Copper-Catalyzed Synthesis of Coumarins. A Mini-Review

Novel, substituted chromenopyrrolidininones have been synthesized from natural amino acid derivatives through an unprecedented sequence involving a Knoevenagel-transesterification sequence and an allylative palladium-catalyzed cyclization reaction. The products are nature-inspired heterocycles derived from natural amino acids. The targets could be synthesized with varying degrees of stereoselectivity: racemization is a known issue with amino acids and provided a formidable challenge to our method development, as well. Altogether, six derivatives were synthesized with yields from moderate to good.

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“…A recent review by Dalpozzo et al highlights recent advances in the asymmetric synthesis of chromene derivatives. 4…”

Section: Table 1 Control Experiments To Investigate Rac...mentioning

confidence: 99%

Diastereoselective Synthesis of Substituted Chromenopyrrolidinones from Amino Acid Derived Nitriles

Heikinheimo

Nieger

Koskinen

2022

Synlett

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“…42,43 In the last decade, the PKR has been effectively applied in the total synthesis of natural products having 5,5-, 5,6-, and 5,7-bicyclic ring systems. 44,45 In this regard, our group reported a series of Co 2 (CO) 8 -mediated PKR for the formation of fluorinated enantioenriched nitrogen-containing bicycles (Figure 1). 46,47 More interestingly, the intramolecular PKR of enynes containing a vinyl fluoride moiety was successfully developed by using appropriate reaction conditions without obtaining adducts from HF elimination.…”

Section: Paper Synthesismentioning

confidence: 99%

A Density Functional Theory Study on the Cobalt-Mediated Intramolecular Pauson–Khand Reaction of Enynes Containing a Vinyl Fluoride Moiety

Escorihuela¹

2022

Synthesis

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The Co2(CO)8-mediated intramolecular Pauson–Khand reaction (PKR) is an effective method for constructing polycyclic structures. Recently, our group reported a series of this type of reaction involving fluorinated enynes that proceed with reasonable reaction rates and yields. However, mechanistic studies involving these fluorinated derivatives in intramolecular PKR are scarce. In this study, density functional theory calculations are used to clarify the mechanism and reactivity of enynes containing a vinyl fluoride moiety for this reaction. In agreement with previous studies, alkene insertion is considered to be the rate-determining step for the overall Pauson–Khand reaction of enynes containing a vinyl fluoride moiety. The effect of the substituent on the Co2(CO)8-mediated intramolecular Pauson–Khand reaction has also been investigated. When introducing heteroatoms as tethering units, the fluorinated enynes exhibited lower reactivity than the malonate homologues, whereas the use of a sulfur-based tether was unsuccessful. This computational study provides detailed information about the PKR mechanism and transition-state structures, and the results are validated with previous experimental results.

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“…3,9-Dihydroxyazacoumestan (I) is an angiogenesis inhibitor [ 50 ], while 1-aryl-3-phenylpyrrolo[3,2-c]coumarins II are benzodiazepine receptor ligands [ 48 , 49 ]. In the literature, many reviews have been published concerning the synthesis and biological activities of coumarin and fused coumarin derivatives, while fused pyrrolocoumarins have appeared in some reviews [ 1 , 14 , 45 , 60 , 61 , 62 , 63 , 64 , 65 , 66 , 67 ] and in a few specific reviews [ 57 , 58 , 68 ]. This review will present an overview of the synthesis and biological evaluation of fused pyrrolo[ c ]coumarins.…”

Section: Introductionmentioning

confidence: 99%

“…Molecules 2024, 29, 2748 2 of 62 derivatives, while fused pyrrolocoumarins have appeared in some reviews [1,14,45,[60][61][62][63][64][65][66][67] and in a few specific reviews [57,58,68]. This review will present an overview of the synthesis and biological evaluation of fused pyrrolo[c]coumarins.…”

Section: Introductionmentioning

confidence: 99%

An Overview of the Synthesis of 3,4-Fused Pyrrolocoumarins of Biological Interest

Kapidou,

Litinas

2024

Molecules

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3,4-Fused pyrrolocoumarins, synthetically prepared or naturally occurring, possess interesting biological properties. In this review, the synthetic strategies for the synthesis of the title compounds are presented along with their biological activities. Two routes are followed for that synthesis. In one, the pyrrole ring is formed from coumarin derivatives, such as aminocoumarins or other coumarins. In the other approach, the pyranone moiety is built from an existing pyrrole derivative or through the simultaneous formation of coumarin and pyrrole frameworks. The above syntheses are achieved via 1,3-dipolar cycloaddition reactions, Michael reaction, aza-Claisen rearrangement reactions, multi-component reactions (MCR), as well as metal-catalyzed reactions. Pyrrolocoumarins present cytotoxic, antifungal, antibacterial, α-glucosidase inhibition, antioxidant, lipoxygenase (LOX) inhibition, and fluorescent activities, as well as benzodiazepine receptor ability.

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Copper-Catalyzed Synthesis of Coumarins. A Mini-Review

Cited by 7 publications

References 58 publications

Diastereoselective Synthesis of Substituted Chromenopyrrolidinones from Amino Acid Derived Nitriles

Diastereoselective Synthesis of Substituted Chromenopyrrolidinones from Amino Acid Derived Nitriles

A Density Functional Theory Study on the Cobalt-Mediated Intramolecular Pauson–Khand Reaction of Enynes Containing a Vinyl Fluoride Moiety

An Overview of the Synthesis of 3,4-Fused Pyrrolocoumarins of Biological Interest

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