, DBN, DBU, quinuclidine).…”

Section: Amides Carbamates Hydrazides and Uracilesmentioning

confidence: 99%

Weak Nucleophiles in the Aza‐Michael Reaction

Rulev

2023

Adv Synth Catal

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The 1,4‐conjugated addition of nitrogen centered nucleophiles to electron‐deficient alkenes is one of the most significant and widely used reactions in modern synthetic organic chemistry. To date, various protocols for the aza‐Michael reaction have been developed. However, these reports mainly focus on the use of strong Michael donors. In recent years, the conjugate addition of weak nitrogen nucleophiles to various Michael acceptors gained increasing popularity. Impressive progress in this area has been achieved by the use of more efficient catalyst systems. This review aims to provide a critical analysis of the results obtained in reactions of weak nucleophiles (azoles, pyrroles, indoles, carbamates, purines, amides, hydrazides, uraciles etc) with electron‐deficient alkenes which were reported over the past twelve years.

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Novel DABCO-Derived Ionic Liquids for Liquid Desiccant Air Conditioning

Lee,

Hong,

Chen

et al. 2024

ACS Sustainable Chem. Eng.

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Conventional air conditioners are inefficient, especially in hot and humid areas, to take water away from the moisture-rich air since this causes higher energy consumption. Liquid desiccant air-conditioning (LDAC) systems represent a promising alternative due to their effective temperature-and humidity-independent control with energy-saving potential. Ionic liquids (ILs) are considered desiccant substitutes for traditional halide salts with better performance and no metal corrosion. This study introduced the synthesis and structure characterization of novel ILs with cations based on 1,4-diazabicyclo[2.2.2]octane (DABCO) and anions derived from trialkylphosphate. The corrosion behavior of copper and aluminum in these IL solutions was studied with an electrochemical test. The resulting ionic liquids were strongly hygroscopic and antimicrobial while showing much lower corrosivity with no risk of crystallization. These advantages made DABCO-derived ILs the potential liquid desiccants of the next generation.

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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

Cited by 6 publications

References 36 publications

DABCO‐Catalysed [3+2] Cyclization/Deformylation Cascade of p‐Quinols with 3‐Formylchromones: Access to Benzopyrone‐Fused Tetracyclic Ring Systems

DABCO‐Catalysed [3+2] Cyclization/Deformylation Cascade of p‐Quinols with 3‐Formylchromones: Access to Benzopyrone‐Fused Tetracyclic Ring Systems

Weak Nucleophiles in the Aza‐Michael Reaction

Novel DABCO-Derived Ionic Liquids for Liquid Desiccant Air Conditioning

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