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Letters in Organic Chemistry
ISSN: 1570-1786
Letters in Organic Chemistry
Volume 5, Number 7, October 2008
Contents
Facile Synthesis of Anticancer Drug NCX 4040 in Mild
Conditions Pp. 510-513
Mei Xiao, Hongsong Yang, Suzane M. Klein,
Christian M. Muenyi, William L. Stone and Yu L. Jiang
[Abstract] [Purchase
Article]
Facile Synthesis of the Sex Pheromone
Components of the Legume Pod Borer and Soybean Pod Borer by
Suzuki-Miyaura Cross-Coupling Reaction Pp.
514-517
Chen-Yu Wu, Min-Feng Hsien and Yao-Pin
Yen
[Abstract] [Purchase
Article]
Synthesis of 5-(Carbohydrate-ethynyl)-2'-deoxyuridine
Derivatives Pp. 518-521
Ruchun Yang, Haixin Ding, Yang Song, Weihong
Xiao, Qiang Xiao and Jun Wu
[Abstract] [Purchase
Article]
Synthesis of 6,13-Dithienylpentacenes
by Photolysis of their Endoperoxides Pp.
522-526
Katsuhiko Ono Takao Hiei, Mitsuhiro Tajika,
Keijiro Taga, Katsuhiro Saito, Masaaki Tomura, Jun-ichi Nishida
and Yoshiro Yamashita
[Abstract] [Purchase
Article]
Facile and Efficient Synthesis of Ethyl
3-Oxo-5-arylthiopentanoates, the Precursors for Nazarov Reagent
Pp. 527-529
H. Surya Prakash Rao Shaik Rafi and
K. Padmavathy
[Abstract] [Purchase
Article]
Synthesis of a New (+)-Catechin-Derived
Compound: 8 Vinylcatechin Pp. 530-536
Luís Cruz, Enrique Borges, Artur
M.S. Silva, Nuno Mateus and Victor de Freitas
[Abstract] [Purchase
Article]
Synthesis of a Thiophene Analog of Confusarine
Pp. 537-539
Jean-Jacques Youte and Roland Barret
[Abstract] [Purchase
Article]
A Novel Three-Component Reaction of
Dibenzylamine and an Aromatic Aldehyde with an Alkyl Isocyanide
in the Presence of Silica Gel: An Efficient Route for the
One-Pot Synthesis of Sterically Congested 2-(Dibenzylamino)-2-Aryl
Acetamide Derivatives Pp. 540-543
Ebrahim Ahmadi, Amir T. Mahyari, Ali Ramazani
and Mehdi N. Haghighi
[Abstract] [Purchase
Article]
QSAR and Docking Studies on Propenone
Derivatives as Dual COX and 5-LOX Inhibitors Pp.
544-554
Ponnurengam M. Sivakumar, Sethu K. Geetha
Babu, Vaibhav Sharma and Mukesh Doble
[Abstract] [Purchase
Article]
Supplemental
Data Pp. i-ii
Easy Electrochemical Synthesis of 2-amino-4-aryl-3-cyano-5-
ethoxycar-bonyl-6-methyl-4H-pyrans in the Absence
of Supporting Electrolyte Pp. 555-558
Giovanni Sotgiu
[Abstract] [Purchase
Article]
An Efficient Synthesis of 2,3-Diaryl-2-azabicyclooctanones
Via BiCl3-
Catalysed Three-Component aza Diels-Alder Reaction Pp.
559-562
Luis Astudillo S., Gabriel A. Vallejos,
Néstor Correa, Margarita Gutiérrez C., Walesca
de la Guarda and Vladimir V. Kouznetsov
[Abstract] [Purchase
Article]
A Novel Synthesis of p-Nitrobenzylphosphonic
Acid and its Action on Alkaline Phosphatase Pp.
563-565
James K. Hand, Amanda L. Stewart, Randy
B. Sears, Trianna R. McCall and Catherine M. Davis-McGibony
[Abstract] [Purchase
Article]
KAl(SO4)2.12H2O
Supported on Silica Gel Catalyzed Coupling of 4-Hydroxyproline
with Isatins, 11H-Indeno[1,2-b]quinoxalin-11-ones,
Quinones and 9H-Fluoren-9-one: An Efficient Synthesis
of Some Interesting Pyrroles Pp. 566-568
Ali R. Karimi and Ali A. Mohammadi
[Abstract] [Purchase
Article]
Novel Microwave-Assisted One-Pot Synthesis
of Heterocycle Phosphor Esters and Cyclic Oxophospholes with
Antibiotic Activity Pp. 569-575
Wafaa M. Abdou and Abeer A. Shaddy
[Abstract] [Purchase
Article]
Stereoselective Synthesis of 5-Thio-β-L-Fucopyranosyl
Phosphate Pp. 576-578
Tatsuo Miyazaki, Daisuke Hiyoshi, Masayuki Izumi, Hironobu
Hashimoto and Hideya Yuasa
[Abstract] [Purchase
Article]
An Efficient Synthesis of 7,11-diarylspiro[5.5]undecane-1,9-
dione by the Michael Condensation Under Ultrasound Irradiation
in Aqueous and Organic Two Phase in the Presence of Phase-Transfer
Catalyst Pp. 579-582
Ji-Tai Li, Xin-Li Zhai, Zhi-Ping Lin and
Xiao-Hui Zhang
[Abstract] [Purchase
Article]
Photochemical Degradation of Hyperforin
Pp. 583-586
Maurizio D’Auria, Lucia Emanuele and Rocco
Racioppi
[Abstract] [Purchase
Article]
Palladium-Catalyzed Cross-Couplings of
2-Tributylstannyl-N-Boc-2,3-dehydropiperidine, a
Cyclic Enecarbamate Pp. 587-590
Alessandro B. C. Simas, Daniel L. de Sales,
Samir F. A. Cavalcante, Cristina M. de Medeiros, Sandro H.S.
Moraes and Erika M. de Carvalho
[Abstract] [Purchase
Article]
ZnI2
Catalyzed Reduction of Ketones Under Solvent-Free Conditions
Pp. 591-593
Ling-Zhen Chen, Jia-Jian Peng, Jia-Yun Li, Ying
Bai, Ying-Qian Hu, Hua Yu Qiu, Hui Wu and Guo-Qiao
Lai
[Abstract] [Purchase
Article]
Minimizing Side Reactions in Classical Pyrazole
Synthesis from β-Oxonitriles:
The Use of Acetylhydrazine Pp. 594-598
Mikhail Krasavin and Igor O. Konstantinov
[Abstract] [Purchase
Article]
Microwave-Assisted Synthesis of 3-substituted
2 iminopyrido[2,3-e] [1,3] oxazin-4-ones Pp.
599-601
Thomas Kurz and Miriam K. Pein
[Abstract] [Purchase
Article]
Abstracts
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Article]
Facile Synthesis of Anticancer Drug NCX 4040 in Mild Conditions
Mei Xiao, Hongsong Yang, Suzane M. Klein,
Christian M. Muenyi, William L. Stone and Yu L. Jiang
A simple method is reported to synthesize an anticancer
drug, NCX 4040, conveniently in mild conditions using silicon
chemistry. A starting material, 4-hydroxybenzyl alcohol, was
silylated selectively first to give t-butyldimethylsilyl
4-hydroxybenzyl ether, which was then converted to NCX 4040
by esterification, desilylation, hydrochlorination and nitration.
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Article]
Facile Synthesis of the Sex Pheromone Components of the Legume
Pod Borer and Soybean Pod Borer by Suzuki-Miyaura Cross-Coupling
Reaction
Chen-Yu Wu, Min-Feng Hsien and Yao-Pin
Yen
The pheromone components of the legume pod borer, (E,E)-10,12-hexadecadienal,
and the soybean pod borer, (E,E)-8,10-dodecadienyl
acetate, were synthesized in good yields via Suzuki-Miyaura
cross-coupling reactions.
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Article]
Synthesis of 5-(Carbohydrate-ethynyl)-2'-deoxyuridine Derivatives
Ruchun Yang, Haixin Ding, Yang Song, Weihong
Xiao, Qiang Xiao and Jun Wu
Sonogashira reaction has been successfully applied to
the synthesis of a series of 5-(carbohydrate-ethynyl)-2'-deoxyuridines
for the first time. The synthetic route is general, high-yielding
and compatible with the readily removable protecting group.
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Article]
Synthesis of 6,13-Dithienylpentacenes by Photolysis of their
Endoperoxides
Katsuhiko Ono Takao Hiei, Mitsuhiro Tajika,
Keijiro Taga, Katsuhiro Saito, Masaaki Tomura, Jun-ichi Nishida
and Yoshiro Yamashita
The exposure of solutions of 6,13-dithienylpentacenes
to sunlight in air afforded their endoperoxides. The solutions
and thin films of the endoperoxides were irradiated with UV
light to reproduce the 6,13-dithienylpentacenes. These conversions
are of interest as an ecological film-formation technology
in the study of organic semiconductors.
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Article]
Facile and Efficient Synthesis of Ethyl 3-Oxo-5-arylthiopentanoates,
the Precursors for Nazarov Reagent
H. Surya Prakash Rao Shaik Rafi and
K. Padmavathy
A facile, efficient and high-yielding two-step synthesis
of 3-oxo-5-arylthiopentanoates - the precursors for Nazarov
reagent - from low-cost bench top chemicals like thiophenols,
acrylonitrile, zinc and ethyl bromoacetate via the
Blaise reaction, is reported.
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Article]
Synthesis of a New (+)-Catechin-Derived Compound: 8 Vinylcatechin
Luís Cruz, Enrique Borges, Artur
M.S. Silva, Nuno Mateus and Victor de Freitas
A strategy for the synthesis of 8-vinylcatechin was developed,
which involves (+)-catechin silylation with TBDMS-Cl, followed
by bromination with NBS, a cross-coupling Suzuki reaction
with vinylboronic acid pinacol ester and cleavage of TBDMS
groups with TBAF, affording the 8-vinylcatechin.
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Article]
Synthesis of a Thiophene Analog of Confusarine
Jean-Jacques Youte and Roland Barret
A new thiophene analog of confusarine was synthesized
by the use of Wittig reaction and radical cyclisation or photocyclisation.
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Article]
A Novel Three-Component Reaction of Dibenzylamine and an Aromatic
Aldehyde with an Alkyl Isocyanide in the Presence of Silica Gel: An Efficient Route for the One-Pot Synthesis of Sterically Congested 2-(Dibenzylamino)-2-Aryl Acetamide
Derivatives
Ebrahim Ahmadi, Amir T. Mahyari, Ali Ramazani
and Mehdi N. Haghighi
Addition of an isocyanide to an iminium ion intermediate
that forms from the reaction between an aromatic aldehyde
and dibenzylamine, leads to formation of sterically congested
2-(dibenzylamino)-2-aryl acetamide derivatives in the presence
of silica gel powder.
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Article]
QSAR and Docking Studies on Propenone Derivatives as Dual
COX and 5-LOX Inhibitors
Ponnurengam M. Sivakumar, Sethu K. Geetha
Babu, Vaibhav Sharma and Mukesh Doble
Quantitative structure activity relationships were developed
for seventeen propenone derivatives reported in the literature
that act as dual COX and 5-LOX inhibitors. Predominantly spatial,
thermodynamic, topological, and electronic descriptors appear
in the models. Docking between these compounds and COX-1,
COX-2 and 5-LOX enzymes was also performed and mathematical
relationships were developed between the binding energy and
activity.
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Article]
Easy Electrochemical Synthesis of 2-amino-4-aryl-3-cyano-5-
ethoxycar-bonyl-6-methyl-4H-pyrans in the Absence
of Supporting Electrolyte
Giovanni Sotgiu
An easy electrochemical synthesis of 2-amino-4-aryl-3-cyano-5-ethoxycarbonyl-6-methyl-4H-pyrans
has been set up, by galvanostatic electrolysis of a mixture
of arylidenemalononitrile and ethyl acetoacetate in the absence
of supporting electrolyte. Very high yields are obtained by
a particularly simple procedure.
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Article]
An Efficient Synthesis of 2,3-Diaryl-2-azabicyclooctanones
Via BiCl3-
Catalysed Three-Component aza Diels-Alder Reaction
Luis Astudillo S., Gabriel A. Vallejos,
Néstor Correa, Margarita Gutiérrez C., Walesca
de la Guarda and Vladimir V. Kouznetsov
The first three-component coupling reactions between
various anilines (1), benzaldehydes (2),
and cyclohexen-2-one (3) were performed under
mild conditions (acetonitrile, room temperature, 14 h) in
the presence of 20 mol % BiCl3
to obtain new 2,3-diaryl-2-aza[2.2.2]octan-5-ones (4,5)
with interesting acetylcholinesterase inhibitory properties.
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A Novel Synthesis of p-Nitrobenzylphosphonic Acid
and its Action on Alkaline Phosphatase
James K. Hand, Amanda L. Stewart, Randy
B. Sears, Trianna R. McCall and Catherine M. Davis-McGibony
p-Nitrobenzylphosphonic acid was obtained via
a nucleophilic substitution of nitrobenzyl bromide with trimethyl
phosphite as opposed to nitration of benzylphosphonic acid.
This compound is a competitive inhibitor of alkaline phosphatase
(KI ~ 125 μM)
and has potential to inhibit a wide range of other phosphatases
including serine/threonine phosphatases and tyrosine phosphatases.
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KAl(SO4)2.12H2O
Supported on Silica Gel Catalyzed Coupling of 4-Hydroxyproline
with Isatins, 11H-Indeno[1,2-b]quinoxalin-11-ones,
Quinones and 9H-Fluoren-9-one: An Efficient Synthesis
of Some Interesting Pyrroles
Ali R. Karimi and Ali A. Mohammadi
Some interesting pyrrole derivatives were synthesized
in moderate to high yields by coupling of 4-hydroxyproline
with isatins, 11H-indeno[1,2-b]quinoxalin-11-ones,
quinones and 9H-fluoren-9-one, in the presence of
catalytic amount of Alum supported on silica gel (Alum-SiO2),
under microwave irradiation.
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Article]
Novel Microwave-Assisted One-Pot Synthesis of Heterocycle
Phosphor Esters and Cyclic Oxophospholes with Antibiotic Activity
Wafaa M. Abdou and Abeer A. Shaddy
Reactions of 5,6-di-(2`-furyl)-3-oxo-2,3-dihydropyridazin-4-carbonitrile
(1) with Wittig-Horner reagents were investigated
under microwave irradiation, and the effect of basic catalysis.
The methodology afforded moderate to high yields of fused
heterocycles bearing a phosphonate ester and / or phosphor-containing
fused heterocycles. Bioassay results showed that the antibiotic
activity of the new synthesized phosphorus compounds is significantly
high when compared to available Streptomycin and Mycostatin
(standard).
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Stereoselective Synthesis of 5-Thio-β-L-Fucopyranosyl
Phosphate
Tatsuo Miyazaki, Daisuke Hiyoshi, Masayuki
Izumi, Hironobu Hashimoto and Hideya Yuasa
The fucosyltransferase-catalyzed 5-thiofucosylation reaction
suffered from limitations in the β-selective
synthesis of GDP-5-thiofucose, a donor substrate. We found
that the use of electronegatively-substituted benzoate groups
for 5-thiofucose protection improved the β-selectivity
in the phosphorylation step. We thus achieved the synthesis
of 5-thio-β-L-fucosyl
phosphate in 50% yield from 5-thiofucose, using the 3,5-dinitrobenzoyl
group.
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An Efficient Synthesis of 7,11-diarylspiro[5.5]undecane-1,9-
dione by the Michael Condensation Under Ultrasound Irradiation
in Aqueous and Organic Two Phase in the Presence of Phase-Transfer
Catalyst
Ji-Tai Li, Xin-Li Zhai, Zhi-Ping Lin and
Xiao-Hui Zhang
Improved synthesis of 7,11-diarylspiro[5.5]undecane-1,9-dione
via double Michael condensation of 1,5-bisaryl-1,4-pentadien-3-one
with cyclohexanone was carried out in 51-96% yields for 3-12
h in CH2Cl2-H2O
in the presence of phase-transfer catalyst under ultrasound
irradiation. In comparison with reported methods, the main
advantages of the present procedure are shorter reaction time
and higher yields.
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Photochemical Degradation of Hyperforin
Maurizio D’Auria, Lucia Emanuele and Rocco
Racioppi
Irradiation of hyperforin in acetonitrile gave a single
degradation product with a first order kinetics (k
= 3.23 M h-1). The degradation
product was a 1:1 tautomeric mixture of 2-methyl-3-hydroxy-4-(1-oxo-2-methyl-1-propyl)-1,5-dioxo-6-(3methyl-1-but-2-enyl)-2-cyclohexene
and 2-methyl-1,3,5-trioxo-4-(1-hydroxy-2-methyl-1-propylene)-6-(3-methyl-1-but-2-enyl)-cyclohexane.
The product can also be obtained through three Norrish II
reactions, followed by a fragmentation reaction.
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Palladium-Catalyzed Cross-Couplings of 2-Tributylstannyl-N-Boc-2,3-
dehydropiperidine, a Cyclic Enecarbamate
Alessandro B. C. Simas, Daniel L. de Sales,
Samir F. A. Cavalcante, Cristina M. de Medeiros, Sandro H.S.
Moraes and Erika M. de Carvalho
Cross-couplings of 2-tributylstannyl-N-Boc-2,3-dehydropiperidine,
a six-membered cyclic enecarbamate, with aryl iodides and
triflates are reported for the first time. Under the Pd(0)/AsPh3
catalytic system (Farina´s conditions), better conversions
of this challenging substrate into the expected products were
achieved with shorter reactions carried out under higher temperature.
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ZnI2 Catalyzed Reduction
of Ketones Under Solvent-Free Conditions
Ling-Zhen hen, Jia-Jian Peng, Jia-Yun Li, Ying
Bai, Ying-Qian Hu, Hua Yu Qiu, Hui Wu and Guo-Qiao
Lai
The Zn-promoted direct reduction of ketones into the
corresponding alcohols with silane under solvent-free conditions
was reported. With ZnI2 as
a catalyst, hydrosilylation of a large variety of ketones
with silanes could proceed smoothly in the air, and exhibit
excellent rates and high conversions.
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Minimizing Side Reactions in Classical Pyrazole Synthesis
from β-Oxonitriles:
The Use of Acetylhydrazine
Mikhail Krasavin and Igor O. Konstantinov
A new two-step, one-pot alternative protocol for preparation
of 1H-pyrazole-5-amines from 3-oxoalkanenitriles
utilizing readily available acetylhydrazine has been developed.
Typical by-products formed in traditional reactions of 3-oxoalkanenitriles
with hydrazine are not formed when the present method is used,
thus facilitating purification on a large scale. The method
was used to prepare a medicinally important heterocycle on
a kilogram scale.
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Microwave-Assisted Synthesis of 3-substituted
2 iminopyrido[2,3-e] [1,3] oxazin-4-ones
Thomas Kurz and Miriam K. Pein
The rapid microwave-assisted preparation of 3-substituted
2-imino-pyrido[2,3-e][1,3]oxazin-4-ones starting
from N-aralkoxy-3-hydroxy-pyridine-2-carboxamides, 3-hydroxy-pyridine-2-carboxamides
or 3 hydroxy-pyridine-2-carboxylic acid hydrazides and cyanogen
bromide is described.
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