Mild and selective deprotection of carbamates with Bu4NF

Jacquemard, Ulrich; Bénéteau, Valérie; Lefoix, Myriam; Routier, Sylvain; Mérour, Jean‐Yves; Coudert, G.

doi:10.1016/j.tet.2004.07.071

Cited by 120 publications

(67 citation statements)

References 49 publications

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“…As a result, the desired compound 1-Boc was isolated with satisfactory yield. At the very end it was necessary to remove the Boc group, but all deprotection protocols (HCl in dioxane, [31] TMSOTf, CF 3 COOH with Et 3 -SiH, [32] Bu 4 NF in THF [33] ) failed. Therefore, the same procedure was applied for the direct coupling of substances 9-H and 6-H, without any protection of the amino group.…”

Section: Synthesismentioning

confidence: 99%

Switchable Fluorescent and Solvatochromic Molecular Probes Based on 4‐Amino‐N‐methylphthalimide and a Photochromic Diarylethene

et al. 2008

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New fluorescent photochromic compounds (1-H and 1-Boc) have been synthesized and characterized in different solvents. The fluorescence emission can be switched "on" and "off" with visible light and UV, respectively, by means of the photochromic reaction. The emission wavelength and efficiency strongly depend on the polarity of the solvent. The compounds show a positive solvatochromic effect in the emission maxima, and their fluorescence quantum yield decreases as the solvent's polarity increases (from cyclohexane to dioxane). In solvents more polar than dioxane the emission is too weak and therefore undetectable, and thus 1-H and 1-Boc behave as "normal" photochromic compounds. The pho-

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Section: Synthesismentioning

confidence: 99%

Switchable Fluorescent and Solvatochromic Molecular Probes Based on 4‐Amino‐N‐methylphthalimide and a Photochromic Diarylethene

et al. 2008

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“…The reaction of phenylmagnesium bromide with 10 was also very facile and furnished the pyrimidine derivative 12j in 68% yield. While the deprotection of carbamate from N-3 positions of products 12aej using LiAlH 4 in methanol 17 (stirring at 0 C to room temperature and then reflux), NaOMe in refluxing methanol 33 or tetrabutyl ammonium fluoride (TBAF) in THF 34 could not be achieved, the current methodology served the purpose of appending a variety of substituents at the C-2 position, regioselectively and in a synthetically useful manner. The formation of the products 12 and 15 can be visualized to be proceeding through the mechanism shown in Scheme 2.…”

Section: Resultsmentioning

confidence: 99%

Regioselective addition reactions at C-2 of 3,4-dihydropyrimidinones. Synthesis and evaluation of multifunctionalized tetrahydropyrimidines

2010

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a b s t r a c tMultifunctionalized tetrahydropyrimidines derivatives have been synthesized from Biginelli 3,4-dihydropyrimidin-2-(1H)-thiones (DHPMs) efficiently. The transformation includes desulfurization of DHPMs with Raney-Ni and subsequent regioselective C-2 functionalization using a variety of C-nucleophiles with simultaneous activation with ethyl chloroformate. Functionalized pyrimidine derivatives containing bulky substituents at C-2 of the pyrimidine ring are cytostatic.

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“…), anhydrous THF (30 mL) and TBAF (10.2 mL, 1.0 M in THF, 10.2 mmol, 5.02 eq.) was stirred under argon at reflux for 2 h (Jacquemard et al, 2004). The mixture was allowed to cool before quenching with saturated NH 4 Cl.…”

Section: Methodsmentioning

confidence: 99%

“…For examples of -diketone oxidations using selenium dioxide, see: Gribble et al (1988); Xu et al (2002); Belsey et al (2006). For related cyclopenta [b]indolone alkaloids and their analogues, see: Cheng et al (1991); Garcia-Pichel & Castenholz (1991); Garcia-Pichel et al (1992); Proteau et al (1993); Ekebergh et al (2011); Kobayashi et al (1994); Jacquemard et al (2004); Ploutno & Carmeli (2001). For standard bond lengths, see: Allen et al (1987).…”

Section: Related Literaturementioning

confidence: 99%