Synthesis of 4-(trifluoromethyl)pyrrolidines Containing Sulfonyl, Iminosulfonyl, Sulfamide, or Phosphonyl Substituent

Markitanov, Yuriy N.; Тимошенко, Вадим М.; Shermolovich, Yu. G.; Mykhalchuk, Vladimir L.; Grafova, Irina A.; Grafov, Andriy

doi:10.1007/s10593-016-1916-5

Cited by 10 publications

(5 citation statements)

References 9 publications

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“…This methodology was also applied for the synthesis of 4-(trifluoromethyl)pyrrolidines containing iminosulfonyl, sulfonyl, and sulfamide substituents. 138 Rodriguez and co-workers have reported a versatile method to prepare five-or six-membered bisphosphonate rings using tetraethyl vinylidenebisphosphonate (157). 139 Compound 157 has been used as a dipolarophile that reacts with aldehyde 158 and diethyl aminomalonate 159 in THF to afford 4,4bisphosphono pyrrolidines (160) in moderate yields through a Grigg azomethine ylide cyclization (Scheme 30, eq 1).…”

Section: Five-membered Rings: Nonaromatic Aromatic and Benzo-fused He...mentioning

confidence: 99%

“…Timoshenko and co-workers reported a synthesis of the phosphonylated 4-(trifluoromethyl)pyrrolidine 156 through a 1,3-dipolar cycloaddition between the tertiary amine 153 and diethyl 3,3,3-trifluoropropenylphosphonate 154 in the presence of catalytic amounts of TFA and posterior reductive debenzylation (Scheme ). This methodology was also applied for the synthesis of 4-(trifluoromethyl)pyrrolidines containing iminosulfonyl, sulfonyl, and sulfamide substituents …”

Section: Five-membered Rings: Nonaromatic Aromatic and Benzo-fused He...mentioning

confidence: 99%

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Synthetic Methods for Azaheterocyclic Phosphonates and Their Biological Activity: An Update 2004–2024

Mayorquín-Torres,

Simoens,

Bonneure

et al. 2024

Chem. Rev.

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The increasing importance of azaheterocyclic phosphonates in the agrochemical, synthetic, and medicinal field has provoked an intense search in the development of synthetic routes for obtaining novel members of this family of compounds. This updated review covers methodologies established since 2004, focusing on the synthesis of azaheterocyclic phosphonates, of which the phosphonate moiety is directly substituted onto to the azaheterocyclic structure. Emphasizing recent advances, this review classifies newly developed synthetic approaches according to the ring size and providing information on biological activities whenever available. Furthermore, this review summarizes information on various methods for the formation of C–P bonds, examining sustainable approaches such as the Michaelis–Arbuzov reaction, the Michaelis–Becker reaction, the Pudovik reaction, the Hirao coupling, and the Kabachnik–Fields reaction. After analyzing the biological activities and applications of azaheterocyclic phosphonates investigated in recent years, a predominant focus on the evaluation of these compounds as anticancer agents is evident. Furthermore, emerging applications underline the versatility and potential of these compounds, highlighting the need for continued research on synthetic methods to expand this interesting family.

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Section: Five-membered Rings: Nonaromatic Aromatic and Benzo-fused He...mentioning

confidence: 99%

Section: Five-membered Rings: Nonaromatic Aromatic and Benzo-fused He...mentioning

confidence: 99%

Synthetic Methods for Azaheterocyclic Phosphonates and Their Biological Activity: An Update 2004–2024

Mayorquín-Torres,

Simoens,

Bonneure

et al. 2024

Chem. Rev.

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“…Reductive debenzylation of compounds 5 using molecular hydrogen on palladium catalyst provided the respective NH-pyrrolidines. 2 Chemistry of Heterocyclic Compounds 2021, 57 (12), 1149-1154…”

Section: Cycloaddition To Azomethine Ylides Synthesis Of Pyrrolidinesmentioning

confidence: 99%

Synthesis of five-membered heterocycles by [3+2] cycloaddition reactions of sulfur-containing 3,3,3-trifluoropropene derivatives

Markitanov

Тимошенко

2021

Chem Heterocycl Comp

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The present minireview provides a survey of literature reports on the application of 3,3,3-trifluoropropene derivatives bearing sulfurcontaining functional groups at positions 1 or 2 in the synthesis of functionalized five-membered heterocycles -pyrroles, pyrrolines, pyrrolidines, tetrahydrothiophenes, pyrazoles, pyrazolines, pyrazolidines, isoxazoles, isoxazolines, isoxazolidines, and triazoles via [3+2] cycloaddition reactions with 1,3-dipolarophiles.

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“…Obtained in an enantiomerically pure form, phosphonoproline and its analogues [16][17][18][19] were among the first compounds in this series. Surprisingly, the methods for obtaining chiral pyrrolidin-3-ylphosphonic acids, tetrahydropyranylphosphonic acids and their esters have experienced minimal development [20][21][22]. The use of atom-efficient methods of asymmetric catalysis for the synthesis of such compounds is extremely relevant.…”

Section: Introductionmentioning

confidence: 99%

Convenient access to pyrrolidin-3-ylphosphonic acids and tetrahydro-2H-pyran-3-ylphosphonates with multiple contiguous stereocenters from nonracemic adducts of a Ni(II)-catalyzed Michael reaction

Reznikov¹,

Nikerov²,

Sibiryakova³

et al. 2020

Beilstein J. Org. Chem.

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A new synthetic strategy toward nonracemic phosphoryl-substituted pyrrolidines and tetrahydropyranes with three and five contiguous stereocenters is presented. Readily available β-keto phosphonates react with conjugated nitroolefins in the presence of a chiral Ni(II) complex to give nitro keto phosphonates with two stereocenters with excellent enantioselectivity and moderate to high diastereoselectivity. These products were used for a reductive cyclization leading to pyrrolidin-3-ylphosphonic acid and for reactions with aldehydes yielding tetrahydropyranylphosphonates as individual stereoisomers. These nonracemic heterocycles containing phosphoryl moieties are useful for designing new pharmacologically active compounds.

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Synthesis of 4-(trifluoromethyl)pyrrolidines Containing Sulfonyl, Iminosulfonyl, Sulfamide, or Phosphonyl Substituent

Cited by 10 publications

References 9 publications

Synthetic Methods for Azaheterocyclic Phosphonates and Their Biological Activity: An Update 2004–2024

Synthetic Methods for Azaheterocyclic Phosphonates and Their Biological Activity: An Update 2004–2024

Synthesis of five-membered heterocycles by [3+2] cycloaddition reactions of sulfur-containing 3,3,3-trifluoropropene derivatives

Convenient access to pyrrolidin-3-ylphosphonic acids and tetrahydro-2H-pyran-3-ylphosphonates with multiple contiguous stereocenters from nonracemic adducts of a Ni(II)-catalyzed Michael reaction

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