Facile preparation of N-(sulfonyl)carbamates

Neustadt, Bernard R.

doi:10.1016/0040-4039(94)85058-5

Cited by 71 publications

(54 citation statements)

References 5 publications

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“…Firstly, two macrocycles 3 a and 4 containing the same arylic unit, p-tolylsulfonamide, were prepared. The whole synthesis started with the reaction of N-tert-butyloxycarbonyl (Boc)-protected p-tolylsulfonamide 5 [28] and 0.5 equiv of 2-butyne-1,4-diol under Mitsunobu reaction conditions to give compound 6. The elimination of the Boc groups in compound 6 (to give 7) and the subsequent treatment with two equivalents of bromo derivative 8 [5] resulted in the isolation of compound 9 with an 80 % yield.…”

Section: Resultsmentioning

confidence: 99%

Rhodium(I)‐Catalysed Intramolecular [2+2+2] Cyclotrimerisations of 15‐, 20‐ and 25‐Membered Azamacrocycles: Experimental and Theoretical Mechanistic Studies

Dachs¹,

Torrent²,

Roglans³

et al. 2009

Chemistry A European J

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A new series of 20- and 25-membered polyacetylenic azamacrocycles have been satisfactorily prepared and completely characterised by spectroscopic methods. Various [2+2+2] cyclotrimerisation processes catalysed by the Wilkinson's catalyst, [RhCl(PPh(3))(3)], were tested in the above-mentioned macrocycles. The 25-membered azamacrocycle (like the previously synthesised 15-membered azamacrocyle) led to the expected cyclotrimerised compound in contrast to the 20-membered macrocycle, which is characterised by its lack of reactivity. The difference in reactivity of the 15-, 20- and 25-membered macrocycles has been rationalised through density functional theory calculations.

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Section: Resultsmentioning

confidence: 99%

Rhodium(I)‐Catalysed Intramolecular [2+2+2] Cyclotrimerisations of 15‐, 20‐ and 25‐Membered Azamacrocycles: Experimental and Theoretical Mechanistic Studies

Dachs¹,

Torrent²,

Roglans³

et al. 2009

Chemistry A European J

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“…As shown in Scheme 1, five side chains 5a-e were synthesized in three steps. After amine protection with (Boc) 2 O in 2a [16], the hydroxyl group in 2-aminoethanol 3a was transformed into an 2-alkoxylamine through Mitsunobu reaction and the subsequent hydrazine reduction [17]. Using the same method, the five alkoxylamine analogues 5a-e were prepared (Scheme 1).…”

Section: Synthesis Of the Alkoxylamine Analog Conjugates 9a-gmentioning

confidence: 99%

Synthesis and Biological Evaluation of RGD-Conjugated MEK1/2 Kinase Inhibitors for Integrin-Targeted Cancer Therapy

Hou

Wang

et al. 2013

Molecules

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Two novel series of RGD-MEKI conjugates derived from a MEK1/2 kinase inhibitor-PD0325901-have been developed for integrin receptor mediated anticancer therapy. The first series, alkoxylamine analog RGD-MEKI conjugates 9a-g showed anti-proliferation activity in melanoma A375 cells by the same mechanism as that of PD0325901. PEGylation increased the IC 50 value of 9f three-fold in the A375 assay, and the multi-cRGD peptide cargo significantly improved the receptor specific anti-proliferation activity of 9g in integrin-overexpressing U87 cells. In the second series, RGD-PD0325901 13 exhibited significantly increased antitumor properties compared to the alkoxylamine analogs by both inhibition of the ERK pathway activity and DNA replication of the cancer cells. Furthermore, 13 displayed more potent anti-proliferation activity in the U87 assay than PD0325901 in a dose-dependent manner. All these data demonstrate that RGD-MEKI conjugates with an ester bond linkage enhanced anticancer efficacy with improved targeting capability toward integrin-overexpressing tumor cells.

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“…aq. N-Boc-Sulfonamide 51: Triphenylphosphine (1.147 g, 4.37 mmol), 4-penten-1-ol (0.45 mL, 4.37 mmol), and N-Boc-4-nitrobenzenesulfonamide 50 [11] (1.320 g, 4.37 mmol) were dissolved in THF (30 mL). Then diisopropyl azodicarboxylate (0.86 mL, 4.37 mmol) was added to the solution over 20 minutes and reaction was allowed to stir at room temperature overnight.…”

Section: N-boc-tosylsulfonamide 35mentioning

confidence: 99%

Gold‐Catalyzed Intramolecular Aminoarylation of Alkenes: CC Bond Formation through Bimolecular Reductive Elimination

et al. 2010

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Facile preparation of N-(sulfonyl)carbamates

Cited by 71 publications

References 5 publications

Rhodium(I)‐Catalysed Intramolecular [2+2+2] Cyclotrimerisations of 15‐, 20‐ and 25‐Membered Azamacrocycles: Experimental and Theoretical Mechanistic Studies

Rhodium(I)‐Catalysed Intramolecular [2+2+2] Cyclotrimerisations of 15‐, 20‐ and 25‐Membered Azamacrocycles: Experimental and Theoretical Mechanistic Studies

Synthesis and Biological Evaluation of RGD-Conjugated MEK1/2 Kinase Inhibitors for Integrin-Targeted Cancer Therapy

Gold‐Catalyzed Intramolecular Aminoarylation of Alkenes: CC Bond Formation through Bimolecular Reductive Elimination

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