A simple route to side-chain fluorinated β-lactams from ring-fluorinated aziridines

Konev, Alexander S.; Новиков, Михаил С.; Khlebnikov, Alexander F.; Tehrani, Kourosch Abbaspour

doi:10.1016/j.jfluchem.2006.10.013

Cited by 8 publications

(2 citation statements)

References 37 publications

(45 reference statements)

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“…Evaluation of the synthesized compounds against microorganisms which caused diseases by using photodynamic therapy (PDT) 15 through activated singlet oxygen or reactive oxygen species (ROS). PDT can be applied as an effective cancer treatment due to enhanced permeability and retention (EPR) effect in tumors in comparison with normal tissues and is easily controlled by limiting the area of light irradiation 16,17 .…”

Section: Biocidal Effectsmentioning

confidence: 99%

Synthesis of Fluorine Heterocyclic Nitrogen Systems Derived From Sulfa Drugs as PhotochemicalProbe Agents for Inhibition of Vitiligo Disease-Part II

Abdel‐Rahman¹,

Makki²,

Bawazir³

2010

E-Journal of Chemistry

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Some more new bioactive fluorine heterocyclic systems containing sulfur and nitrogen as six-membered rings such as;N,Nʼ-disubstituted-thiobarbituric acid, 3-thioxo-1,2,4-triazino[5,6-b]indole, 3-sulfanilamido-1,2,4-triazino[5,6-b]indole and 2-trifluoromethyl-4-imino-6-(sulfamido)1,3,5-triazino [3,2-a]indole derivatives (2-13) have been synthetically derived from the interaction of sulfa drugs with fluorine organic compounds (aldehydes, ketones, anhydride) followed by ring closure reactions. Structures of the targets have been established from their elemental and spectral data. Compounds 3, 6, 10 and 13 could be used as photochemical probe agents in compared with nystatin and nalidixic acid for inhibition of vitiligo diseases.

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Section: Biocidal Effectsmentioning

confidence: 99%

Synthesis of Fluorine Heterocyclic Nitrogen Systems Derived From Sulfa Drugs as PhotochemicalProbe Agents for Inhibition of Vitiligo Disease-Part II

Abdel‐Rahman¹,

Makki²,

Bawazir³

2010

E-Journal of Chemistry

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“…According to the first approach, aziridine Ia was subjected to isomerization into α-fluorinated Schiff base VIIIa by the action of SbF 3 as Lewis acid [31,34,45]. Analogous isomerization of aziridine Ib gave Schiff base VIIIb in 94% yield.…”

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confidence: 99%

Monofluorinated aziridines in asymmetric synthesis of chiral fluorinated prop-2-yn-1-amines

et al. 2010

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Nonracemic C-fluoroaziridines were synthesized for the first time by reaction of fluorocarbene with N-diphenylmethylidene-substituted natural amino acid esters. The products were shown to be used in asymmetric synthesis of chiral fluorinated prop-2-yn-1-amines via one-pot process involving isomerization of 2-fluoroaziridines into α-fluoro imines and subsequent reaction with alkynyldifluoroborane generated in situ.Prop-2-yn-1-amines are widely used as medical agents for the treatment of various diseases [1-10] and as building blocks in the synthesis of polyfunctional nitrogen-containing organic compounds [11][12][13][14][15][16][17][18]. Development of convenient synthetic approaches to chiral prop-2-yn-1-amines [19][20][21][22][23][24][25] is an important problem, taking into account that the use of nonracemic drugs is one of the most important lines in modern medicine [26][27][28][29][30].We recently showed that fluorinated prop-2-yn-1-amines can readily be obtained by reaction of potassium arylethynyltrifluoroborates with 3-fluoro-2,2-diphenylaziridine in the presence of boron trifluorideether complex (Scheme 1) [31]. It was found that the formation of fluorinated prop-2-yn-1-amines from monofluoroaziridines involves Lewis acid-catalyzed isomerization of 2-fluoroaziridines into α-fluoro imines which then react with alkynyldifluoroborane. Acceleration of the process and reduction in the amount of by-products in the case of substrates containing a methoxycarbonylmethyl group (R = CH 2 CO 2 Me; A, R 1 = R 2 = H) was rationalized assuming formation of intermediate chelate A [31]. The formation of cyclic intermediate implies that addition of arylethynyl nucleophile at the C=N bond of substrates with a chiral carbon atom (C* in A, R 1 ≠ R 2 ) could occur with high diastereoselectivity due to rigidity of the transition state and proximity of the chiral center to the reaction center [32] (Scheme 1). Therefore, we presumed that the reaction sequence including isomerization of chiral aziridine and subsequent reaction of the imine thus formed with potassium alkynyltrifluoroborate should provide a simple and convenient synthetic route to chiral functionalized prop-2-yn-1-amines. The present article reports on our first results of asymmetric synthesis of fluorinated

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A Simple Route to Side‐Chain Fluorinated β‐Lactams from Ring‐Fluorinated Aziridines.

et al. 2007

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Aziridines. -For synthesis of the target β-lactams (IV), (VII) and (XIII), isomerization of fluoroaziridines (I), (V) and (XI) into fluoroimines is performed using antimony trifluoride as a catalyst. The yields of diphenylketene-derived lactams (VII) are quite low, probably because the Staudinger reaction competes with hydrolysis of imines giving rise to amines which react with the ketenes under formation of amides (VI) and (X). In boiling toluene, dehydrofluorination occurs to furnish lactam (VIII) which is a product of the Staudinger reaction of an intermediary azadiene. -(KONEV, A. S.; NOVIKOV, M. S.; KHLEBNIKOV*, A. F.; TEHRANI, K. A.; J. Fluorine Chem. 128 (2007) 2, 114-119; Fac. Chem., St. Petersburg State Univ., St. Petersburg 198504, Russia; Eng.) -H. Hoennerscheid 20-095

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A simple route to side-chain fluorinated β-lactams from ring-fluorinated aziridines

Cited by 8 publications

References 37 publications

Synthesis of Fluorine Heterocyclic Nitrogen Systems Derived From Sulfa Drugs as PhotochemicalProbe Agents for Inhibition of Vitiligo Disease-Part II

Synthesis of Fluorine Heterocyclic Nitrogen Systems Derived From Sulfa Drugs as PhotochemicalProbe Agents for Inhibition of Vitiligo Disease-Part II

Monofluorinated aziridines in asymmetric synthesis of chiral fluorinated prop-2-yn-1-amines

A Simple Route to Side‐Chain Fluorinated β‐Lactams from Ring‐Fluorinated Aziridines.

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