Organic Communications

Year: 2017 Volume: 10 Issue:1 January-March

Original Article

1) An unexpected aromatization reaction during the preparation of 1,2-cyclohexanedione ethers

Org. Commun. (2017) 10:1 ; 1 - 5
by Ryan DeAngelis, Amy Solinski and David A. Hunt

In a heretofore-unreported reaction, 1,2-cyclohexandione reacts with a variety of alcohols under mild acid-catalyzed dehydration conditions to afford not only ethers of 1,2- cyclohexanedione but the corresponding aryl ethers as well in moderate to good yield.

DOI
http://doi.org/10.25135/acg.oc.1.16.07.425
Keywords
1 2-cyclohexanedione aromatization aryl ethers
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Original Article

2) Synthesis of 13C labeled β-cyano-ʟ-alanine

Org. Commun. (2017) 10:1 ; 6 - 10
by Nesa Ghasemi and Hasan Seçen

A synthetic methodology for preparation of β-cyano-ʟ-alanine was developed via ʟ -serine. Esterification of ʟ -serine with MeOH, followed by protection of NH 2 with CBz, gave methyl 2-(benzyloxycarbonylamino)-3-hydroxypropanoate. Mesylation of OH group, and then cyanation, ester hydrolysis and removal of the CBz group with catalytic hydrogenation, gave β-cyano-ʟ-alanine. Crucial step for the synthesis of the title compound was cyanation with K 13CN.

DOI
http://doi.org/10.25135/acg.oc.2.16.08.502
Keywords
β-cyano-ʟ-alanin e labeled amino acid asparagine
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Original Article

3) The interaction between (o-acetylphenyl)ferrocene and metal ions

Org. Commun. (2017) 10:1 ; 11 - 14
by Shoko Yamamoto and Yutaka Okada

The oxidation reaction of ferrocene derivatives is important because of its biological applications. The reactivity is affected by metal ions. However, it is not clear how to interact the metal ions with the ferrocenes. In this paper, the oxidation reactivity of (o-acetylphenyl)ferrocene was investigated in the view of solvent effect and the addition effect of salicylic acid. Furthermore, the measurement of the relaxation time was carried out. As a result, Al 3+ would strongly interact with (o-acetylphenyl)ferrocene so that prevent the mobility of the acetyl group.

DOI
http://doi.org/10.25135/acg.oc.3.16.09.434
Keywords
Ferrocene derivatives metal ion oxidation reaction solvent effect relaxation time salicylic acid
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Original Article

4) Synthesis of some natural sulphonamide derivatives as carbonic anhydrase inhibitors

Org. Commun. (2017) 10:1 ; 15 - 23
by Taner Gokcen, Melike Al , Meryem Topal, Ilhami Gulcin, Turan Ozturk and Ahmet C. Goren

Carbonic anhydrase inhibitors are both in clinical use as antiglaucoma, diuretics, antiepileptics and management of altitude sickness, and under investigation as anticancer, anticonvulsant and antiobesity agents. Sulphonamides have been known for decades as carbonic anhydrase inhibitors and are in clinical use. Sulphonamide derivatives of p-hydroxybenzoic acid and 3,4,5-trihydroxybenzoic acid (gallic acid) were synthesized and their inhibition values over hCA I and hCA II isozymes, purified from human erythrocyte cells by Sepharose-4B-L-tyrosine-sulphanilamide, were determined. Compounds synthesized showed efficient carbonic anhydrase inhibition activity at low nM levels.

DOI
http://doi.org/10.25135/acg.oc.4.16.05.418
Keywords
Carbonic anhydrase inhibitor sulphonamides p-hydroxybenzoic acid 3 4 5-trihydroxybenzoic acid (gallic acid)
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Original Article

5) Convenient synthesis and characterization of some novel benzothiazolone-based Schiff bases as potential pharmaceutically active agents

Org. Commun. (2017) 10:1 ; 24 - 31
by Hanane Chabane, Yasmina Adjeroud and Messaoud Liacha

A novel series of Schiff bases derivatives containing the benzothiazolone moiety have been synthesized in a simple and efficient method, by condensation of 6- amino-2(3H)-benzothiazolone substrates with different aromatic aldehydes, in refluxing ethanol and in the presence of acetic acid as catalyst. The structure of synthesized compounds was elucidated and has been proven using spectral methods such as 1 H NMR, 13C NMR and elemental analysis . All the newly synthesized compounds were in good agreement with the proposed structures.

DOI
http://doi.org/10.25135/acg.oc.5.16.05.420
Keywords
Schiff bases 2(3H)-benzothiazolone 6- amino - 2(3H)-benzothiazolones aromatic aldehydes
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Original Article

6) Synthesis and antibacterial activity of 2-amino chromenes arising cyanoiminocoumarins and β-naphthol

Org. Commun. (2017) 10:1 ; 32 - 39
by Lamia Dammak, Mariem Kammoun, Noureddine Allouche, Houcine Ammar and Souhir Abid

The synthesis of 2-amino chromene, reported in our previous paper, has been accomplished by the reaction of cyanoiminocoumarin and β-naphthol . The obtained compound was reacted   with various electrophilic or nucleophilic reagents. All the new homologous 2-amino-4H-chromenes have been characterized on the basis of their spectral (IR, 1H and 13C NMR) data and microanalysis. Four compounds were evaluated   in vitro  for their preliminary antibacterial activities against five different pathogenic bacterial strains such as Bacillus thuringiensis , Escherichia coli , Staphylococcus aureus, klebsiella pneumonia and Salmonella Sp . Antibacterial activity of each compound was compared with standard drug, Penicillin.

DOI
http://doi.org/10.25135/acg.oc.6.16.11.442
Keywords
Cyanoiminocoumarins 2-amino-4H-chromene β-naphtol antibacterial activity
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Original Article

7) A pre-biotinylated linker assembly for single-step preparation of novel biosensors

Org. Commun. (2017) 10:1 ; 40 - 45
by Brent A. Banasik

A simple and efficient method for the synthesis of biotin pre-functionalized linkers via orthogonal protecting group elongation strategy is reported for a single-step preparation of new biosensor probes. The target compound 4- (4- (4- (5- ((3S, 4S, 6R)-2-oxohexahydro-1H-thieno[3,4]imidazol-4-yl) pentanamido) butanamido) butanamido) butanoic acid (5) was synthesized in five linear steps with a 40% overall yield.

DOI
http://doi.org/10.25135/acg.oc.7.16.12.451
Keywords
biosensor linker biotin lagunamide
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Original Article

8) Cellulose-SO3H catalyzed synthesis of bis(α-aminophosphonates) and their antioxidant activity

Org. Commun. (2017) 10:1 ; 46 - 55
by Nemallapudi Bakthavatchala Reddy, Chereddy Syama Sundar, Balam Satheesh Krishna, Sarva Santhisudha, Poola Sreelakshmi, Sandip Kumar Nayak and Cirandur Suresh Reddy

A simple and efficient synthesis of bis(α-aminophosphonates) has been developed by the reaction of aromatic aldehydes, 1,4-phenylenediamine and diethylphosphite in the presence of cellulose-SO 3H as catalyst under neat conditions at room temperature for 10-30 minutes. The synthesized compounds were screened for their antioxidant activity against DPPH, NO and H 2O 2 scavenging methods. All the compounds exhibited good to moderate activity.

DOI
http://doi.org/10.25135/acg.oc.8.16.06.422
Keywords
Bis(α-aminophosphonates) 1 4-phenylenediamine diethylphosphite cellulose-SO 3H antioxidant activity
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