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Letters in Organic Chemistry
ISSN: 1570-1786
Letters in Organic Chemistry
Volume 7, Number 3, April 2010
Contents
Graphical
Abstracts Pp. i-v
Editor’s Choice
Synthesis of Methyl 4-O-methyl-β-D-ribo-hex-3-ulopyranoside-1-13C
and Methyl 4-O-methyl-β-D-ribo-hex-3-ulopyranoside-3-13C
as Fragment Analogues of Oxidized Cellulose Units Pp.
186-190
Karin Krainz, Andreas Hofinger, Thomas Dietz,
Hans-Ulrich Süss, Antje Potthast and Thomas
Rosenau
[Abstract] [Purchase
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Synthesis Optimization of Hydroxymethylnitrofurazone,
an Antichagasic Candidate, Using 32
Factorial Design Pp. 191-195
Gustavo H.G. Trossini, Jeanine Giarolla,
Leandro de Rezende, Antonia T. do Amaral, Marcio H. Zaim,
Roy E. Bruns and Elizabeth I. Ferreira
[Abstract] [Purchase
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A Procedure for Facile Synthesis of Nucleosides Using
N, O-Bistrimethyl-silylacetamide in the Presence of Natural
Phosphate Coated with Potassium Iodide Pp. 196-199
Laila Baddi, Michael Smietana, Saïd
Sebti, Jean-Jacques Vasseur and Hassan B. Lazrek
[Abstract] [Purchase
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Synthesis of New Dinucleotide mRNA Cap Analogs Containing
2, 6-Diaminopurine Moiety Pp. 200-202
Anilkumar R. Kore and Irudaya Charles
[Abstract] [Purchase
Article]
Design, Synthesis and Optical Response of Pyridine-Cored
V-Shaped Stilbenoid Dendrimers Pp. 203-207
Debabrata Jana and Binay K. Ghorai
[Abstract] [Purchase
Article]
Niobium (V) Chloride: An Efficient Catalyst for the
Synthesis of Quinoxalines Pp. 208-211
Y. Venkateswarlu and P. Leelavathi
[Abstract] [Purchase
Article]
Oxazolidin-2-one as Efficient Ligand for the Copper-Catalyzed
N-Arylation of Pyrrole, Imidazole and Indole
Pp. 212-218
Hengchang Ma, Shang Wu, Qiangsheng Sun and
Ziqiang Lei
[Abstract] [Purchase
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Chiral Phosphoric Acid Catalyzed Diastereo- and Enantioselective
1,4-Conjugate Addition of β-Ketoesters
to Nitroolefins Pp. 219-225
Hui Zhang, Lin-Feng Cun, Xiao-Mei Zhang
and Wei-Cheng Yuan
[Abstract] [Purchase
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An Approach to Synthesis of 3-Aryl-2-Oxazolidinones
and In Situ ‘Click’ Assembly of 1,2,3-Triazole
Oxazolidinones Pp. 226-228
Xingxian Zhang, Cheng Li, Wei Chen and
Xiang Wu
[Abstract] [Purchase
Article]
Stereoselective Chlorination of New Type Baylis-Hillman
Adducts by bis(Trichloromethyl)carbonate with the
Aid of Catalytic Amount of Triphenylphosphine Oxide
Pp. 229-234
Weihui Zhong, Lingjuan Hong and
Yemin Zheng
[Abstract] [Purchase
Article]
Borane and Platinum Complexes of Benzo-1,3,2-Dioxaphospholane
Derivatives Pp. 235-239
György Keglevich, Andrea Kerényi,
Tamás Körtvélyesi, Krisztina Ludányi
and László Drahos
[Abstract] [Purchase
Article]
Artosimmin- A Potential Anti-Cancer Lead Compound
from Artocarpus odoratissimus Pp. 240-244
Gwendoline C.L. Ee, Siow H. Teo, Mawardi
Rahmani, Chan K. Lim, Yang M. Lim and Choon F.J.
Bong
[Abstract] [Purchase
Article]
The First Kinetic Enzymatic Resolution of Methyl Ester
of C75 Pp. 245-248
Kuheli Chakrabarty, Cristina Forzato, Patrizia
Nitti, Giuliana Pitacco and Ennio Valentin
[Abstract] [Purchase
Article]
Metal-Free Oxidation of Urazole and 1,4-Dihydropyridine Derivatives
Under Mild and Heterogeneous Conditions by Nitro Urea, Derived
from Urea Nitrate and Silica Sulfuric Acid Pp. 249-254
Arash Ghorbani-Choghamarani, Mohammad A.
Zolfigol, Maryam Hajjami, Shahrbanoo Rastgoo and
Shadpour Mallakpour
[Abstract] [Purchase
Article]
Montmorillonite K-10: As a Useful Catalyst in Organic
Preparations Pp. 255-268
Bita Baghernejad
[Abstract] [Purchase
Article]
Animal Bone Meal (ABM): A Novel Natural Catalyst for Thia-Michael
Addition Pp. 269-271
Yassine Riadi, Rachid Mamouni, Younes Abrouki,
Mohammadine El Haddad, Nabil Saffaj, Said El Antri, Sylvain
Routier, Gérald Guillaumet and Said Lazar
[Abstract] [Purchase
Article]
Abstracts
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Synthesis of Methyl 4-O-methyl-β-D-ribo-hex-3-ulopyranoside-1-13C
and Methyl 4-O-methyl-β-D-ribo-hex-3-ulopyranoside-3-13C
as Fragment Analogues of Oxidized Cellulose Units
Karin Krainz, Andreas Hofinger, Thomas Dietz,
Hans-Ulrich Süss, Antje Potthast and Thomas
Rosenau
Model compounds of oxidized anhydroglucose units in cellulosic
materials, carrying 13C
isotopic labels at specific positions, have been synthesized
starting from commercially available 1-13C-D-glucose
(14.7%) and 3-13C-D-glucose
(6.3%), respectively, over 10 linear steps. To ensure high
yields, the synthetic route was optimized with non-labeled
material beforehand. The labeled compounds are used in studies
of chromophore formation, yellowing, brightness reversion
and aging of cellulosics.
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Synthesis Optimization of Hydroxymethylnitrofurazone,
an Antichagasic Candidate, Using 32
Factorial Design
Gustavo H.G. Trossini, Jeanine Giarolla,
Leandro de Rezende, Antonia T. do Amaral, Marcio H. Zaim,
Roy E. Bruns and Elizabeth I. Ferreira
Hydroxymethylnitrofurazone presents in vitro activity
against Trypanosoma cruzi. The optimization of the
synthesis of this compound was performed through a 32
factorial statistical design. Quadratic model produced the
best response surface predicting a maximum yield (82%) close
to the center design point with a seven hours reaction and
a 1:1.5 (NF:K2CO3)
ratio.
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A Procedure for Facile Synthesis of Nucleosides Using
N, O-Bistrimethyl-silylacetamide in the Presence of Natural
Phosphate Coated with Potassium Iodide
Laila Baddi, Michael Smietana, Saïd
Sebti, Jean-Jacques Vasseur and Hassan B. Lazrek
Several α-D/L-arabino
and β-D/L-
xylonucleosides were synthesized in good yields under mild
conditions by N-glycosylation of 1-O-acetyl D/L- arabino,
and xylofuranose, with silylated nucleobases (uracil, thymine
and 6-azauracil) in acetonitrile using natural phosphate (NP)
coated with potassium iodide in BSA as catalyst.
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Synthesis of New Dinucleotide mRNA Cap Analogs Containing
2, 6-Diaminopurine Moiety
Anilkumar R. Kore and Irudaya Charles
The first example of the synthesis of cap analog derivatives
having 2, 6-diaminopurine nucleoside has been described. The
desired modified cap analogs m7G[5']ppp[5']2-aminoA
6 and m27,3'OG[5']ppp[5']
2-aminoA 7 were obtained
from the coupling reaction of imidazolide salt of 2-amino
adenosine [5'] monophosphate with its corresponding TEA salt
of m7GDP in the presence
of ZnCl2as a catalyst in
73% and 64% yield, respectively. The structures of new cap
analogs were confirmed by LC/MS, 1H
and 31P NMR.
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Design, Synthesis and Optical Response of Pyridine-Cored
V-Shaped Stilbenoid Dendrimers
Debabrata Jana and Binay K. Ghorai
Design, synthesis and characterization of new series of first-generation
V-shaped dendrimers bearing phenylenevinylene dendritic branches
in periphery and pyridine as a core is described. A preliminary
study of the optical properties of the resulting compounds
was conducted by UV/vis and fluorescence spectroscopy.
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Niobium (V) Chloride: An Efficient Catalyst for the
Synthesis of Quinoxalines
Y. Venkateswarlu and P. Leelavathi
A simple and efficient method for the synthesis of quinoxalines
derivatives has been developed. All the reactions were carried
out in presence of niobium (V) chloride at acetonitrile reflux
conditions. The method is applicable to a variety of diketones
and 1, 2-phenylenediamines to afford the corresponding derivatives
in excellent yields.
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Oxazolidin-2-one as Efficient Ligand for the Copper-Catalyzed
N-Arylation of Pyrrole, Imidazole and Indole
Hengchang Ma, Shang Wu, Qiangsheng Sun and
Ziqiang Lei
Oxazolidin-2-one was found to be a facile ligand for the N-arylation
of pyrrole, indole, and imidazole with aryl and heteroaryl
iodides, bromides, and chlorides by applying CuI as catalyst.
The easy preparation, commercial availability, lower molecular
weight, and broad substrate applicability, as well as substituent
compatibility of this catalysis system render oxazolidin-2-one
great advantages over the Cu-catalyzed methods that have already
been utilized in a number of applications.
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Chiral Phosphoric Acid Catalyzed Diastereo- and Enantioselective
1,4-Conjugate Addition of β-Ketoesters
to Nitroolefins
Hui Zhang, Lin-Feng Cun, Xiao-Mei Zhang
and Wei-Cheng Yuan
Chiral phosphoric acid as organocatalyst for the diastereo-
and enantioselectivity 1,4-conjugate addition of a variety
of β-ketoesters
to nitroolefins was firstly developed, providing the corresponding
adducts in high yield (up to 97%) with moderate diastereoselectivities
(up to 2.6:1 dr) and enantioselectivities (up to 58% ee).
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An Approach to Synthesis of 3-Aryl-2-Oxazolidinones
and In Situ ‘Click’ Assembly of 1,2,3-Triazole
Oxazolidinones
Xingxian Zhang, Cheng Li, Wei Chen and
Xiang Wu
A facile and efficient addition of isocyanates with epoxides
in the presence of MgI2 etherate
was reported in good yields. The corresponding 2-oxazolidinone
could be easily converted into 1,2,3-triazole-oxazolidinone
by click reaction in excellent yield.
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Stereoselective Chlorination of New Type Baylis-Hillman
Adducts by bis(Trichloromethyl)carbonate with the
Aid of Catalytic Amount of Triphenylphosphine Oxide
Weihui Zhong, Lingjuan Hong and
Yemin Zheng
The chlorination of the new type Baylis-Hillman adducts by
bis(trichloromethyl)carbonate (BTC) with the aid
of catalytic amount of triphenylphosphine oxide (Ph3PO)
was achieved with high yields and high stereoselectivities.
A plausible mechanism is presented.
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Borane and Platinum Complexes of Benzo-1,3,2-Dioxaphospholane
Derivatives
György Keglevich, Andrea Kerényi,
Tamás Körtvélyesi, Krisztina Ludányi
and László Drahos
The reaction of P-chloro-benzo-1,3,2-dioxaphospholane with
diethylamine, (S)-(–)-α-phenylethylamine
and (1R,2S,5R)-(–)-menthol
afforded the corresponding amino- and cycloalkoxy derivatives.
The P-(diethylamino)-benzodioxaphospholane was converted
to the corresponding platinum complex of cis-PtL2Cl2
type. It was observed that under not strictly anhydrous conditions,
one of the benzodioxaphospholane rings suffered ring opening.
The stereostructures and the relative energies of the dioxaphospholane-related
platinum complexes were calculated by the B3LYP/6-31G* –
LANL2DZ, as well as the PM6-DH methods. The phenylethylamino-
and menthylbenzodi-oxaphospholanes were stabilized as the
corresponding P-boranes. Decomplexation of a few P-boranes
was studied and the optimum conditions were evaluated.
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Artosimmin- A Potential Anti-Cancer Lead Compound
from Artocarpus odoratissimus
Gwendoline C.L. Ee, Siow H. Teo, Mawardi
Rahmani, Chan K. Lim, Yang M. Lim and Choon F.J.
Bong
Our recent study on Artocarpus odoratissimus (Moraceae)
has resulted in the purification of a new prenylated pyranoflavone
derivative artosimmin (1) and traxateryl
acetate (2). Details of structural elucidations
associated with 1 and 2
are reported by combining 1D, 2D NMR and mass spectrometric
methods. Compound 2 is obtained for the first
time from this species. Furthermore, the biological assay
results exhibited compound 1 to be significantly
cytotoxic against cancer cell lines (HL-60 & MCF-7) and
also possessed antioxidant properties toward 1,1-diphenyl-2-picrylhydrazyl
radical (DPPH).
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The First Kinetic Enzymatic Resolution of Methyl Ester
of C75
Kuheli Chakrabarty, Cristina Forzato, Patrizia
Nitti, Giuliana Pitacco and Ennio Valentin
Enantioselective hydrolysis of methyl ester of (±)-C75
was successfully accomplished by means of Acylase I from Aspergillus
to afford (2R,3S)-(+)-C75 with 96% e.e.
The unreacted methyl ester was recovered with >99% e.e.
This latter compound was either chemically or enzymatically
hydrolyzed to furnish (2S,3R)-(–)-C75
with >99% e.e.
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Metal-Free Oxidation of Urazole and 1,4-Dihydropyridine
Derivatives Under Mild and Heterogeneous Conditions by Nitro
Urea, Derived from Urea Nitrate and Silica Sulfuric Acid
Arash Ghorbani-Choghamarani, Mohammad A.
Zolfigol, Maryam Hajjami, Shahrbanoo Rastgoo and
Shadpour Mallakpour
Mild combination of nitro urea, derived from urea nitrate,
and silica sulfuric acid (SiO2OSO3H)
might act as an efficient oxidizing media, which could be
able to oxidize different types of heterocyclic compounds
including urazoles and 1,4-dihydropyridines. The process presented
here is operationally simple, environmentally benign, and
reactions have been mildly carried out in dichloromethane
at room temperature.
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Montmorillonite K-10: As a Useful Catalyst in Organic
Preparations
Bita Baghernejad
Montmorillonite K-10 has been used in many organic preparations
as a good solid catalyst. In this review, we wish to report
some applications of this catalyst in organic reactions.
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Animal Bone Meal (ABM): A Novel Natural Catalyst for
Thia-Michael Addition
Yassine Riadi, Rachid Mamouni, Younes Abrouki,
Mohammadine El Haddad, Nabil Saffaj, Said El Antri, Sylvain
Routier, Gérald Guillaumet and Said Lazar
The preparation and use of Animal Bone Meal (ABM) as
natural catalyst is described for C-S bond formation by thia-Michael
addition. This new natural heterogeneous method led to β-sulfinyl
adducts in very high yields after only a few minutes. Influence
of the thiol derivatives and substitution on chalcones is
discussed.
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