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Letters in Organic Chemistry
ISSN: 1570-1786
Letters in Organic Chemistry
Volume 7, Number 4, June 2010
Contents
Graphical
Abstracts Pp. i-v
Triethylamine Promoted Efficient Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones/thiones
Using a Solvent-Free Biginelli Condensation Pp. 272-276
Abdelmadjid Debache, Wassima Ghalem, Raouf
Boulcina, Ali Belfaitah, Salah Rhouati and Bertrand
Carboni
[Abstract] [Purchase
Article]
A Novel Biginelli-Like Reaction: An Efficient One-pot
Synthesis of Spiro[oxindole-quinazoline/pyrimidine]ones
Pp. 277-282
Hassan Kefayati, Kurosh Rad-Moghadam, Masoumeh
Zamani and Sanaz Hosseyni
[Abstract] [Purchase
Article]
Synthesis and Conformational Analysis of the First
3-Oxa-7-thia-1-r-azabicyclo[3.3.0]-c-5-octane
Single Functionalised at the C-5 Position Pp. 283-290
Andrada But, Pedro Lameiras, Ioan Silaghi-Dumitrescu,
Carmen Batiu, Sophie Guillard, Yvan Ramondenc and
Mircea Darabantu
[Abstract] [Purchase
Article]
Editor’s
Choice
Reactions of 4-(Diethylamino)selenet-2(2H)-imine
with Nucleophiles – Synthesis of 2-Methylen-3-oxobutane
Selenoamides Pp. 291-297
Plamen K. Atanassov, Anthony Linden and
Heinz Heimgartner
[Abstract] [Purchase
Article]
One-Pot Three-Component Solvent-Free Syntheses of
n-Alkyl-Bridged N,N,N’,N’-tetra(2-hydroxybenzyl)diamines
and N,N-bis(2-hydroxybenzyl) amines Pp.
298-305
Antti Riisiö, Oula Wichmann and
Reijo Sillanpää
[Abstract] [Supplementary
Material] [Purchase
Article]
Ceric Ammonium Nitrate: An Efficient Catalyst for
One-Pot Synthesis of 2,2,4-Trimethyl-1,2-dihydroquinolines
Pp. 306-310
Shylaprasad Durgadas, Vijay K. Chatare,
Khagga Mukkanti and Sarbani Pal
[Abstract] [Purchase
Article]
One-Pot Pictet-Spengler Reaction and Esterification
for the Preparation of a Key Tadalafil Synthetic Intermediate
Pp. 311-313
Dina Scarpi, Ernesto G. Occhiato, Antonio
Guarna and Valerio Borzatta
[Abstract] [Purchase
Article]
Diphenylammonium Triflate: A Novel and Efficient Catalyst
for Synthesis of Spiro-Heterocyclic Compounds Pp.
314-318
Jianjun Li, Jian Sun and Weike
Su
[Abstract] [Purchase
Article]
Synthesis of Imides and Amides from Diacetyl-L-Tartaric
Acid Anhydride Pp. 319-322
Sara Naz, Javid H. Zaidi, Tahir Mehmood,
Sher Wali, Muhammad Ali, Muhammad Taha and Khalid
M. Khan
[Abstract] [Purchase
Article]
An Efficient Synthesis of 1,5-Diaryl-1,4-pentadien-3-one
Oxime in the Presence of Anhydrous Sodium Sulfate
Pp. 323-326
Ji-Tai Li, Xin-Li Zhai, Bo Bai and
Yan-Hua Liang
[Abstract] [Purchase
Article]
Synthesis and In Vitro Evaluation of New
Tacrine Derivates-Bis- Alkylene Linked 7-MEOTA Pp.
327-331
Jan Korabecny, Ondrej Holas, Kamil Musilek,
Miroslav Pohanka, Veronika Opletalova, Vlastimil Dohnal and
Kamil Kuca
[Abstract] [Purchase
Article]
Novel Synthesis of 3-Arylated 5,6-Dimethoxybenzo[d]isothiazole
1,1-Dioxides Pp. 332-334
Fei Xie, Bing-Lei Gao, De-Feng Wang and
Zhao-Peng Liu
[Abstract] [Purchase
Article]
Synthesis of the α-Tocopheramine-15N
Model Compound 2,2,5,7,8- Pentamethyl-6-chromanylamine-15N
Pp. 335-337
Stefan Böhmdorfer, Lars Gille and
Thomas Rosenau
[Abstract] [Purchase
Article]
Antiradical Activity of β-Ionyl
Compounds Pp. 338-342
Anil K. Singh and Solomon B. Libsu
[Abstract] [Purchase
Article]
Chiral Ionic Liquid Mediated Diels-Alder Reaction
Between Anthrone Enolate and Maleimides Pp. 343-347
Nitin A. Mirgane, Mohammed H.H. Akhtar and
Anil V. Karnik
[Abstract] [Purchase
Article]
Abstracts
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Article]
Triethylamine Promoted Efficient Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones/thiones
Using a Solvent-Free Biginelli Condensation
Abdelmadjid Debache, Wassima Ghalem, Raouf
Boulcina, Ali Belfaitah, Salah Rhouati and Bertrand
Carboni
An efficient and simple protocol has been developed for
the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones
by a one-pot three-component cyclocondensation reaction of
an aromatic aldehyde, β-ketoester,
and urea or thiourea under solvent-free conditions using triethylamine
(Et3N) as catalyst for the
Biginelli reaction.
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Article]
A Novel Biginelli-Like Reaction: An Efficient One-pot
Synthesis of Spiro[oxindole-quinazoline/pyrimidine]ones
Hassan Kefayati, Kurosh Rad-Moghadam, Masoumeh
Zamani and Sanaz Hosseyni
Some new spiro[oxindole-quinazoline/pyrimidine]ones were synthesized
via a novel three-component Biginelli-like reaction
between isatin, cyclic or acyclic 1,3-dicarbonyl compounds,
and urea, N-methyl urea or thiourea in one pot and
good yields.
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Article]
Synthesis and Conformational Analysis of the First
3-Oxa-7-thia-1-r-azabicyclo[3.3.0]-c-5-octane
Single Functionalised at the C-5 Position
Andrada But, Pedro Lameiras, Ioan Silaghi-Dumitrescu,
Carmen Batiu, Sophie Guillard, Yvan Ramondenc and
Mircea Darabantu
Starting from TRIS [2-amino-2-(hydroxymethyl)propane-1,3-diol]
via its thia analogue, 2-amino-2-(mercaptomethyl)propane-1,3-diol’
double cyclocondensation with formaldehyde, we report a four
steps synthesis of the first term in the title series of compounds,
bearing the exploitable hydroxymethyl functionality at the
C-5 position. Conformational analysis is discussed based on
DFT calculations and 1H-DNMR.
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Article]
Reactions of 4-(Diethylamino)selenet-2(2H)-imine
with Nucleophiles – Synthesis of 2-Methylen-3-oxobutane
Selenoamides
Plamen K. Atanassov, Anthony Linden and
Heinz Heimgartner
3-Acetyl-N-(4-bromophenyl)-4-(diethylamino)selenet-2(2H)-imine
(5a), which is conveniently obtained from
the formal [2+2] cycloaddition of 4-bromophenyl isoselenocyanate
and 4-(diethylamino)-3-butyn-2-one, reacts with amines, alcohols,
water, and thiophenol to give the corresponding 2-methylen-3-oxobutane
selenoamides 7 in good yields via
ring opening to the ketenimine 6 and subsequent
addition of the nucleophile.
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Article]
One-Pot Three-Component Solvent-Free Syntheses of
n-Alkyl-Bridged N,N,N’,N’-tetra(2-hydroxybenzyl)diamines
and N,N-bis(2-hydroxybenzyl) amines
Antti Riisiö, Oula Wichmann and
Reijo Sillanpää
[Supplementary
Material]
A simple solvent-free method to prepare four N,N,N’,N’-tetra(2-hydroxy-3,5-dimethylbenzyl)diaminoalkanes
and four N,N,N’,N’-tetra(2-hydroxy-5-t-butyl-3-methylbenzyl)-diaminoalkanes
containing a long n-alkyl-bridge (5-8 CH2
groups between N-atoms) is described. In addition, preparations
of four dihydrochlorides of prepared n-alkyl-bridged
N,N,N’,N’-tetra(2-hydroxybenzyl)diamines
are described. This method was also tested in the preparation
of eight previously reported N,N-bis(2-hydroxybenzyl)amine
derivatives.
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Article]
Ceric Ammonium Nitrate: An Efficient Catalyst for
One-Pot Synthesis of 2,2,4-Trimethyl-1,2-dihydroquinolines
Shylaprasad Durgadas, Vijay K. Chatare,
Khagga Mukkanti and Sarbani Pal
Ceric ammonium nitrate (CAN) catalyzed the one-pot synthesis
of 2,2,4-trimethyl-1,2-dihydroquinoline derivatives from substituted
anilines and acetone via a modified Skraup reaction.
The methodology was used to synthesize a novel dihydroquinoline-based
compound derived from an anti-inflammatory agent nimesulide.
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Article]
One-Pot Pictet-Spengler Reaction and Esterification
for the Preparation of a Key Tadalafil Synthetic Intermediate
Dina Scarpi, Ernesto G. Occhiato, Antonio
Guarna and Valerio Borzatta
A new method is reported for the preparation of 2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic
acid methyl ester, a key intermediate in the synthesis of
Tadalafil which is used for the treatment of male erectile
dysfunction, via one-pot esterification and Pictet-Spengler
reaction.
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Article]
Diphenylammonium Triflate: A Novel and Efficient Catalyst
for Synthesis of Spiro-Heterocyclic Compounds
Jianjun Li, Jian Sun and Weike Su
A general and practical one-pot synthesis of spiro-heterocyclic
compounds using diphenylammonium triflate (DPAT, 5 mol%) as
a novel and efficient catalyst is described. The pseudo four-components
Biginelli-like reaction of 5,5-dimethyl-1,3-cyclohexanedione,
thiourea and aldehydes catalyzed by DPAT in refluxing ethanol
produced the corresponding spiro-heterocyclic compounds with
moderate to good yields. A possible mechanism is proposed.
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Synthesis of Imides and Amides from Diacetyl-L-Tartaric
Acid Anhydride
Sara Naz, Javid H. Zaidi, Tahir Mehmood,
Sher Wali, Muhammad Ali, Muhammad Taha and Khalid
M. Khan
Diacetyl-L-tartaric acid anhydride reacted with aromatic primary
amines to yield imides (3g-l) and amides
(4a-f). The ortho-substituted aromatic
primary amines either with electron donating or withdrawing
groups yielded amides, whereas para-substituted amines
produced imides. However, meta-substituted aromatic
primary amines with electron withdrawing residues afforded
amides while electron donating counterparts furnished imides.
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An Efficient Synthesis of 1,5-Diaryl-1,4-pentadien-3-one
Oxime in the Presence of Anhydrous Sodium Sulfate
Ji-Tai Li, Xin-Li Zhai, Bo Bai and
Yan-Hua Liang
A series of 1,5-diaryl-1,4-pentadien-3-one oximes were synthesized
via the reaction of 1,5-diaryl-1,4-pentadien-3-one
with hydroxylamine hydrochloride in the presence of anhydrous
sodium sulfate at refluxing EtOH to give good yields. This
method provided several advantages such as shorter reaction
time and higher yield.
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Article]
Synthesis and In Vitro Evaluation of New
Tacrine Derivates-Bis- Alkylene Linked 7-MEOTA
Jan Korabecny, Ondrej Holas, Kamil Musilek,
Miroslav Pohanka, Veronika Opletalova, Vlastimil Dohnal and
Kamil Kuca
Formerly, 9-amino-7-methoxy-1,2,3,4-tetrahydroacridine (7-MEOTA)
was investigated as promising tacrine analogue beneficial
for its low toxicity compared to tacrine. In this study, novel
7-MEOTA derivatives were synthesized – namely - 9,9`-di-(alkane-1,ω-diyldiimino)-di-(7-methoxy-1,2,3,4-tetrahydroacridine)
was prepared from the corresponding diiodoalkanes. The novel
compounds exhibit anticholinesterase (acetylcholinesterase
and butyrylcholinesterase) activity in vitro. The
synthesis and in vitro data are summarized in this
article.
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Article]
Novel Synthesis of 3-Arylated 5,6-Dimethoxybenzo[d]isothiazole
1,1-Dioxides
Fei Xie, Bing-Lei Gao, De-Feng Wang and
Zhao-Peng Liu
A novel simple three-step synthesis of 3-arylated 5,6-dimethoxybenzo[d]isothiazole
1,1-dioxide is reported. ortho-Lithiation of N-tert-butyl-3,4-dimethoxybenzenesulfonamide
followed by reaction with aryl aldehydes gave carbinol sulfonamides,
which were oxidized into ketosulfonamides and converted to
the ketimines via TMSCl/NaI/MeCN reagent mediated
novel cyclization.
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Synthesis of the α-Tocopheramine-15N
Model Compound 2,2,5,7,8- Pentamethyl-6-chromanylamine-15N
Stefan Böhmdorfer, Lars Gille and
Thomas Rosenau
2,2,5,7,8-Pentamethyl-6-chromanylamine-15N
was prepared by condensation of ZnCl2-catalyzed
condensation of 2,3,5-trimethylphenol with isoprene, followed
by conversion of the resulting chroman into the 6-nitro-derivative
and further reduction to the title compound, which possesses
a 2-methyl group instead of the isoprenoid side chain of tocopherols
and tocopheramines. Tocopheramines and their short-chain analogues
are current targets in medicinal chemistry and anti-cancer
research.
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Antiradical Activity of β-Ionyl
Compounds
Anil K. Singh and Solomon B. Libsu
Antioxidant potential of some β-ionyl
compounds has been assessed by examining their ability to
protect methyl linoleate from aerial and 2,2’-azobisisobutyronitrile-induced
radical-mediated oxidation. It is observed that the π-electron
density of β-ionyl
structure is an important factor in the antiradical activity
of these compounds.
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Chiral Ionic Liquid Mediated Diels-Alder Reaction
Between Anthrone Enolate and Maleimides
Nitin A. Mirgane, Mohammed H.H. Akhtar and
Anil V. Karnik
A chiral ionic liquid, 1-butyl-3-methylimidazolium (T-4)-bis[(2S)-2-(hydroxy-κO)
propanoato-κO]borate
(BMIm+BLLB-),
has been used as organocatalyst and asymmetric inducer in
Diels-Alder reactions between anthrone and various maleimides.
This greener solvent makes the reaction faster, proceeds with
quantitative yields and exhibits moderate enantioselectivity.
Stereochemical outcome suggests a more organized transition
state in ionic liquid involving hydrogen bonding and polar
interactions.
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