Letters in Organic Chemistry, Volume 2, No. 4, 2005
Contents
Advances in 1,3-Dipolar Cycloaddition Reaction of Azides and Alkynes – A Prototype of “Click” Chemistry Pp.293-301
Qian
Wang, Srinivas Chittaboina and Hannah N. Barnhill
Letters in Organic Chemistry
Effect of Additional Chiral Ligands in Catalytic
Enantioselective Addition of Ketene Silyl Acetals to Nitrones Pp.302-305
P.
Merino, S. Franco, P. Jimenez, T. Tejero and M.A. Chiacchio
A Novel Route Towards the Synthesis of Stereospecific N-Substituted
Chiral Morpholines Pp.306-308
Raid
J. Abdel-Jalil, Syed Tasadaque Ali Shah, Khalid Mohammed Khan and Wolfgang
Voelter
A Convenient, Highly Selective Iodination Method for
Alcohols Using Cesium Iodide/Aluminum Chloride Pp.309-311
Khalid
Mohammed Khan, Zia-Ullah, Shahnaz Perveen, M. Iqbal Choudhary, Atta-ur-Rahman
and Wolfgang Voelter
A Stereoselective Aldol–Reduction Approach to
Polyoxygenated Natural Products. Synthesis of C1–C6 Fragment of Erythronolides Pp.312-315
Marta
Galobardes, Miguel Gascon, Pedro Romea and Felix Urpi
Stereoselective Preparation of 1-Deoxy-Homonojirimycin
from a b- Ketoester Bearing
Sugar Pp.316-318
C.
Thomassigny, M.T. Barroso and C. Greck
Highly Stereoselective Alkynylation with Steroidal
Alkyne: Efficient Pathway to 24(S) or 24(R)-Hydroxylcholesterol Pp.319-322
Biao
Jiang, Zi-li Chen and Hao Huang
Design of Photo-Reactive Fluorescent Glycosyl Donor for
Fabrication of Carbohydrate-Based Functional Materials Pp.323-329
Masaya
Suzuki, Yuya Ohguro, Yoshihiro Nishida, Masaki Miyamoto and Kazukiyo Kobayashi
A Simple and Effective Method for the Thionation of
Amides to Thioamides Using Al2O3-Supported P4S10
Pp.330-333
Jacques
H. Poupaert, Pascal Carato and Christopher R. McCurdy
Microwave and Classical Activation of Solvent-Free
Reactions of Nisopropyl Arylidene Amines with Alkyl Cyanoacetates Pp.334-339
Ludovic
Paquin, Loic Toupet, Jack Hamelin and Francoise Texier-Boullet
Synthesis of Quinolindione Derivatives Assisted by
Microwave Irradiation Pp.340-342
Pietro
Campiglia, Teresa Lama, Francesco Aiello, Isabel M. Gomez-Monterrey, Maria V.
Diurno, Ettore Novellino and Paolo Grieco
Synthesis of 9-[2-O-(2-Methoxyethyl)-b-D-Ribofuranosyl]purines Using
1-Methanesulfonyloxy-2-Methoxyethane Pp.343-348
Grigorii
G. Sivets, Jouko Vepsalainen and Igor A. Mikhailopulo
DNA-Binding Fourfold Spermine Functionalized Perylene
Bisimide Dye Pp.349-353
Stefanie
Krauß, Marina Lysetska and Frank Wurthner
Natural Phosphate Modified with Sodium Nitrate: New
Efficient Catalyst for the Construction of a Carbon-Sulfur and Carbon-Nitrogen
Bonds Pp.354-359
Mohamed
Zahouily, Hind Charki, Younes Abrouki, Bahija Mounir, Bouchaib Bahlaouan, Ahmed
Rayadh and Said Sebti
FeCl3 and FeCl3-SiO2
Catalysed Selective p-Methoxybenzylation of Alcohols with p-Methoxybenzyl
Alcohol (PMB-OH) Pp.360-363
Palakodety
Radha Krishna, B. Lavanya, A.K. Mahalingam, V.V. Ramana Reddy and G.V.M. Sharma
Formation of Highly Functionalized
Hydrindanes and Hydroazulenes via Polyene Cyclization Promoted by the Cross
Conjugated a-Carbomethoxy Enone System Pp.364-366
Hsing-Jang Liu, Daqing Sun, Floria
Roa-Gutierrez and Kak-Shan Shia
Original Intramolecular SRN1 Reaction in
Naphthoquinone Series Pp.367-370
Thierry
Terme, Abdelouahab Beziane and Patrice Vanelle
Chloromethoxymethyl Polystyrene (CMM Resin), an Acid
Labile Resin for Anchoring/Cleavage of N-Heterocycles and Oxygen Aromatic
Compounds Pp.371-373
Marta
Marfil, Fernando Albericio and Mercedes Alvarez
A Very Efficient Synthesis of (1H)-1,5-Diazaanthracene-2,9,10-triones
Pp.374-377
J.
Ignacio Ubeda, Mercedes Villacampa and Carmen Avendano
Synthesis of 6-Amino-1H-Indole-4,7- Quinones Pp.378-381
Eveline
Pringel, Jacques Gentili, Raphael Terreux, Bernard Fenet and Roland Barret
Abstracts
[Back to top] Advances in 1,3-Dipolar Cycloaddition Reaction of
Azides and Alkynes – A Prototype of “Click” Chemistry
Qian
Wang, Srinivas Chittaboina and Hannah N. Barnhill
Click chemistry, designated by Sharpless and his coworkers, is a modular approach that uses only the most practical and reliable chemical transformations. The Huisgen reaction, especially the newly developed copper(I)-catalyzed 1,2,3-triazole formation reaction between azides and alkynes, is regarded as the “cream of the crop” of click chemistry. In this review, we introduce the recent development of this reaction, and highlight some of its important applications in drug discovery, bioconjugation chemistry, materials development and surface modification.
[Back to top] Effect of Additional Chiral Ligands in Catalytic
Enantioselective Addition of Ketene Silyl Acetals to Nitrones
P.
Merino, S. Franco, P. Jimenez, T. Tejero and M.A. Chiacchio
The enantioselectivity of the titanium (IV)-BINOL catalyzed asymmetric Mannich-type reactions of nitrones can be enhanced by using additional chiral ligands. The best results are obtained with diols derived from D-mannitol.
[Back to top] A Novel Route Towards the Synthesis of Stereospecific N-Substituted
Chiral Morpholines
Raid
J. Abdel-Jalil, Syed Tasadaque Ali Shah, Khalid Mohammed Khan and Wolfgang
Voelter
In this communication a convenient and novel method for the synthesis of chiral N-substituted-(arabinopyrano)[3,4-b]morpholines of pharmacological interest from anhydro sugars is described.
[Back to top] A Convenient, Highly Selective Iodination Method for
Alcohols Using Cesium Iodide/Aluminum Chloride
Khalid
Mohammed Khan, Zia-Ullah, Shahnaz Perveen, M. Iqbal Choudhary, Atta-ur-Rahman
and Wolfgang Voelter
A variety of allyl and benzyl alcohols are converted into their corresponding iodides using cesium iodide (CsI) in the presence of aluminum chloride (AlCl3) in acetonitrile under mild conditions.
[Back to top] A Stereoselective Aldol–Reduction Approach to
Polyoxygenated Natural Products. Synthesis of C1–C6 Fragment of Erythronolides
Marta
Galobardes, Miguel Gascon, Pedro Romea and Felix Urpi
A new synthetic approach directed toward the preparation of C1–C6 fragment of erythronolides is disclosed. The core of the process takes advantage of a highly stereoselective sequence based on a boron– mediated aldol reaction of a lactate–derived chiral ketone followed by a syn-reduction of the resulting adduct.
[Back to top] Stereoselective Preparation of 1-Deoxy-Homonojirimycin
from a b- Ketoester Bearing
Sugar
C.
Thomassigny, M.T. Barroso and C. Greck
We present in this note the preparation of 1,5,6-trideoxy-1,5-imino-D-gluco-heptitol commonly known as 1-deoxy-homonojirimycin by a diastereoselective way. The polyhydroxylated piperidine has been obtained from a β-ketoester bearing a xylofuranose moiety.
[Back to top] Highly Stereoselective Alkynylation with Steroidal Alkyne:
Efficient Pathway to 24(S) or 24(R)-Hydroxylcholesterol
Biao
Jiang, Zi-li Chen and Hao Huang
24(S)- or 24(R)-Hydroxyl cholesterol was prepared in high stereoselectivity (up to 99% de), utilizing asymmetric alkynylation of isobutyraldehyde with steroidal alkyne catalyzed by Zn(OTf)2 respectively in the presence of (1S, 2S)-3-(t-butyldimethylsilyloxyl)-2-N, N-dimethylamino-1-(p-nitrophenyl)- propane-1-ol or its (1R, 2R)-enantiomer.
[Back to top] Design of Photo-Reactive Fluorescent Glycosyl Donor for
Fabrication of Carbohydrate-Based Functional Materials
Masaya
Suzuki, Yuya Ohguro, Yoshihiro Nishida, Masaki Miyamoto and Kazukiyo Kobayashi
As a reagent for fabrication of carbohydrate-based functional materials, we prepared a photo-reactive fluorescent glycosyl reagent carrying α-mannoside and 4-azidophenyl group in our previous fluorescent β- peptide skeleton. The reagent increased fluorescence upon UV-irradiation in methanol, demonstrating its high potential utility.
[Back to top] A Simple and Effective Method for the Thionation of Amides
to Thioamides Using Al2O3-Supported P4S10
Jacques
H. Poupaert, Pascal Carato and Christopher R. McCurdy
A simple and effective method for the thionation of amides to thioamides using Al2O3-supported P4S10 was developed and applied to a series of amides including some heterocyclic examples. The reaction was best performed in anhydrous dioxane at reflux temperature. Yields ranging from 62 – 93% are comparable to, or superior to those obtained with Lawesson’s reagent. The method uses inexpensive reagents and has the advantage that reagent-derived byproducts may be removed by a simple hydrolytic workup rather than by chromatography, as required for Lawesson’s reagent.
[Back to top] Microwave and Classical Activation of Solvent-Free
Reactions of Nisopropyl Arylidene Amines with Alkyl Cyanoacetates
Ludovic
Paquin, Loic Toupet, Jack Hamelin and Francoise Texier-Boullet
Neat imine 1a with alkylcyanoacetate 2 leads to new cyclohexenes by Michael-Michael initiated ring closure reaction at RT or under classical heating. Surprisingly, this cyclohexene is not formed under microwave. This is the first example of a reaction working under classical activation and not under microwaves. A mechanism and an explanation are proposed.
[Back to top] Synthesis of Quinolindione Derivatives Assisted by
Microwave Irradiation
Pietro
Campiglia, Teresa Lama, Francesco Aiello, Isabel M. Gomez-Monterrey, Maria V.
Diurno, Ettore Novellino and Paolo Grieco
The synthesis of new dihydrothieno[2,3-g and 3,2-g](iso)quinoline-4,9-dione derivatives, as potential templates in development of new cytotoxic agents, was realized using microwave irradiation methodology.
[Back to top] Synthesis of 9-[2-O-(2-Methoxyethyl)-b-D-Ribofuranosyl]purines Using
1-Methanesulfonyloxy-2-Methoxyethane
Grigorii
G. Sivets, Jouko Vepsalainen and Igor A. Mikhailopulo
1-Methanesulfonyloxy-2-methoxyethane (1; MsO-MOE) was used for alkylation of adenosine and 2-aminoadenosine. 2’-O-MOE derivatives of adenosine (3), 2-aminoadenosine (7) and guanosine (10) have been prepared in 47, 44 and 81% isolated yields, respectively. The stereochemistry of the pentofuranose rings of the isomeric 2’-O-MOE and 3’-O-MOE purine nucleosides is very similar and, moreover, alkylation of either 2’- or 3’-hydroxyls has practically no effect upon the stereochemistry of the parent nucleosides.
[Back to top] DNA-Binding Fourfold Spermine Functionalized Perylene
Bisimide Dye
Stefanie
Krauß, Marina Lysetska and Frank Wurthner
A spermine functionalized perylene bisimide dye has been synthesized which is highly water soluble at neutral pH and binds effectively to DNA through electrostatic interactions as confirmed by fluorescence and AFM studies.
[Back to top] Natural Phosphate Modified with Sodium Nitrate: New
Efficient Catalyst for the Construction of a Carbon-Sulfur and Carbon-Nitrogen
Bonds
Mohamed
Zahouily, Hind Charki, Younes Abrouki, Bahija Mounir, Bouchaib Bahlaouan, Ahmed
Rayadh and Said Sebti
The modification on natural phosphate (NP) with sodium nitrate by calcination catalyzed Michael addition of mercaptans and amines to chalcone derivatives with high yields under mild reaction conditions. By-products of usual undesirable reaction in Michael condensation such as 1,2-addition, bis-addition and polymerization are not observed. The work-up procedure is simplified by simple filtration with the use of Na/NP-2. This catalyst is used for the facile synthesis of b-amino acid and b-amino diacid under heterogeneous conditions.
[Back to top] FeCl3 and FeCl3-SiO2
Catalysed Selective p-Methoxybenzylation of Alcohols with p-Methoxybenzyl
Alcohol (PMB-OH)
Palakodety
Radha Krishna, B. Lavanya, A.K. Mahalingam, V.V. Ramana Reddy and G.V.M. Sharma
Anhydrous FeCl3 and FeCl3-SiO2 serve as Lewis acids for direct conversion of alcohols into p-methoxybezyl ethers using PMB-OH in good yields, the latter reagent was found to be effective in not only converting primary, allylic and propargylic alcohols selectively but also the pre-existing acid sensitive groups remained unscathed.
[Back to top] Formation of Highly Functionalized Hydrindanes and
Hydroazulenes via Polyene Cyclization Promoted by the Cross Conjugated a-Carbomethoxy Enone System
Hsing-Jang
Liu, Daqing Sun, Floria Roa-Gutierrez and Kak-Shan Shia
The polyene cyclization promoted by the cross conjugated a-carbomethoxy enone system has been successfully applied to facilitate the construction of the hydridane and hydroazulene framework containing a high level of functionalization.
[Back to top] Original Intramolecular SRN1 Reaction in
Naphthoquinone Series
Thierry
Terme, Abdelouahab Beziane and Patrice Vanelle
We report here the synthesis of a new cyclopenta[b]naphthalene-4,7-dione via the first example of intramolecular electron transfer reaction from naphthoquinonic alkylating agent bearing a nitroalkane group at the position 3.
[Back to top] Chloromethoxymethyl
Polystyrene (CMM Resin), an Acid Labile Resin for Anchoring/Cleavage of N-Heterocycles
and Oxygen Aromatic Compounds
Marta
Marfil, Fernando Albericio and Mercedes Alvarez
A novel linker for the solid-phase anchoring of heterocycles and phenol compounds is described.
[Back to top] A Very
Efficient Synthesis of (1H)-1,5-Diazaanthracene-2,9,10-triones
J.
Ignacio Ubeda, Mercedes Villacampa and Carmen Avendano
Acylation of ortho-lithiated species derived from N,O-dipivaloyl-6-amino-5,8-dimethoxy-4-methyl- 2(1H)-quinolinone, followed by condensation with carbonyl reagents and in situ N-deprotection gave 7-alkyl or 6,7-dialkyl-9,10-dimethoxy-4-methyl-1,5-diaza-2(1H)-anthracenones, which were finally oxidised to the title compounds.
[Back to top] Synthesis
of 6-Amino-1H-Indole-4,7- Quinones
Eveline
Pringel, Jacques Gentili, Raphael Terreux, Bernard Fenet and Roland Barret
The addition of amines to N-benzenesulfonylindoloquinone and the regiochemistry of the products are studied.