Seven‐Membered and Larger Ring‐Fluorinated Heterocycles

Петров, В. А.

doi:10.1002/9780470528952.ch10

Cited by 3 publications

(2 citation statements)

References 73 publications

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“…Nitrogen (N)‐containing heterocyclic compounds are more common in nature than the other heterocyclic ring systems [1–4] . Fluorinated N ‐heterocycles, a subclass of N ‐heterocycles, historically traced back to the synthesis of 2‐fluoropyridine by Chichibabine in 1915, however extensive research towards their synthesis did not begin until World War II [5,6] . The C−F bond is one of the strongest (115.7 kcal/mol) and most polar (dipole moment 1.41 D) bond [7] .…”

Section: Introductionmentioning

confidence: 99%

Microwave‐Assisted Synthesis of Fluorinated 5‐Membered Nitrogen Heterocycles

Prakash,

Singh

2024

ChemistrySelect

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The fluorinated 5‐membered N‐containing heterocyclic compounds have wide utility in varied fields. The importance of these compounds has encouraged researchers to explore environment‐friendly synthetic techniques for their synthesis. In this context, microwave‐assisted synthesis has proved beneficial for the synthesis of fluorinated 5‐membered N‐heterocycles in an environmentally benign and energy‐efficient manner. Compared to conventional heating, it offers several advantages, including quick heating, short reaction times, higher yields, and fewer side reactions. This article highlights the microwave‐assisted fluorination of 5‐membered N‐heterocyclic compounds along with the synthesis of fluorinated 5‐membered N‐heterocyclic compounds using fluorinated starting materials.

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Section: Introductionmentioning

confidence: 99%

Microwave‐Assisted Synthesis of Fluorinated 5‐Membered Nitrogen Heterocycles

Prakash,

Singh

2024

ChemistrySelect

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“…Fluorine is widely considered as an important element in pharmaceutical and agrochemical industry. 1,2 Fluorination can have a significant effect on a compound's potency, lipophilicity, pK a , as well as membrane permeability. [3][4][5][6][7][8][9][10] The introduction of a difluoromethyl group onto aromatic and heterocyclic rings has received less attention than trifluoromethylation, perhaps due to scarce available synthetic methods.…”

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confidence: 99%

Facile In Situ Difluoromethylation of Phenols and Thiols Using Ethyl Bromodifluoroacetate and K2CO3

Dond,

Chavan,

Thore

2024

Synlett

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Herein, we report an efficient method to access difluoromethyl ethers of thiols and phenols using ethyl bromodifluoroacetate and K2CO3. This method demonstrates chemoselective difluoromethylation of thiols and phenols in the presence of amines. The current method also discloses the synthesis of bis(aryloxy)fluoromethane compounds which are least reported in the literature. Mechanistic investigations revealed that the reaction proceeds through a nucleophilic substitution pathway. We strongly believe this protocol would offer an efficient alternative to earlier photocatalyzed or radical-mediated difluoromethylation methods and it has a great potential in the scale-up of pharmaceutical and agrochemical intermediates that possess difluoromethyl group.

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Regioselective Synthesis of 4,5‐Dihydro‐6H‐oxepino[3,2‐c]chromene‐2,6(3H)‐diones through Palladium‐Catalyzed Intramolecular Alkoxycarbonylation of 3‐Allyl‐4‐hydroxycoumarins

2019

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Seven‐membered ring lactones fused to coumarin scaffolds were obtained via a palladium‐catalyzed regioselective intramolecular alkoxycarbonylation under a CO atmosphere. Cyclocarbonylation of 3‐allyl‐4‐hydroxycoumarin derivatives was accessed in the absence of hydrogen gas, acidic conditions, or any other additives. The results of the control experiments revealed the importance of pKa of the substrate for initiating the reaction.

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Seven‐Membered and Larger Ring‐Fluorinated Heterocycles

Cited by 3 publications

References 73 publications

Microwave‐Assisted Synthesis of Fluorinated 5‐Membered Nitrogen Heterocycles

Microwave‐Assisted Synthesis of Fluorinated 5‐Membered Nitrogen Heterocycles

Facile In Situ Difluoromethylation of Phenols and Thiols Using Ethyl Bromodifluoroacetate and K2CO3

Regioselective Synthesis of 4,5‐Dihydro‐6H‐oxepino[3,2‐c]chromene‐2,6(3H)‐diones through Palladium‐Catalyzed Intramolecular Alkoxycarbonylation of 3‐Allyl‐4‐hydroxycoumarins

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