1985
DOI: 10.1021/jo00224a015
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Selective sequential demasking of the ester functions of 1-methyl-3,4,5-tris(methoxycarbonyl)pyrazole

Abstract: The adjacent ester functions of l-methyl-3,4,5-tris(methoxycarbonyl)pyrazole can be selectively and sequentially demasked, providing an efficient route to heterogeneous pyrazole triamides. X-ray crystallographic determination of the structure of one of these triamides shows the order of ester hydrolysis to be 5, 4, 3.

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Cited by 22 publications
(18 citation statements)
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“…calcination at 573 K for 4 h) and CuF 2 Á2H 2 O in 20% aqueous HF and subsequent evaporation at room temperature (Davidovich et al, 1972). 3,4,5-Trimethyl-1H-pyrazole (Me 3 pz) was prepared according to the method of Chambers et al (1985). Thermogravimetric/differential thermal analysis mass spectrometry (TG/DTA-MS) was performed on a Netzsch F1 Jupiter device connected to an Aeolos mass spectrometer.…”
Section: Methodsmentioning
confidence: 99%
“…calcination at 573 K for 4 h) and CuF 2 Á2H 2 O in 20% aqueous HF and subsequent evaporation at room temperature (Davidovich et al, 1972). 3,4,5-Trimethyl-1H-pyrazole (Me 3 pz) was prepared according to the method of Chambers et al (1985). Thermogravimetric/differential thermal analysis mass spectrometry (TG/DTA-MS) was performed on a Netzsch F1 Jupiter device connected to an Aeolos mass spectrometer.…”
Section: Methodsmentioning
confidence: 99%
“…Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009 (Lee et al, 1989;Chambers et al,1985). As a result, crystal structures of many pyrazole derivatives have been reported (Xiao et al, 2007Foces-Foces et al, 2006;Qu et al, 2009;.…”
Section: Methodsmentioning
confidence: 99%
“…For the biological activity of pyrazole compounds, see: Chambers et al (1985); Lee et al (1989). For the crystal structures of pyrazole derivatives, see: Foces-Foces et al (2006); Qu (2009) ;Xiao et al (2007Xiao et al ( , 2009 ;.…”
Section: Related Literaturementioning
confidence: 99%
“…Substituted pyrazoles were prepared as reported [23]. 3,4,5-Trimethylpyrazole [26] and 3,5-dimethyl-4-benzyl-pyrazole [27] were synthesized by reported procedures, respectively.…”
Section: Methodsmentioning
confidence: 99%