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Molbank, Volume 2017, Issue 1 (March 2017)

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Editorial

Jump to: Research, Other

Open AccessEditorial Acknowledgement to Reviewers of Molbank in 2016
Molbank 2017, 2017(1), M926; doi:10.3390/M926
Received: 11 January 2017 / Accepted: 11 January 2017 / Published: 11 January 2017
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Abstract
The editors of Molbank would like to express their sincere gratitude to the following reviewers for assessing manuscripts in 2016.[...] Full article

Research

Jump to: Editorial, Other

Open AccessCommunication Oxidative Radical Cyclization–Cyclization Reaction Leading to 1H-Benzo[f]isoindole Derivatives
Molbank 2017, 2017(1), M929; doi:10.3390/M929
Received: 22 December 2016 / Revised: 25 January 2017 / Accepted: 2 February 2017 / Published: 4 February 2017
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Abstract
The synthesis of 1H-benzo[f]isoindole derivatives was achieved by the cascade radical cyclization–cyclization reaction of the active methine substrate having an allyl group and phenyl group as different two radical acceptors. This oxidative transformation proceeded by using iron(III) chloride FeCl
[...] Read more.
The synthesis of 1H-benzo[f]isoindole derivatives was achieved by the cascade radical cyclization–cyclization reaction of the active methine substrate having an allyl group and phenyl group as different two radical acceptors. This oxidative transformation proceeded by using iron(III) chloride FeCl3 as a mild oxidant via the intramolecular radical addition to the allyl group followed by the second radical addition to the phenyl group. Full article
(This article belongs to the Section Organic Synthesis)
Figures

Open AccessCommunication (5-Chloroquinolin-8-yl)-2-fluorobenzoate. The Halogen Bond as a Structure Director
Molbank 2017, 2017(1), M934; doi:10.3390/M934
Received: 16 January 2017 / Revised: 8 February 2017 / Accepted: 28 February 2017 / Published: 9 March 2017
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Abstract
Structures containing 8-hydroxyquinoline scaffold are useful for anticancer drug development. The title ester (5-chloroquinolin-8-yl)-2-fluorobenzoate was prepared by the reaction of 2-fluorobenzoyl chloride with 5-chloro-8-hydroxyquinoline. The structure of the title compound was assigned by diverse spectroscopic techniques. Moreover, a crystallographic study was undertaken and
[...] Read more.
Structures containing 8-hydroxyquinoline scaffold are useful for anticancer drug development. The title ester (5-chloroquinolin-8-yl)-2-fluorobenzoate was prepared by the reaction of 2-fluorobenzoyl chloride with 5-chloro-8-hydroxyquinoline. The structure of the title compound was assigned by diverse spectroscopic techniques. Moreover, a crystallographic study was undertaken and its supramolecular characteristics were analyzed. Thus, the central ester fragment C8/O1/C10(O2)/C11 is almost planar with a root mean square (r.m.s.) deviation of 0.0612 Å and it makes dihedral angles of 76.35(6)° and 12.89(11)°, with quinoline and phenyl rings respectively. The structure shows C–H...X (X = halogen) non-classical hydrogen bonds. It also has a halogen…halogen distance less than the sum of the van der Waals radii (3.2171(15) Å). As a result of interactions with halogen atoms, chains of centrosymmetric dimer that form edge-fused R22(18) rings run parallel to the plane (100). Full article
(This article belongs to the Section Structure Determination)
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Figure 1

Other

Jump to: Editorial, Research

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
Received: 2 December 2016 / Revised: 19 December 2016 / Accepted: 20 December 2016 / Published: 27 December 2016
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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
(This article belongs to the Section Organic Synthesis)
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Scheme 1

Open AccessShort Note 4-Chloro-6-ethoxy-2-(methylthio)pyrimidine
Molbank 2017, 2017(1), M923; doi:10.3390/M923
Received: 1 December 2016 / Revised: 22 December 2016 / Accepted: 26 December 2016 / Published: 29 December 2016
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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
(This article belongs to the Section Organic Synthesis)
Figures

Scheme 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
Received: 1 December 2016 / Revised: 23 December 2016 / Accepted: 28 December 2016 / Published: 30 December 2016
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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
[...] Read more.
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
(This article belongs to the Section Structure Determination)
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Open AccessShort Note Ethyl({[acryloyl(furan-2-ylmethyl)amino]acetyl}amino)acetate
Molbank 2017, 2017(1), M925; doi:10.3390/M925
Received: 21 September 2016 / Revised: 26 December 2016 / Accepted: 4 January 2017 / Published: 9 January 2017
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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
[...] Read more.
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
(This article belongs to the Section Organic Synthesis)
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Open AccessShort Note (Z)-4-(Carbomethoxymethylene)-2-(4-fluorophenyl)-4H-benzo[d][1,3]oxazine
Molbank 2017, 2017(1), M927; doi:10.3390/M927
Received: 20 December 2016 / Revised: 5 January 2017 / Accepted: 9 January 2017 / Published: 13 January 2017
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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.
[...] Read more.
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
(This article belongs to the Section Organic Synthesis)
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Figure 1

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
Received: 13 December 2016 / Revised: 11 January 2017 / Accepted: 13 January 2017 / Published: 18 January 2017
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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
[...] Read more.
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
(This article belongs to the Section Organic Synthesis)
Figures

Scheme 1

Open AccessShort Note 2-(tert-Butyl)-4-phenyloxetane
Molbank 2017, 2017(1), M930; doi:10.3390/M930
Received: 22 December 2016 / Revised: 24 January 2017 / Accepted: 7 February 2017 / Published: 10 February 2017
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Abstract
The two geometric isomers of 2-(tert-butyl)-4-phenyloxetane have, for the first time, been prepared starting from the commercially available 4,4-dimethyl-1-phenylpentane-1,3-dione. The latter was reduced with NaBH4 to give a mixture of diastereomeric syn and anti diols which were then stereospecifically cyclized
[...] Read more.
The two geometric isomers of 2-(tert-butyl)-4-phenyloxetane have, for the first time, been prepared starting from the commercially available 4,4-dimethyl-1-phenylpentane-1,3-dione. The latter was reduced with NaBH4 to give a mixture of diastereomeric syn and anti diols which were then stereospecifically cyclized into the corresponding oxetanes with an overall yield for the two steps of 69.6%. The newly synthesized stereoisomeric four-membered oxygenated heterocycles were separated by column chromatography on silica gel and fully spectroscopically characterized. Full article
(This article belongs to the Section Organic Synthesis)
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Open AccessShort Note Copper 5,10,15,20-Tetrakis-(3,4-dibenzyloxyphenyl)porphyrin
Molbank 2017, 2017(1), M931; doi:10.3390/M931
Received: 15 December 2016 / Revised: 6 February 2017 / Accepted: 8 February 2017 / Published: 16 February 2017
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Abstract
The copper complex of 5,10,15,20-tetrakis-(3,4-dibenzyloxyphenyl)porphyrin (CuTDBOPP) was synthesized and characterized with electronic absorption spectroscopy and ESI high-resolution spectrometry. In the electronic spectrum, there was a shift in the Soret band from 424 nm to 420 nm that indicated that the insertion of the
[...] Read more.
The copper complex of 5,10,15,20-tetrakis-(3,4-dibenzyloxyphenyl)porphyrin (CuTDBOPP) was synthesized and characterized with electronic absorption spectroscopy and ESI high-resolution spectrometry. In the electronic spectrum, there was a shift in the Soret band from 424 nm to 420 nm that indicated that the insertion of the metal ion was successful. Additionally, the number of Q bands decreased from four peaks to a single peak at 541 nm. The molar absorptivity of the Soret and Q band are 3.4 × 105 cm−1·M−1 and 1.8 × 105 cm−1·M−1, respectively. The ESI HRMS was in excellent agreement with simulated isotopic distribution spectra. CuTDBOPP was incorporated into a series of Gratzel cells where the open current voltage was recorded. Full article
(This article belongs to the Section Organic Synthesis)
Figures

Open AccessShort Note 3-{4-[(E)-{4-[(E)-Phenyldiazenyl]phenyl}diazenyl]phenoxy}propane-1,2-diol
Molbank 2017, 2017(1), M932; doi:10.3390/M932
Received: 13 January 2017 / Revised: 7 February 2017 / Accepted: 10 February 2017 / Published: 22 February 2017
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Abstract
Title compound was designed to be a black quencher of pyrene fluorescence. It was made amphiphilic to serve as a membrane-bound probe. The synthesis is a two-step procedure. The first step is a Mitsunobu reaction of [{(phenyldiazenyl)phenyl}diazenyl]phenol with 1,2-O-isopropylideneglycerol. The second
[...] Read more.
Title compound was designed to be a black quencher of pyrene fluorescence. It was made amphiphilic to serve as a membrane-bound probe. The synthesis is a two-step procedure. The first step is a Mitsunobu reaction of [{(phenyldiazenyl)phenyl}diazenyl]phenol with 1,2-O-isopropylideneglycerol. The second step is the cleavage of the isopropylidene protecting group. The title compound has the extinction coefficient 59,000 at λmax = 380 nm. The Forster distance between the title compound and the pyrene was found to be 37.8 Å. Full article
(This article belongs to the Section Organic Synthesis)
Figures

Figure 1

Open AccessShort Note Dimethyl 7-(dimethylamino)-3,4-dihydro-1-(2-oxopropyl)-4-phenylnaphthalene-2,2(1H)-dicarboxylate
Molbank 2017, 2017(1), M933; doi:10.3390/M933
Received: 10 January 2017 / Revised: 28 February 2017 / Accepted: 1 March 2017 / Published: 3 March 2017
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Abstract
A Friedel-Crafts–type ring-opening/intramolecular Michael addition cascade reaction of (E)-4-(3-(dimethylamino)phenyl)but-3-en-2-one with dimethyl 2-phenylcyclopropane-1,1-dicarbo-xylate catalyzed by Yb(OTf)3 has produced a new compound, dimethyl 7-(dimethylamino)-3,4-dihydro-1-(2-oxopropyl)-4-phenylnaphthalene-2,2(1H)-dicarboxylate. This reaction provided diastereoslective trans tetralin (7:3 dr) on the cyclohexyl ring. The structure of the
[...] Read more.
A Friedel-Crafts–type ring-opening/intramolecular Michael addition cascade reaction of (E)-4-(3-(dimethylamino)phenyl)but-3-en-2-one with dimethyl 2-phenylcyclopropane-1,1-dicarbo-xylate catalyzed by Yb(OTf)3 has produced a new compound, dimethyl 7-(dimethylamino)-3,4-dihydro-1-(2-oxopropyl)-4-phenylnaphthalene-2,2(1H)-dicarboxylate. This reaction provided diastereoslective trans tetralin (7:3 dr) on the cyclohexyl ring. The structure of the newly synthesized compound was determined using 1H-, 13C-NMR, IR and mass spectral data. Full article
(This article belongs to the Section Organic Synthesis)
Figures

Scheme 1

Open AccessShort Note Methyl 2,3,6-tri-O-Benzoyl-4-O-(tert-butyldimethylsilyl)-β-d-galactopyranoside
Molbank 2017, 2017(1), M935; doi:10.3390/M935
Received: 22 February 2017 / Revised: 15 March 2017 / Accepted: 16 March 2017 / Published: 19 March 2017
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Abstract
Methyl 2,3,6-tri-O-benzoyl-4-O-(tert-butyldimethylsilyl)-β-d-galactopyranoside was synthesized in 47% yield by the silylation of a partially benzoylated galactose derivative, prepared from methyl β-d-galactopyranoside. The product was characterized by 1H-NMR, 13C-NMR, IR and mass spectrometry. Full article
(This article belongs to the Section Organic Synthesis)
Figures

Scheme 1

Open AccessShort Note 5,9,11-Trihydroxy-2,2-dimethyl-3-(2-methylbut-3-en-2-yl)pyrano[2,3-a]xanthen-12(2H)-one from the Stem Bark of Calophyllum tetrapterum Miq.
Molbank 2017, 2017(1), M936; doi:10.3390/M936
Received: 15 February 2017 / Revised: 17 March 2017 / Accepted: 18 March 2017 / Published: 21 March 2017
Cited by 1 | PDF Full-text (826 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A new pyranoxanthone namely 5,9,11-trihydroxy-2,2-dimethyl-3-(2-methylbut-3-en-2-yl)pyrano[2,3-a]xanthen-12(2H)-one (1) was isolated from the stem bark of Calophyllum tetrapterum Miq. The structure of compound 1 was determined by means of spectroscopic methods including UV, IR, HRESIMS, 1D and 2D NMR. Full article
(This article belongs to the Section Natural Products)
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Figure 1

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