2003
DOI: 10.1055/s-2003-41447
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Applications of Lawesson’s Reagent in Organic and Organometallic Syntheses

Abstract: This review, including 245 references, describes the application of Lawesson's reagent [2,4-bis(p-methoxyphenyl)-1,3-dithiaphosphetane-2,4-disulfide] LR in organic and organometallic syntheses. Thionations of carbonyl-containing compounds as well as unexpected reactions are shown for different applications (e.g. cyclizations, rerrangements, syntheses of heterocyclic compounds etc.). Syntheses of novel organometallic compounds by LR are also discussed.

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Cited by 289 publications
(167 citation statements)
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“…The overall results confirm that the steric hindrance provided by the methyl group of DEAdcCE around the -carboxyl ester in combination with HOBt or Oxyma additives during Fmoc-removal represents the best choice to minimize the nucleophilic attack of the amidate anion at the carbonyl group and for instance to reduce aspartimide formation. Taking into account the synthetic problems encountered with DEAdcCM monomer (10) together with its slow photodeprotection rate with green light, we selected DEAdcCE monomer (9) to synthesize the target caged cyclic RGD peptide, c(RGD(DEAdcCE)fK) (18) …”
Section: Synthesis Of a Dicyanocoumarin-caged Cyclic Rgd Peptidementioning
confidence: 99%
See 1 more Smart Citation
“…The overall results confirm that the steric hindrance provided by the methyl group of DEAdcCE around the -carboxyl ester in combination with HOBt or Oxyma additives during Fmoc-removal represents the best choice to minimize the nucleophilic attack of the amidate anion at the carbonyl group and for instance to reduce aspartimide formation. Taking into account the synthetic problems encountered with DEAdcCM monomer (10) together with its slow photodeprotection rate with green light, we selected DEAdcCE monomer (9) to synthesize the target caged cyclic RGD peptide, c(RGD(DEAdcCE)fK) (18) …”
Section: Synthesis Of a Dicyanocoumarin-caged Cyclic Rgd Peptidementioning
confidence: 99%
“…Finally, the photoactivation of the coumarin-caged peptide (18) and its ruthenocene conjugate (20) was studied. As shown in Figure 3, both compounds strongly absorb in the visible region showing a maximum of absorption at  max = 496 nm, which was slightly red-shifted with respect monomer 7 (492 nm).…”
Section: Synthesis and Photochemical Properties Of A Conjugate Betweementioning
confidence: 99%
“…Following the method developed by Pozdnev et al, 22,23 (E)-cinnamic acid 7a was reacted with di-tert-butyl dicarbonate [(Boc)2O], ammonium hydrogen carbonate and pyridine in tetrahydrofuran to afford cinnamamide 8a in good yield (78.5%). Thionation was achieved by stirring cinnamamide 8a with Lawesson's reagent in dry THF at ambient temperature for 8 h, 24 the progress of the reaction being monitored by thin layer chromatography (TLC). Work-up and column chromatography gave (E)-3-phenylprop-2-enethioamide 9a [22][23][24][25][26][27] in 52% yield, with retention of the (E)-configuration about the double bond being confirmed by the large 1 H NMR vinylic coupling constant (J = 15.6 Hz) and conversion of the carbonyl group to thiocarbonyl by the significant downfield shift (= 32 ppm)of the thiocarbonyl (C=S) signal to 198.1 ppm.…”
Section: Resultsmentioning
confidence: 99%
“…Thionation was achieved by stirring cinnamamide 8a with Lawesson's reagent in dry THF at ambient temperature for 8 h, 24 the progress of the reaction being monitored by thin layer chromatography (TLC). Work-up and column chromatography gave (E)-3-phenylprop-2-enethioamide 9a [22][23][24][25][26][27] in 52% yield, with retention of the (E)-configuration about the double bond being confirmed by the large 1 H NMR vinylic coupling constant (J = 15.6 Hz) and conversion of the carbonyl group to thiocarbonyl by the significant downfield shift (= 32 ppm)of the thiocarbonyl (C=S) signal to 198.1 ppm. Application of the conventional Hantzsch method, 13 involving reaction of (E)-3-phenylprop-2-enethioamide 9a with each of the α-halo carbonyl compounds 10a-f (X=Br or Cl) afforded the (E)-2-styrylthiazoles 4a-f. Hydrolysis of the styrythiazole-5-carboxylate ester 4f afforded the corresponding acid 4g as a white solid (65%, method 1).…”
Section: Resultsmentioning
confidence: 99%
“…When of Lawesson's reagent is in solution it can exist in an equilibrium with a more reactive dithiophosphine ylides (1,2) (see Figure 4.5), which exists in two mesomeric forms (1,2). Both these forms can react with the carbonyl group to form the corresponding thione 147 . Hence, it is more likely that, when 2 equivalents of Lawesson's reagent were used, all the carbonyl groups of OddDPP(ThFl) 2 were converted to thiones.…”
Section: Synthesis Of Targetsmentioning
confidence: 99%