Metal‐Free Synthesis of Coumarin‐fused Pyrimidines from 4‐Aminocoumarins via Pseudo Four‐component Reaction

Chen, Jing; Ouyang, Chu‐Hao; Xiao, Ting; Hu, Junbo; Li, Jiang‐Sheng

doi:10.1002/slct.201901803

Cited by 17 publications

(3 citation statements)

References 48 publications

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“…Chen and co‐workers reported the synthesis of pyrimidine derivatives 572 via one‐pot pseudo MCR (Scheme 112). [131] The reaction was carried out by reacting 4‐aminocoumarins 107 , two molecules of aromatic aldehydes 1 and ammonium iodidein chlorobenzene (PhCl) at 150 °C in the presence of DMSO. Substrate scope was explored with different substituted 4‐aminocoumarins 107 as well as substituted aromatic aldehydes 1 and the desired product 572 were obtained in moderate to excellent yields.…”

Section: Six‐membered Heterocyclic Compoundsmentioning

confidence: 99%

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

et al. 2023

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Multicomponent reactions (MCRs) have emerged as powerful tools in synthetic chemistry for the efficient synthesis of diverse molecular scaffolds, particularly nitrogen‐containing heterocycles. Despite their numerous advantages, the use of transition metal catalysts or additives in MCRs can present limitations due to cost, toxicity, and environmental concerns. In recent years, there has been a growing interest in transition metal‐free MCRs for the synthesis of N‐heterocyclic compounds. This review provides a comprehensive and concise overview of the recent advancements in transition metal‐free MCRs for the synthesis of valuable N‐heterocycles over the past five years. The review is systematically organized, categorizing the discussed MCRs based on the size of the heterocyclic ring and the number of nitrogen atoms. Only MCRs that result in the formation of heterocyclic rings containing at least one nitrogen atom are included, while the derivatization of N‐heterocycles using transition metal‐free MCRs falls outside the scope of this review. By highlighting the recent developments in this field, this review aims to showcase the potential and significance of transition metal‐free MCRs as sustainable and efficient strategies for accessing N‐heterocyclic compounds. The elimination of transition metals not only simplifies the reaction conditions but also contributes to greener and more environmentally friendly synthetic approaches. This review serves as a valuable resource for researchers interested in the design and application of transition metal‐free MCRs in the synthesis of nitrogen‐containing heterocycles.

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Section: Six‐membered Heterocyclic Compoundsmentioning

confidence: 99%

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

et al. 2023

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“…Coumarin is a significant building block in natural products and organic synthesis, and a large number of efforts have been utilized to explore new synthetic strategies . The use of new catalytic systems for the synthesis of coumarins and the synthesis of new derivatives bearing coumarin building block are two main roads of researches on coumarins .…”

Section: Introductionmentioning

confidence: 99%

Double Brønsted Acidic Media Immobilized on Carbonized Sugarcane Bagasse (CSCB) as a New and Efficient Solid Acid Catalyst for the Synthesis of Coumarins, Dicoumarols and Xanthenes

Rostami

Zare

2019

ChemistrySelect

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This work is the first report on use of carbonized sugarcane bagasse as a carbon bed for a double Brønsted acidic ionic liquid for the synthesis of a new functionalized solid acid catalyst. Immobilization of hydrogen sulfate was performed from the reaction of 3‐amino propyltriethoxysilane with carbonized bagasse and sulfonation of amine groups using sulfuric acid. Thus, ammonium hydrogen sulfate supported sugarcane bagasse (AHS@CSCB) was prepared. The catalyst (AHS@CSCB) was fully characterized by FT‐IR, XRD, TGA, FE‐SEM, elemental‐mapping and EDX techniques. Also, the surface acidity of catalyst was studied by Hammett function. Catalytic properties of the synthesized catalyst were examined in the synthesis of coumarins, dicoumarols and dibenzoxanthenes. All of the products were obtained with high yields in short reaction times and solvent‐free conditions and characterized with 1H and 13CNMR or previously reported products were examined by comparison with reported melting points. Some of the advantages of our method are simple preparation of catalyst and safe handling, very low cost of support and its abundance, high products yield, catalyst recyclability, solvent‐free and easy workup.

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“…These reactions often require harsh reaction conditions and suffer from low selectivities. Multicomponent reactions (MCRs) are exceptionally attractive tools for accomplishing the goal of step and energy economy in the construction of structurally diverse compounds from simple starting materials . In this context, the Yamamoto group reported an elegant Pd/Cu cocatalyzed synthesis of 2-allyl-1,2,3-triazoles via three-component reaction of alkynes, allyl methyl carbonate, and TMSN 3 (Scheme c) .…”

mentioning

confidence: 99%

Copper-Catalyzed Three-Component Reaction of Alkynes, TMSN₃, and Ethers: Regiocontrollable Synthesis of N¹- and N²-Oxyalkylated 1,2,3-Triazoles

et al. 2019

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A new copper-catalyzed selective synthesis of N 1 -and N 2 -oxyalkylated 1,2,3-triazoles has been developed through a three-component reaction of alkynes, TMSN 3 , and ethers. Through this methodology, a series of N 1 -and N 2oxyalkylated 1,2,3-triazoles could be efficiently and regioselectively obtained from simple and readily available starting materials with favorable functional group tolerance.

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Metal‐Free Synthesis of Coumarin‐fused Pyrimidines from 4‐Aminocoumarins via Pseudo Four‐component Reaction

Cited by 17 publications

References 48 publications

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

Double Brønsted Acidic Media Immobilized on Carbonized Sugarcane Bagasse (CSCB) as a New and Efficient Solid Acid Catalyst for the Synthesis of Coumarins, Dicoumarols and Xanthenes

Copper-Catalyzed Three-Component Reaction of Alkynes, TMSN₃, and Ethers: Regiocontrollable Synthesis of N¹- and N²-Oxyalkylated 1,2,3-Triazoles

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Metal‐Free Synthesis of Coumarin‐fused Pyrimidines from 4‐Aminocoumarins via Pseudo Four‐component Reaction

Cited by 17 publications

References 48 publications

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

Double Brønsted Acidic Media Immobilized on Carbonized Sugarcane Bagasse (CSCB) as a New and Efficient Solid Acid Catalyst for the Synthesis of Coumarins, Dicoumarols and Xanthenes

Copper-Catalyzed Three-Component Reaction of Alkynes, TMSN3, and Ethers: Regiocontrollable Synthesis of N1- and N2-Oxyalkylated 1,2,3-Triazoles

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Copper-Catalyzed Three-Component Reaction of Alkynes, TMSN₃, and Ethers: Regiocontrollable Synthesis of N¹- and N²-Oxyalkylated 1,2,3-Triazoles