Open AccessShort Note
Ethyl (1R*,10S*,12R*,15S*)-4-Hydroxy-2-oxo-15- (2-oxo-1-pyrrolidinyl)-9-oxatetracyclo[10.2.2.01,10.03,8]hexadeca-3,5,7,13-tetraene-13-carboxylate
Molbank 2017, 2017(1), M928; doi:10.3390/M928 -
Abstract
N-Vinylpirrolidinone reacts with (E)-ethyl 5-hydroxy-3-(4-oxo-4H-chromen-3-yl) acrylate (1) through a domino reaction similar to that reported reaction for ethyl vinyl ether. Inverse electron demand Diels–Alder (IEDDA)–elimination-IEDDA generates isomeric tetracycles 5 and 6. The assignment of the
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N-Vinylpirrolidinone reacts with (E)-ethyl 5-hydroxy-3-(4-oxo-4H-chromen-3-yl) acrylate (1) through a domino reaction similar to that reported reaction for ethyl vinyl ether. Inverse electron demand Diels–Alder (IEDDA)–elimination-IEDDA generates isomeric tetracycles 5 and 6. The assignment of the relative stereochemistry of the products was made by comparing the proton couplings with those obtained by reaction with ethyl vinyl ether. Full article
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Scheme 1

Open AccessShort Note
(Z)-4-(Carbomethoxymethylene)-2-(4-fluorophenyl)-4H-benzo[d][1,3]oxazine
Molbank 2017, 2017(1), M927; doi:10.3390/M927 -
Abstract
The title compound, (Z)-4-(carbomethoxymethylene)-2-(4-fluorophenyl)-4H-benzo[d][1,3]oxazine, was synthesized in 68% isolated yield by palladium-catalyzed oxidative cyclization-methoxycarbonylation of 4-fluoro-N-(2-((trimethylsilyl)ethynyl)phenyl)benzamide. This new heterocyclic derivative was fully characterized by IR, 1H-NMR, 13C-NMR spectroscopies, MS spectrometry, and elemental analysis.
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The title compound, (Z)-4-(carbomethoxymethylene)-2-(4-fluorophenyl)-4H-benzo[d][1,3]oxazine, was synthesized in 68% isolated yield by palladium-catalyzed oxidative cyclization-methoxycarbonylation of 4-fluoro-N-(2-((trimethylsilyl)ethynyl)phenyl)benzamide. This new heterocyclic derivative was fully characterized by IR, 1H-NMR, 13C-NMR spectroscopies, MS spectrometry, and elemental analysis. The Z configuration around the double bond was unequivocally established by 2D NOESY experiments. Full article
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Figure 1

Open AccessEditorial
Acknowledgement to Reviewers of Molbank in 2016
Molbank 2017, 2017(1), M926; doi:10.3390/M926 -
Abstract The editors of Molbank would like to express their sincere gratitude to the following reviewers for assessing manuscripts in 2016.[...] Full article
Open AccessShort Note
Ethyl({[acryloyl(furan-2-ylmethyl)amino]acetyl}amino)acetate
Molbank 2017, 2017(1), M925; doi:10.3390/M925 -
Abstract
Ethyl({[acryloyl(furan-2-ylmethyl)amino]acetyl}amino)acetate was synthesized via Ugi four component (4C) reaction at ambient temperature. The protocol employs a reaction between formaldehyde, furfurylamine, acrylic acid, and ethyl 2-isocyanoacetate. The course of the reaction was found to be high yielding, and the resulting glycine ester derivative was
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Ethyl({[acryloyl(furan-2-ylmethyl)amino]acetyl}amino)acetate was synthesized via Ugi four component (4C) reaction at ambient temperature. The protocol employs a reaction between formaldehyde, furfurylamine, acrylic acid, and ethyl 2-isocyanoacetate. The course of the reaction was found to be high yielding, and the resulting glycine ester derivative was well characterized by elemental analysis, FTIR, NMR spectroscopy, and mass spectrometric techniques. Full article
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Figure 1

Open AccessShort Note
(E)-1-(2-Aminophenyl)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one
Molbank 2017, 2017(1), M924; doi:10.3390/M924 -
Abstract
The title chalcone (E)-1-(2-aminophenyl)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one was obtained in 76% yield from a NaOH catalyzed Claisen–Schmidt condensation reaction between o-aminoacetophenone and piperonal. This product will be used as a key precursor for the development of an alternative route for the
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The title chalcone (E)-1-(2-aminophenyl)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one was obtained in 76% yield from a NaOH catalyzed Claisen–Schmidt condensation reaction between o-aminoacetophenone and piperonal. This product will be used as a key precursor for the development of an alternative route for the total synthesis of the alkaloid Graveoline. Single crystals of the title compound suitable for X-ray diffraction were grown via slow evaporation in ethanol at room temperature. A complete crystallographic study was performed in depth to unequivocally confirm its structure. The crystal structure of the title o-aminochalcone, C16H13NO3, shows two molecules per asymmetric unit (Z = 4) and adopts an E configuration about the C=C double bond. In the title compound, the mean plane of the non-H atoms of the central chalcone fragment C—C(O)—C—C—C is as follow: [root-mean-square (r.m.s.) deviation = 0.0210 Å for A–B and 0.0493 for C–D molecules]. In the crystal, molecules are linked by N–H...O and C–H...O, hydrogen bonds forming S(6), R22(6) and edge-fused R44(24)rings along with C(18) chains running parallel to (110). Full article
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Figure 1

Open AccessShort Note
4-Chloro-6-ethoxy-2-(methylthio)pyrimidine
Molbank 2017, 2017(1), M923; doi:10.3390/M923 -
Abstract 4,6-Dichloro-2-(methylthio)pyrimidine (3) reacts with EtONa in EtOH, at ca. 20 °C, for 2 h, to give exclusively 4-chloro-6-ethoxy-2-(methylthio)pyrimidine (5) in 89% yield. The latter is presented as a useful multifunctionalised pyrimidine scaffold. Full article
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Scheme 1

Open AccessShort Note
(2E,2′E)-3-(4-{[4-(4-Hydroxy-3-methoxyphenyl)but-2-en-1-yl]oxy}phenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
Molbank 2017, 2017(1), M922; doi:10.3390/M922 -
Abstract A hybrid of eugenol and a chalcone has been synthesized in good yield via cross olefin metathesis. The title compound (3) was characterized by spectroscopic data including NMR, infrared, and ESI-MS. Full article
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Scheme 1

Open AccessShort Note
N-[2-(Cyclohexylamino)-2-oxoethyl]-N-(4-octyloxy)phenyl-prop-2-enamide
Molbank 2016, 2016(4), M921; doi:10.3390/M921 -
Abstract
N-[2-(Cyclohexylamino)-2-oxoethyl]-N-(4-octyloxy)phenyl-prop-2-enamide was prepared in good yield by coupling of 4(octyloxy)aniline, Cyclohexyl isocyanide, paraformaldehyde and acrylic acid by multicomponent Ugi reaction, at room temperature. The structure of the newly synthesized tripeptoid derivative was well characterized using elemental analysis, FTIR, NMR and
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N-[2-(Cyclohexylamino)-2-oxoethyl]-N-(4-octyloxy)phenyl-prop-2-enamide was prepared in good yield by coupling of 4(octyloxy)aniline, Cyclohexyl isocyanide, paraformaldehyde and acrylic acid by multicomponent Ugi reaction, at room temperature. The structure of the newly synthesized tripeptoid derivative was well characterized using elemental analysis, FTIR, NMR and mass spectral data. Full article
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Figure 1

Open AccessShort Note
3-(2-Hydroxyethyl)-2-methylbenzothiazolium Bromide
Molbank 2016, 2016(4), M920; doi:10.3390/M920 -
Abstract A novel method for the preparation of 3-(2-hydroxyethyl)-2-methylbenzothiazolium bromide was developed. It consists of heating of 2-methylbenzothiazole, 2-bromoethanol and ethoxyethanol for 2 h. On the next day the precipitate was filtered and air dried. Full article
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Scheme 1

Open AccessShort Note
1,4-Dihydro-4-(nitromethyl)-2-phenyl-1-tosylquinoline-3-carbaldehyde
Molbank 2016, 2016(4), M918; doi:10.3390/M918 -
Abstract An aza-Michael/Michael cascade reaction of 2-((E)-2-nitrovinyl)-N-tosylbenzenamine with 3-phenylpropiolaldehyde catalyzed by pyrrolidine has produced a new compound, 1,4-dihydro-4-(nitromethyl)-2-phenyl-1-tosylquinoline-3-carbaldehyde. The structure of the newly synthesized compound was determined using 1H, 13C-NMR, IR, and mass spectral data. Full article
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Open AccessShort Note
3-Ethyl-2-(ethylimino)-4-methyl-2,3-dihydro-1,3-thiazole-5-carboxylate Ethyl Ester
Molbank 2016, 2016(4), M919; doi:10.3390/M919 -
Abstract
An efficient procedure to obtain the new compound 1a from ethyl acetoacetate (2a), NBS and N,N′-diethylthiourea (4a) was reported. In comparison with the traditional method to synthesize its analogues, this efficient, catalyst-free, and one-pot synthetic method
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An efficient procedure to obtain the new compound 1a from ethyl acetoacetate (2a), NBS and N,N′-diethylthiourea (4a) was reported. In comparison with the traditional method to synthesize its analogues, this efficient, catalyst-free, and one-pot synthetic method is facile. The work-up procedure is easy and gives the pure target compound under milder reaction conditions in a relatively high yield of 75%. Full article
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Scheme 1

Open AccessShort Note
1,3,1′,3′-(Dinaphthalene-1,8-diyl)bisthiourea
Molbank 2016, 2016(4), M917; doi:10.3390/M917 -
Abstract
A new bisthiourea compound, 1,3,1′,3′-(dinaphthalene-1,8-diyl)bisthiourea, was synthesized. Its structure was characterized by elemental analysis, FT-IR and 1H-, 13C-NMR and MS spectroscopic techniques. The compound was found to selectively recognize fluoride anions among other halides as demonstrated by means of UV-vis absorption
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A new bisthiourea compound, 1,3,1′,3′-(dinaphthalene-1,8-diyl)bisthiourea, was synthesized. Its structure was characterized by elemental analysis, FT-IR and 1H-, 13C-NMR and MS spectroscopic techniques. The compound was found to selectively recognize fluoride anions among other halides as demonstrated by means of UV-vis absorption spectroscopic date and the naked eye. Full article
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Open AccessCommunication
2-C-Alkynyl and 2-C-cis-Alkenyl β-Mannosides with Acetal Protected γ-Aldehyde Functionality via 2-Uloside Alkynylation and Lindlar Hydrogenation
Molbank 2016, 2016(4), M916; doi:10.3390/M916 -
Abstract
Benzyl 3,4,6-tri-O-benzyl-β-d-arabino-hexos-2-ulo-1,5-pyranoside was subjected to manno-selective ketone alkynylation with propiolaldehyde dibenzyl acetal, resulting in the formation of a 2-C-alkynyl β-mannoside bearing a γ-dibenzyl acetal functionality. Subsequent transacetalization of the acetal moiety with methanol and
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Benzyl 3,4,6-tri-O-benzyl-β-d-arabino-hexos-2-ulo-1,5-pyranoside was subjected to manno-selective ketone alkynylation with propiolaldehyde dibenzyl acetal, resulting in the formation of a 2-C-alkynyl β-mannoside bearing a γ-dibenzyl acetal functionality. Subsequent transacetalization of the acetal moiety with methanol and 1,3-dihydroxypropane and acetylation of position 2, respectively, gave 4 different 2-C-alkynyl branched mannosides. Lindlar hydrogenation of the latter under optimized conditions in dimethylformamide afforded a series of 2-C-cis-alkenyl mannosides. X-ray molecular structures of benzyl 3,4,6-tri-O-benzyl-β-d-arabino-hexos-2-ulo-1,5-pyranoside and of the branched glycoside benzyl 3,4,6-tri-O-benzyl-2-C-((Z)-3,3-dibenzyloxyprop-1-en-1-yl)-β-d-mannopyranoside are reported. Full article
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Open AccessShort Note
(3,5-Dimethylpyrazol-1-yl)-[4-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)phenyl]methanone
Molbank 2016, 2016(4), M915; doi:10.3390/M915 -
Abstract
In an attempt to enhance cytotoxic activity of pyrazolo[3,4-d]pyrimidine core, we synthesized (3,5-dimethylpyrazol-1-yl)-[4-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)phenyl]methanone (4) by reacting 4-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)benzohydrazide (3) with acetylacetone. Antiproliferative activity of this compound was screened against breast
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In an attempt to enhance cytotoxic activity of pyrazolo[3,4-d]pyrimidine core, we synthesized (3,5-dimethylpyrazol-1-yl)-[4-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)phenyl]methanone (4) by reacting 4-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)benzohydrazide (3) with acetylacetone. Antiproliferative activity of this compound was screened against breast (MCF-7), colon (HCT-116), and liver (HEPG-2) cancer cell lines. The tested compound exhibited cytotoxic activity with IC50 = 5.00–32.52 μM. Moreover, inhibitory activity of this compound was evaluated against the epidermal growth factor receptor (EGFR), the fibroblast growth factor receptor (FGFR), the insulin receptor (IR), and the vascular endothelial growth factor receptor (VEGFR). This target compound showed potent inhibitory activity, especially against FGFR with IC50 = 5.18 μM. Full article
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Open AccessShort Note
4,4′-Bis[4-(4′-hydroxyphenyl)phenylazo]diphenyl Ether
Molbank 2016, 2016(4), M914; doi:10.3390/M914 -
Abstract 4,4′-Bis[4-(4′-hydroxyphenyl)phenylazo]diphenyl ether (3) was prepared by diazotization coupling of 4,4′-oxy dianiline (1) and biphenyl-4-ol (2). The synthesized compound (3) was characterized by elemental analysis, UV-Visible, FTIR and 1H-NMR (nuclear magnetic resonance) spectroscopic studies. Full article
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Open AccessCommunication
4-Acetyl-2-hydroxy-2,5-dimethylfuran-3(2H)-one
Molbank 2016, 2016(4), M913; doi:10.3390/M913 -
Abstract The facile synthesis of 4-acetyl-2-hydroxy-2,5-dimethylfuran-3(2H)-one (4) was achieved by the Mn(OAc)3-mediated aerobic oxidation of 2,4-pentanedione or the direct reaction of Mn(acac)3 in AcOH-TFE at room temperature under a dried air stream. Full article
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Open AccessShort Note
Benzyl 2-((E)-Tosyliminomethyl)phenylcarbamate
Molbank 2016, 2016(4), M912; doi:10.3390/M912 -
Abstract Benzyl 2-((E)-tosyliminomethyl)penylcarbamate was prepared in good yield and characterized by the condensation reaction of benzyl 2-formylphenylcarbamate with p-toluenesulfonyl amine. The structure of the newly synthesized compound was determined using 1H, 13C-NMR, IR and mass spectral data. Full article
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Open AccessShort Note
(E)-1-(2-Aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one
Molbank 2016, 2016(4), M911; doi:10.3390/M911 -
Abstract
The title chalcone (E)-1-(2-aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one was prepared with an excellent yield from a Claisen–Schmidt condensation reaction between o-aminoacetophenone and p-chlorobenzaldehyde. This product will be used as a key precursor for the development of an alternative route for the total synthesis
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The title chalcone (E)-1-(2-aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one was prepared with an excellent yield from a Claisen–Schmidt condensation reaction between o-aminoacetophenone and p-chlorobenzaldehyde. This product will be used as a key precursor for the development of an alternative route for the total synthesis of dubamine and graveoline alkaloids. Single crystals of the title compound suitable for X-ray diffraction were grown via slow evaporation in ethanol at room temperature. A complete crystallographic study was performed in depth to unequivocally confirm its structure and determine some interesting supramolecular properties. The crystal structure of the title o-aminochalcone, C15H12ClNO, shows two molecules per asymmetric unit (Z′ = 2) and adopts an E configuration about the C=C double bond. In the title compound, the mean plane of the non-H atoms of the central chalcone fragment C—C(O)—C—C—C is as follows: [r.m.s. deviation = 0.0130 Å for A-B and 0.0043 for C-D molecules]. In the crystal, molecules are linked by N—H...N and C—H...O, hydrogen bonds forming edge-fused R66(46) rings parallel to (100). Additionally, N—H...O hydrogen bonds generate a three-dimensional network. Full article
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Figure 1

Open AccessShort Note
5-[(3-Fluorophenyl)(2-hydroxy-6-oxocyclohex-1-en-1-yl)methyl]-6-hydroxy-1,3-dimethylpyrimidine-2,4(1H,3H)-dione
Molbank 2016, 2016(4), M910; doi:10.3390/M910 -
Abstract
5-[(3-Fluorophenyl)(2-hydroxy-6-oxocyclohex-1-en-1-yl)-methyl]-6-hydroxy-1,3-di-methylpyrimidine-2,4(1H,3H)-dione 3 was synthesized via a multicomponent reaction. The Aldol–Michael addition reactions of N,N-dimethylbarbituric acid, cyclohexane-1,3-dione, and 3-fluorobenzaldehyde in aqueous solution gave the product in high yield. The molecular structure of the compound was confirmed by
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5-[(3-Fluorophenyl)(2-hydroxy-6-oxocyclohex-1-en-1-yl)-methyl]-6-hydroxy-1,3-di-methylpyrimidine-2,4(1H,3H)-dione 3 was synthesized via a multicomponent reaction. The Aldol–Michael addition reactions of N,N-dimethylbarbituric acid, cyclohexane-1,3-dione, and 3-fluorobenzaldehyde in aqueous solution gave the product in high yield. The molecular structure of the compound was confirmed by spectroscopic methods and X-ray crystallography. The title compound (C19H19FN2O5·H2O) crystallizes in the Monoclinic form, P21/c, a = 7.8630 (5) Å, b = 20.0308 (13) Å, c = 11.3987 (8) Å, β = 104.274 (3)°, V = 1739.9 (2)° Å3, Z = 4, Rint = 0.117, wR(F2) = 0.124, T = 100 K. Full article
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Open AccessCommunication
Straightforward Synthesis of 2(5H)-Furanones as Promising Cross-Coupling Partners: Direct Furanone Annulation Utilizing Ti-Mediated Aldol Addition
Molbank 2016, 2016(4), M908; doi:10.3390/M908 -
Abstract
Direct 2(5H)-furanone annulation produces promising cross-coupling partners incorporating m- or p-bromo- and p-tosyloxyphenyl groups into the 5-position of a notable 2(5H)-furanone pharmacore. The present one-pot annulation method involves two distinctive reactions: (i) a powerful and crossed
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Direct 2(5H)-furanone annulation produces promising cross-coupling partners incorporating m- or p-bromo- and p-tosyloxyphenyl groups into the 5-position of a notable 2(5H)-furanone pharmacore. The present one-pot annulation method involves two distinctive reactions: (i) a powerful and crossed Ti-direct aldol addition and (ii) an acid-induced characteristic cyclo-condensation, leading to 2(5H)-furanones. Suzuki-Miyaura cross-coupling of 5-(4-bromophenyl)-furan-2(5H)-ones, 5-(4-tosyloxyphenyl)-3,4-dimethylfuran-2(5H)-ones and a furan derivative successfully afforded the corresponding products with the 2(5H)-furanone skeleton. Full article
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