All melting points were taken on a hot stage apparatus (Electrothermal, Essex, UK) and were reported uncorrected. IR spectra were recorded with a Perkin-Elmer spectrometer (KBr disk) (PerkinElmer, Waltham, MA, USA). NMR spectra were recorded on a Bruker Avance 300 spectrometer (300 MHz for 1H NMR, 75 MHz for 13C NMR). Mass spectra were obtained with an Agilent spectrometer (9575c inert MSD; Agilent Technologies, Santa Clara, CA, USA). Chromatographic separations were performed on a silica gel column by gravity chromatography (Kieselgel 40, 0.063–0.200 mm; Merck) or flash chromatography (Kieselgel 40, 0.040–0.063 mm; Merck). Yields are given after purification, unless otherwise stated. All compounds were named following IUPAC guidelines as defined by ChemBioDraw Ultra 12.0 software.
Kieselgel 40
Manufactured by Merck Group
Sourced in United States
Kieselgel 40 is a high-purity silica gel product used in various laboratory applications. It is a fine, porous material with a high surface area, making it suitable for chromatographic separations, adsorption, and desiccation processes.
Automatically generated - may contain errors
Lab products found in correlation
Sy spectrometer, by Agilent Technologies (3 mentions)
Mercury as400, by Agilent Technologies (3 mentions)
Smp 20, by Büchi (3 mentions)
Avance 3 hd 400 mhz spectrometer, by Bruker (3 mentions)
Silica gel 60 f254, by Merck Group (2 mentions)
Wp 200 sy spectrometer, by Bruker (2 mentions)
Sy spectrometer, by Bruker (2 mentions)
5890 series 2 mass detector, by Hewlett-Packard (2 mentions)
Mercury 400 100 mhz spectrometer, by Agilent Technologies (2 mentions)
Flash 2000, by Thermo Fisher Scientific (2 mentions)
Isolute flash si 2 cartridges, by Biotage (2 mentions)
Mercury spectrometer, by Agilent Technologies (1 mentions)
Eclipse plus c18 column, by Agilent Technologies (1 mentions)
Avance 2 500 spectrometer, by Bruker (1 mentions)
Microtof q 2, by Bruker (1 mentions)
Mercury 400 100 mhz, by Agilent Technologies (1 mentions)
Ac 200 spectrometer, by Bruker (1 mentions)
Avance 3 400 mhz spectrometer, by Bruker (1 mentions)
Kbr disk, by PerkinElmer (1 mentions)
Avance 400 spectrometer, by Brucker (1 mentions)
23 protocols using kieselgel 40
1
Synthesis and Characterization of Organic Compounds
2
Analytical Protocols for Compound Characterization
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All melting points were taken on a Büchi apparatus and are uncorrected. NMR spectra were recorded on a Brucker Avance 400 spectrometer (400 MHz for 1H NMR, 100 MHz for 13 C). Chromatographic separations were performed on a silica gel column by gravity chromatography (Kieselgel 40, 0.063–0.200 mm; Merck) or flash chromatography (Kieselgel 40, 0.040–0.063 mm; Merck). Yields are given after purification, unless differently stated. When reactions were performed under anhydrous conditions, the mixtures were maintained under nitrogen. High-resolution mass spectrometry (HR-MS) analyses were performed with a Thermo Finnigan LTQ Orbitrap mass spectrometer equipped with an electrospray ionisation source (ESI). Analyses were carried out in positive ion mode monitoring protonated molecules, [M + H]+ species, and a proper dwell time acquisition was used to achieve 60,000 units of resolution at Full Width at Half Maximum (FWHM). Elemental composition of compounds were calculated on the basis of their measured accurate masses, accepting only results with an attribution error less than 5 ppm and a not integer RDB (double bond/ring equivalents) value, in order to consider only the protonated species22 . Compounds were named following IUPAC rules by means of ChemDraw 14.0.
3
Synthesis and Characterization of Heterocyclic Compounds
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All melting points were taken on a Büchi apparatus and are uncorrected. Infrared spectra were recorded with a Perkin-Elmer Spectrum RX I FT-IR spectrophotometer in Nujol mull for solids and neat for liquids. NMR spectra were recorded on a Bruker Avance 400 spectrometer (400 MHz for 1 H NMR, 100 MHz for 13 C NMR) using residual solvent such as chloroform (δ = 7.26) as internal standard. Chromatographic separations were performed on a silica gel column by gravity chromatography (Kieselgel 40, 0.063-0.200 mm; Merck) or flash chromatography (Kieselgel 40, 0.040-0.063 mm; Merck). Yields are given after purification, unless otherwise stated. When reactions were performed in anhydrous conditions, the mixtures were maintained under nitrogen.
The combustion analyses of compounds 1-13 are indicated by symbols, and the analytical results are within 0.4% of the theoretical values. ESI-MS spectra were obtained using a Varian 1200L triple quadrupole system (Palo Alto, CA, USA) equipped by Elettrospray Source (ESI) operating in both positive and negative ions. Except for compounds 3 and 4, the free bases form of the final compounds were transformed into the dihydrochloride by treatment with 2.2 eq of acetyl chloride in anhydrous CH 3 OH. The salts were crystallized from abs. ethanol/petroleum ether. Compounds were named following IUPAC rules as applied by ChemBioDraw Ultra 14.0 software.
The combustion analyses of compounds 1-13 are indicated by symbols, and the analytical results are within 0.4% of the theoretical values. ESI-MS spectra were obtained using a Varian 1200L triple quadrupole system (Palo Alto, CA, USA) equipped by Elettrospray Source (ESI) operating in both positive and negative ions. Except for compounds 3 and 4, the free bases form of the final compounds were transformed into the dihydrochloride by treatment with 2.2 eq of acetyl chloride in anhydrous CH 3 OH. The salts were crystallized from abs. ethanol/petroleum ether. Compounds were named following IUPAC rules as applied by ChemBioDraw Ultra 14.0 software.
4
Analytical Techniques for Organic Synthesis
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Analytical grade reagents
and solvent were
purchased from Sigma-Aldrich (St. Louis, MO) and were used as supplied.
Solvents were dried according to standard methods. Melting points
were determined on a Köfler hot-stage apparatus and are uncorrected. 1H NMR spectra were recorded with a Varian Gemini-200 MHz spectrometer
in an ca. 2% solution of CDCl3. Chemical shifts (δ)
are reported in parts per million (ppm) downfield from tetramethylsilane
(TMS) as internal standard. The following abbreviations are used:
singlet (s), broad (br), and multiplet (m). Reactions were monitored
by thin layer chromatography (TLC) on silica gel plates containing
a fluorescent indicator (Merck Silica Gel 60 F254), and spots were
detected under UV light (254 nm). Chromatographic separations were
performed on silica gel columns by flash column chromatography (Kieselgel
40, 0.040–0.063 mm; Merck). Na2SO4 was
always used as the drying agent. Evaporation was carried out “in
vacuo” (rotating evaporator). Elemental analyses were performed
by our analytical laboratory and agreed with the theoretical values
to within ±0.4%.
and solvent were
purchased from Sigma-Aldrich (St. Louis, MO) and were used as supplied.
Solvents were dried according to standard methods. Melting points
were determined on a Köfler hot-stage apparatus and are uncorrected. 1H NMR spectra were recorded with a Varian Gemini-200 MHz spectrometer
in an ca. 2% solution of CDCl3. Chemical shifts (δ)
are reported in parts per million (ppm) downfield from tetramethylsilane
(TMS) as internal standard. The following abbreviations are used:
singlet (s), broad (br), and multiplet (m). Reactions were monitored
by thin layer chromatography (TLC) on silica gel plates containing
a fluorescent indicator (Merck Silica Gel 60 F254), and spots were
detected under UV light (254 nm). Chromatographic separations were
performed on silica gel columns by flash column chromatography (Kieselgel
40, 0.040–0.063 mm; Merck). Na2SO4 was
always used as the drying agent. Evaporation was carried out “in
vacuo” (rotating evaporator). Elemental analyses were performed
by our analytical laboratory and agreed with the theoretical values
to within ±0.4%.
5
Purification and Characterization of Organic Compounds
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Reagents were used as purchased without further purification. Solvents for synthesis (dichloromethane and acetonitrile) were dried and freshly distilled before use according to procedures described in the literature. TLC was performed on pre-coated silica gel polyester plates (0.25 mm thickness) with a UV fluorescence indicator 254 (Polychrome SI F254). Chromatographic purification was performed on silica gel columns by flash (Kieselgel 40, 0.040–0.063; Merck) chromatography. Melting point was determined on a Büchi 510. 1H NMR and 13C NMR spectra were recorded in CDCl3 or DMSO‑d6 on a Varian Mercury spectrometer operating at 400/100 MHz. Chemical shifts (δ) are given in ppm downfield from tetramethylsilane and coupling constants (J values) are in Hertz. IR spectra were run on a Nicolet Impact 410 Spectrophotometer. For FAB-HRMS analyses, a VG-TS250 apparatus (70 eV) was used.
6
Analytical Methods for Compound Characterization
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All reagents were obtained at highest quality from commercially available sources and were used as received. All compounds were elucidated by NMR and HRMS data. Anal. TLC: aluminum plates precoated with Merck Silica gel 60 F254 as an adsorbent; visualization on TLC plates was done with UV light. Column chromatography (CC): silica gel (SiO2; Kieselgel 40, 0.063–0.200 mm, Merck). HPLC: Agilent 1100 series coupled to IR/UV/VIS detector; a ZORBAX Eclipse Plus C18 column (particle size 5 μm, 250 × 4.6 mm i.d.); the mobile phase, MeOH/H2O/CH3COOH; flow rate, 0.5–1 mL min−1; the chromatograms monitored at 260 nm. Ultrasonic bath: Branson 1210E-MT ultrasonic bath, operating at 47 kHz. NMR Spectra: NMR Bruker Avance II 500 spectrometer (at 500 and 125 MHz for 1H and 13C, resp.), at 25 °C; δ in ppm, J in Hz; HR-ESI–MS: Bruker Daltonics micrOTOF-QII; in m/z.
7
Characterization of Organic Compounds
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Reagents were used as purchased without further purification. Solvents (THF, DMF, CH2Cl2) were dried and freshly distilled before use according to procedures reported in the literature. Chromatographic separations were performed on silica gel columns by flash (Kieselgel 40, 0.040–0.063; Merck). TLC was performed on precoated silica gel polyester plates (0.25 mm thickness, with UV 254 fluorescent indicator). Melting points were determined on a Buchi 510 apparatus and are uncorrected. 1H NMR and 13C NMR spectra were recorded on a Bruker AC200 spectrometer at 200/50 MHz, on a Bruker SY spectrometer at 400/100 MHz or on a Varian Mercury 400/100 MHz, using CDCl3 as solvent (unless otherwise stated). Chemical shifts (δ) are given in ppm downfield from tetramethylsilane, and coupling constants (J values) are in Hertz. Electrospray-ionisation (ESI) high-resolution mass spectra (HRMS) were obtained on a VG-TS250 apparatus (70 eV). A Helios Alfa UV-320 from Thermo-Spectronic was used for UV spectra and turbidimetric measurements. IR spectra were acquired in a FTIR Nicolet Impact 410 equipment (film, unless otherwise stated) and the absorptions are expressed in cm−1. The aqueous solubility of the compound was determined in a Helios Alfa Spectrophotometer.
8
Comprehensive Characterization of Organic Compounds
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Reagents were used as purchased without further purification. Solvents (EtOAc, DMF, CH2Cl2, toluene, MeOH and CH3CN) were stored over molecular sieves. THF was refluxed with sodium/benzophenone and hexane was dried by distillation and stored over CaCl2. TLC was performed on precoated silica gel polyester plates (0.25 mm thickness) with a UV fluorescence indicator 254 (Polychrom SI F254). Chromatographic separations were performed on silica gel columns by flash (Kieselgel 40, 0.040–0.063; Merck) chromatography. Melting points were determined on a Buchi 510 apparatus and are uncorrected. 1H NMR and 13C NMR spectra were recorded in CDCl3, CD3OD, DMSO-D6 or Acetone-D6 on a Bruker WP 200-SY spectrometer at 200/50 MHz or a Bruker SY spectrometer at 400/100 MHz. Chemical shifts (δ) are given in ppm downfield from tetramethylsilane and coupling constants (J values) are in Hertz. IR spectra were run on a Nicolet Impact 410 Spectrophotometer. A hybrid QSTAR XL quadrupole/time of flight spectrometer was used for HRMS analyses. GC-MS spectra were performed using a Hewlett-Packard 5890 series II mass detector. A Helios-α UV-320 from Thermo-Spectronic was used for UV spectra.
9
Silica Gel Chromatography and NMR Characterization
10
Comprehensive Analytical Characterization Protocol
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Reagents were used as purchased without further purification. Solvents (dichloromethane, methanol, acetonitrile, toluene, ethanol, ethyl acetate) were dried and stored using molecular sieves. TLC was performed on precoated silica gel polyester plates (0.25 mm thickness) through the use of a UV fluorescence indicator 254 (Polychrom SI F254). Chromatographic separations were performed on silica gel columns via flash (Kieselgel 40, 0.040–0.063 mm; Merck, Rahway, NJ, USA) chromatography. The compound/stationary phase ratio was 1g of compound/50 g of silica gel. 1H NMR and 13C NMR spectra were recorded in CDCl3, CD3OD, DMSO-d6, or C3D6O using a Bruker SY spectrometer at 400/100 MHz or a Varian Mercury 400/100 MHz spectrometer. DEPT-135 and DEPT-90 spectra were recorded to identify the C, CH, CH2, and CH3 signals (Figures S1–S16 in Supplementary Materials ). Chemical shifts (δ) are given in ppm downfield from tetramethylsilane, and coupling constants (J values) are given in Hz. IR spectra in KBr disks were run on a Nicolet Impact 410 Spectrophotometer (see Figures S17–S32 in Supplementary Materials ). A hybrid QSTAR XL quadrupole/time of flight spectrometer was used for HRMS analyses. The aqueous solubility of the compounds was determined in a Helios Alfa Spectrophotometer from Thermo-Spectronic.
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