The sulfide group as an aldehyde precursor

Bakuzis, Peter; BAKUZIS, M. L. F.; Fortes, C. C.; Santos, Raquel Sánchez

doi:10.1021/jo00878a027

Cited by 48 publications

(28 citation statements)

References 2 publications

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“…Thus, when 1 was reacted with one equivalent of ethanedithiol in the presence of four equivalents of triethylamine the major product was 2-cyanomethyl-1,3-dithiolane 21 (77%). 11 The minor product of this reaction was the dimeric thioenol ether 22. Similar results were obtained when propane-1,3-dithiol was employed as nucleophile, yielding 2-cyanomethyl-1,3-dithiane 23 (53%), together with lesser amounts of the bis-thioether 24.…”

Section: Resultsmentioning

confidence: 99%

Addition of nucleophiles to (E)-3-phenylsulfonylprop-2-enenitrile: a route to β-substituted α,β-unsaturated nitriles and to acetals of cyanoacetaldehyde

Grayson¹,

O’Donnell²

2002

Arkivoc

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Section: Resultsmentioning

confidence: 99%

Addition of nucleophiles to (E)-3-phenylsulfonylprop-2-enenitrile: a route to β-substituted α,β-unsaturated nitriles and to acetals of cyanoacetaldehyde

Grayson¹,

O’Donnell²

2002

Arkivoc

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“…The diethylamine derivatives 10 t o 12 and 14 t o 17 (Scheme 3) derive from the corresponding bromides: 1-bromo-3-phenoxypropane and 1-bromo-4-phenoxybutane were commercially available; 1-bromo-3-phenylthiopropane [29] , 1-bromo-4-phenylthiobutane [29] , 1-bromo-5-phenoxypentane [30] , 1-bromo-6-phenoxyhexane [31] were synthesised according to the published methods. 1-Bromo-5-phenylthiopentane was prepared in a similar way to its lower homologues rather than as published [32] .…”

Section: Chemical Synthesismentioning

confidence: 99%

“…Prepared according to general method B from 1-bromo-4-phenylthiobutane [29] .-1 H NMR (D2O) δ = 7.27 (m, 5H), 3.01 (t, 7.3 Hz, 2H), 2.91 (m, 3×2H), 1.59 (m, 2×2H), 1.04 (t, 7.3 Hz, 2×3H). [32] A mixture of thiophenol (1.82 g, 16.6 mmol), 1,5-dibromopentane (9.28 g, 40.4 mmol), sodium hydroxide ( 1.05 g, 26.3 mmol), water (50 mL), toluene (50 mL) and a 40% aqueous solution of tetrabutylammonium hydroxide (1 mL) was stirred at room temperature under nitrogen for 25 min.…”

Section: Nn-diethyl(4-phenylthiobutyl)amine Oxalate (11)mentioning

confidence: 99%

Synthesis of Potent Non-imidazole Histamine H3-Receptor Antagonists

Ganellin¹,

Leurquin

Piripitsi

et al. 1998

Arch. Pharm. Pharm. Med. Chem.

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Histamine has been converted into a non‐imidazole H3‐receptor histamine antagonist by addition of a 4‐phenylbutyl group at the Nα‐position followed by removal of the imidazole ring. The resulting compound, N‐ethyl‐N‐(4‐phenylbutyl)amine, remarkably has a Ki = 1.3 μM as an H3 antagonist. Using this as a lead compound, a novel series of homologous O and S isosteric tertiary amines was synthesised and structure‐activity studies furnished N‐(5‐phenoxypentyl)pyrrolidine (Ki = 0.18 ± 0.10 μM, for [3H]histamine release from rat cerebral cortex synaptosomes) which, more importantly, was active in vivo. Substitution of NO2 into the para position of the phenoxy group gave N‐(5‐p‐nitrophenoxypentyl)pyrrolidine, UCL 1972 (Ki = 39 ± 11 nM), ED50 = 1.1 ± 0.6 mg/kg per os in mice on brain tele‐methylhistamine levels.

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“…Migration of the chloro group of the resulting intermediates 6 would afford a-chlorosulfides 7, poised for dehydrochlorination to oxidized specis 4 [eq. (3)].…”

mentioning

confidence: 99%

“…In this note, we report the successful application of eqs. (2) and (3) to the synthesis of 4 and the adaptation of eq. (3) to the preparation of a thermally crosslinkable polyimidosulfide.…”

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confidence: 99%

Synthesis of a new thermally‐curable elastomer via regioselective chlorination of a polyimidosulfide

White

1987

J. Polym. Sci. A Polym. Chem.

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Recently, we exploited the well established nucleophilic addition of dithiols to bismaleimides' to prepare a sena of high molecular-weight, elastomeric polyimidosullides (Tg = 6.5-13"C), such as 1, via polymerizations of various alkanedithiols with N,N'-bismaleimido-1,8-octane [eq. (1)12 1An an ap roach to the rational introduction of unsaturated curin sites in polymers like 1 under mild conflitions, we studied oxidative conversions of 3-thi~l-~~~y1-2,5-pyrrolidinediones (21, prepared from N-phenylmaleimide (3) via eq. 2), to the corresponding 3-thio-1-phenyl-1H-pyrrole-2,5-diones (4) through chlorination of 2 w i 6 N-chlorosuccinimide (NCS):c, R = 4-ClPhCH2-Extrapolating from the known regioselective chlorination of unsymmetrical benzylic sulfides with NCS? one can view analogous reactions of 2 as initial formation of chlorosulfonium salts 6 [eq. (3)] with subsequent abstraction, by succinimidyl anion (from NCS), of the acidic ring methine proton a to sulfur.

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The sulfide group as an aldehyde precursor

Cited by 48 publications

References 2 publications

Addition of nucleophiles to (E)-3-phenylsulfonylprop-2-enenitrile: a route to β-substituted α,β-unsaturated nitriles and to acetals of cyanoacetaldehyde

Addition of nucleophiles to (E)-3-phenylsulfonylprop-2-enenitrile: a route to β-substituted α,β-unsaturated nitriles and to acetals of cyanoacetaldehyde

Synthesis of Potent Non-imidazole Histamine H3-Receptor Antagonists

Synthesis of a new thermally‐curable elastomer via regioselective chlorination of a polyimidosulfide

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