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Letters in Organic Chemistry
ISSN: 1570-1786
Letters in Organic Chemistry
Volume 5, Number 1, January 2008
Contents
One-Pot Synthesis of Norfloxacin Ethyl Ester from
3 Chloro-4-Fluoroaniline in Ionic Liquid
Pp.1-2
Shengdong Zhu, Yuanxin Wu, Ziniu Yu, Xizhou Shen, Chengmiao
Xu, Jun Yao, Hong Huang and Shiwei Jin
[Abstract]
Synthesis and Antibacterial Activity of New (2,3-dioxo
indolin-1-yl)acetamides Pp. 3-7
R. Bouhfid, N. Joly, F. Ohmani, E.M. Essassi, V. Lequart,
J. Banoub, K. Kheddid, R. Charof, M. Massoui and P. Martin
[Abstract]
A New Methodology to Prepare 2-Halogenoimidazoles
via a N-THP Protection Pp. 8-10
Nicolas Primas, Alexandre Bouillon, Jean-Charles Lancelot,
Jana Sopkova-de Oliveira Santos, Jean-François Lohier
an Sylvain Rault
[Abstract]
A New Application for PyOX-Ligands: The Asymmetri
Henry Reaction Pp. 11-16
Markku J. Oila, Jan E. Tois and Ari M.P. Koskinen
[Abstract]
Steroidal δ-Alkenyl
Oximes as Ambident Nucleophiles: Electrophile-Induced Formation
of Oxazepane Derivatives in the Bis-Estrone Series
Pp. 17-21
Erzsébet Mernyák, Zsolt Bikádi, Eszter
Hazai, László Márk Gyula Schneider and
János Wölfling
[Abstract]
Unexpected Opening of the Benzodiazepine Ring
During Acetylation Pp. 22-25
Constantinos Neochoritis, Minodora Pozarentzi, Julia Stephanidou-Stephanatou
and Constantinos A. Tsoleridis
[Abstract]
Copper(I) Bromide Promoted Selective Reduction
of N substituted Phthalimides with Zinc
Pp. 26-29
Jiyu Wang, Fan Yang, Jianfeng Shen, Wen Wang and Lixi
Wang
[Abstract]
Bismuth(III) Triflate-Catalyzed Dehydrative Glycosidation
Using 1-Hydroxy Sugars Pp. 30-33
Takashi Yamanoi, Ryo Inoue, Sho Matsuda and Keita Hamasaki
[Abstract]
Zr(OTf)4-Catalyzed
Direct Three-Component Mannich-Type Reaction of Carbamates:
An Efficient One-Step Synthesis of N-Protected
β-
Aryl-β-Amino
Ketones Pp. 34-37
Lei Yang, Li-Wen Xu, Wei Sun and Chun-Gu Xia
[Abstract]
First Tetrakis-Srn1
Reaction in Naphthoquinone Series Pp. 38-41
Abdelouahab Beziane, Omar Khoumeri, Thierry Terme and
Patrice Vanelle
[Abstract]
Hydrazyl-Nitrones and Hydrazyl-Nitroxides,Multifunctional
Molecules as Sensors and Probes
Pp. 42-46
Petre Ionita
[Abstract]
A Convenient Synthesis of Quinolines via
Ionic Liquid Catalysed Friedländer Annulation
Pp. 47-50
Tao Zhou, Jian-Li Lin and Zhen-Chu Chen
[Abstract]
A Convenient, Solvent Free and High Yielding Synthesis
of Bicyclo-Heterocyclic Compounds Pp. 51-54
Sham M. Sondhi and Reshma Rani
[Abstract]
Phosphine-Catalysed [3+2] Cycloaddition of Ethyl
Buta 2,3-Dienoate and 4-Quinolone-1,3-Dicarboxylate
Pp. 55-56
Yaseen A. Al-Soud, Najim A. Al-Masoudi, Thomas Hass and
Uwe Beifuß
[Abstract]
An Intriguing, Regioselective Synthesis of Novel
2-(1 Adamantylmethyl) tetrahydropyridines Pp. 57-59
Ioannis Papanastasiou, George B. Foscolos and Andrew Tsotinis
[Abstract]
A Facile Synthesis of Polyhydroquinoline Derivatives
via the Hantzsch Reaction Under Solvent Free-Conditions
Using Potassium Dodecatungsto Cobaltate Trihydrate (K5CoW12O40.3H2O)
Pp. 60-64
Lingaiah Nagarapu, Satyender Apuri, Subhashini Gaddam,
Rajashaker Bantu, Venu C. Mahankhali and Srinivas Kantevari
[Abstract]
Solvent-Free Mechanochemical Reaction of [60]Fullerene
with Phenylhydrazine Hydrochlorides Pp. 65-68
Zhong-Xiu Chen, Bo Zhu and Guan-Wu Wang
[Abstract]
Chemoenzymatic Synthesis of the Aggregation Pheromones
(S)-2-methyl-4-octanol and (4S, 2E)-6-methyl
2-hepten-4-ol Pp. 69-72
Francisco A. Marques, Ademir Zimmermann, Carlos E. Dela
and Beatriz H.L.N.S. Maia
[Abstract]
Abstracts
[Back to top]
One-Pot Synthesis of Norfloxacin Ethyl Ester
from 3 Chloro-4-Fluoroaniline in Ionic Liquid
Shengdong Zhu, Yuanxin Wu, Ziniu Yu, Xizhou Shen, Chengmiao
Xu, Jun Yao, Hong Huang and Shiwei Jin
Norfloxacin ethyl ester was prepared from 3-chloro-4-fluoroaniline
in ionic liquid in a one-pot procedure by condensation with
EMME [ethoxymethylenemalonic diethyl ester], cyclization,
ethylation and condensation with anhydrous piperazine. After
its hydrolysis, norfloxacin was obtained with an overall yield
of 72.7%.
[Back to top]
Synthesis and Antibacterial Activity of New (2,3-dioxo
indolin-1-yl)acetamides
R. Bouhfid, N. Joly, F. Ohmani, E.M. Essassi, V. Lequart,
J. Banoub, K. Kheddid, R. Charof, M. Massoui and P. Martin
The synthesis of a novel series of isatin derivatives
bearing an acetamide group is described. These 2-(2,3-dioxo-indolin-1-yl)acetamide
derivatives were synthesized by N-carboxymethylation
of isatin followed by conversion of the carboxylic acid function
into a tertiary amide. In a preliminary study, this series
of compounds were tested in vitro for their biological
activity, against various strains of bacteria
[Back to top]
A New Methodology to Prepare 2-Halogenoimidazoles
via a N-THP Protection
Nicolas Primas, Alexandre Bouillon, Jean-Charles Lancelot,
Jana Sopkova-de Oliveira Santos, Jean-François Lohier
and Sylvain Rault
A straightforward access to 2-halogenoimidazoles via
a N-THP protection was described in this paper. The
N-THP protecting group is easily introduced by reaction
of 2-chloro-THP with imidazole. Lithiation followed by reaction
with an appropriate electrophile affords 2-halogeno N-THP
derivatives. The THP protecting group is then cleaved to get
the title compounds in good to high yields.
[Back to top]
A New Application for PyOX-Ligands: The Asymmetric
Henry Reaction
Markku J. Oila, Jan E. Tois and Ari M.P. Koskinen
C2-dissymmetric PyOX-ligands
have been applied to the asymmetric Henry reaction. This widely
applicable reaction is easy to perform, requires no inert
atmospheres or dry solvents, and gives good selectivities.
By adjusting ligand side-chains, a significant impact on selectivities
was observed.
[Back to top]
Steroidal δ-Alkenyl
Oximes as Ambident Nucleophiles: Electrophile-Induced Formation
of Oxazepane Derivatives in the Bis-Estrone Series
Erzsébet Mernyák, Zsolt Bikádi, Eszter
Hazai, László Márk, Gyula Schneider and
János Wölfling
Electrophile-induced cyclization of steroidal δ-alkenyl
oximes and oxime ethers and subsequent hydride reduction of
the cyclic nitrones led to new halogenated or selenylated
N-hydroxy- or N-benzyloxy-aza-D-homo-estrones. Starting
from a 13β-D-secoestrone
oxime or oxime ether, steroidal dimers were isolated in intermolecular
1,3-dipolar cycloaddition of the cyclic nitrone to the C=N
double bond of the oxazepine intermediates.
[Back to top]
Unexpected Opening of the Benzodiazepine Ring
During Acetylation
Constantinos Neochoritis, Minodora Pozarentzi, Julia Stephanidou-Stephanatou
and Constantinos A. Tsoleridis
Reaction of 2,4-diaryl-2,3-dihydro-1H-1,5-benzodiazepines
1 either with acetyl chloride in dry CH2Cl2
in the presence of pyridine, or with acetic anhydride in the
presence or absence of base afforded, after unexpected opening
of the benzodi-azepine ring, N-butenylidene-amino-phenylacetamides
3 in excellent yields instead of the expected ring tautomers
2.
[Back to top]
Copper(I) Bromide Promoted Selective Reduction of
N substituted Phthalimides with Zinc
Jiyu Wang, Fan Yang, Jianfeng Shen, Wen Wang and Lixin
Wang
A new selective reduction of N-substituted phthalimides
to the corresponding hydroxyl lactams is described. This reduction
performed smoothly under mild, concise and easily controllable
condition in good yield (up to 97%). The generality of the
reduction was also investigated and a wide range of substrates
were suitable for this reaction.
[Back to top]
Bismuth(III) Triflate-Catalyzed Dehydrative Glycosidation
Using 1-Hydroxy Sugars
Takashi Yamanoi, Ryo Inoue, Sho Matsuda and Keita Hamasaki
This paper describes the O-glycoside formation
from 1-hydroxy sugars by the bismuth(III) triflate-catalyzed
dehydrative glycosidation. The reactions of the 1-hydroxy
sugars with some primary alcohols in the presence of only
5 mol% bismuth(III) triflate at reflux for 15 min in dichloromethane
afforded the O-glycosides in good yields. This paper
clarifies several important properties during the bismuth(III)
triflate-catalyzed dehydrative glycosidation using 1-hydroxy
sugars.
[Back to top]
Zr(OTf)4-Catalyzed
Direct Three-Component Mannich-Type Reaction of Carbamates:
An Efficient One-Step Synthesis of N-Protected
β-
Aryl-β-Amino
Ketones
Lei Yang, Li-Wen Xu, Wei Sun and Chun-Gu Xia
Carbamates were reacted in one pot with aromatic aldehyde
and ketones at ambient temperature in the presence of catalytic
amount of Zr(OTf)4 to furnish
the corresponding N-protected β-amino-β-aryl
ketones in good yields.
[Back to top]
First Tetrakis-Srn1
Reaction in Naphthoquinone Series
Abdelouahab Beziane, Omar Khoumeri, Thierry Terme and
Patrice Vanelle
A series of highly functionalized naphthoquinones was
prepared by an original tetrakis-Srn1
reaction involving 2,3,6,7-tetrakis(chloromethyl)-5,8-dimethoxynaphthalene-1,4-dione
with various nitronate anions and S-centered anions.
[Back to top]
Hydrazyl-Nitrones and Hydrazyl-Nitroxides,Multifunctional
Molecules as Sensors and Probes
Petre Ionita
Several compounds containing in the same molecule a hydrazyl
moiety and a nitrone (or a nitroxide moiety) were characterised
by different means, as visible spectroscopy, hydrophobicity,
cyclic voltammetry, bond dissociation energy (BDE), electron
paramagnetic resonance spectroscopy (EPR), and pKa
values, in order to evaluate them as sensors and probes for
monitoring acid-base, redox, and free radical processes.
[Back to top]
A Convenient Synthesis of Quinolines via
Ionic Liquid Catalysed Friedländer Annulation
Tao Zhou, Jian-Li Lin and Zhen-Chu Chen
A convenient and green protocol for the synthesis of
quinolines by Friedländer annulation using an acidic
ionic liquid, ethylammonium nitrate, as both a catalyst and
a reaction medium is reported. The reactions were performed
at 450 C with moderate to
excellent yields. The recovered ionic liquid could be reused
for several cycles without any loss of activity.
[Back to top]
A Convenient, Solvent Free and High Yielding Synthesis
of Bicyclo-Heterocyclic Compounds
Sham M. Sondhi and Reshma Rani
A variety of bicyclo-heterocyclic compounds have been
synthesized by condensation of phthalic acid, homophathalic
acid, 1,2-phenylenediacetic acid, 2,3-pyridine dicarboxlic
acid, 3,4-pyridine dicarboxlic acid and 2,3-pyrazine dicarboxlic
acid with 1-(2-aminoethyl)-piperidine and furfuryl amine,
in one step using microwave irradiation technique. Bicyclo-heterocyclic
compounds were obtained within minutes in good chemical yields
and high purity.
[Back to top]
Phosphine-Catalysed [3+2] Cycloaddition of Ethyl Buta
2,3-Dienoate and 4-Quinolone-1,3-Dicarboxylate
Yaseen A. Al-Soud, Najim A. Al-Masoudi, Thomas Hass and
Uwe Beifuß
Phosphine-catalysed [3+2] cycloaddition of ethyl buta-2,3-dienoate
and 4-quinolone-1,3-dicarboxylate furnished the (3aS,9aR)-triethyl
9-oxo-9,9a-dihydro-1H-cyclopenta[b]quinoline-3,4,9a(3aH)-tricarboxylate.
[Back to top]
An Intriguing, Regioselective Synthesis of Novel 2-(1
Adamantylmethyl) tetrahydropyridines
Ioannis Papanastasiou, George B. Foscolos and Andrew Tsotinis
Treatment of piperidine 8 with acetyl chloride
or ethyl chloroformate in the presence of triethylamine gave
the 2,3-dehydrogenated products 10a and 10b,
respectively, together with the expected N-acylpiperidines
9.
[Back to top]
A Facile Synthesis of Polyhydroquinoline Derivatives
via the Hantzsch Reaction Under Solvent Free-Conditions
Using Potassium Dodecatungsto Cobaltate Trihydrate (K5CoW12O40.3H2O)
Lingaiah Nagarapu, Satyender Apuri, Subhashini Gaddam,
Rajashaker Bantu, Venu C. Mahankhali and Srinivas Kantevari
A facile and efficient one-pot synthesis of polyhydroquinoline
derivatives via the Hantzsch reaction using a variety of aldehydes,
5,5-dimethyl-1,3-cyclohexanedione or 1,3-cyclohexanedione,
ethyl acetoacetate, and ammonium acetate in the presence of
potassium dodecatungstocobaltate trihydrate [K5CoW12O40.
3H2O] as a heterogeneous
catalyst in a solvent-free media at 900
C is described herein . The present methodology
offers several advantages such as excellent yields, simple
procedure, shorter reaction times (10-25 min.), milder conditions
and the catalyst exhibited remarkable reusability.
[Back to top]
Solvent-Free Mechanochemical Reaction of [60]Fullerene
with Phenylhydrazine Hydrochlorides
Zhong-Xiu Chen, Bo Zhu and Guan-Wu Wang
The solvent-free reaction of [60]fullerene with phenylhydrazine
hydrochlorides 1a-e in the presence of sodium
carbonate under high-speed vibration milling conditions afforded
1-aryl-1,2-dihydro[60]fullerenes 2a-e, amongst
them 1-(4-nitrophenyl)-1,2-dihydro[60]fullerene 2e
could not be obtained in the liquid-phase reaction. When excess
sodium nitrite was employed to replace sodium carbonate, fullerotriazoline
3 was formed. Product 3 tended to decompose
via the loss of molecular nitrogen to give azafulleriod 4.
[Back to top]
Chemoenzymatic Synthesis of the Aggregation Pheromones
(S)-2-methyl-4-octanol and (4S, 2E)-6-methyl
2-hepten-4-ol
Francisco A. Marques, Ademir Zimmermann, Carlos E. Delay
and Beatriz H.L.N.S. Maia
In this work we synthesized the aggregation pheromones
(S)-2-methyl-4-octanol and (4S, 2E)-6-methyl-2-hepten-4-ol
in high enantiomeric excess applying as the key step an enzymatic
resolution of 5-methyl-1-hexyn-3-ol.
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