Organic Communications

A scientific open acces journal in the field of synthetic organic chemistry and polymers
Editor-in-Chief: Hasan Seçen
Book Review and Review Article Editor: Turan Ozturk
Synthetic Polymer Section Editor: Mehmet S. Eroglu

LATEST ARTICLES

Communication

Org. Commun. (2018) 11:3 ; 168 - 172
by Jacob T. Heppell, Wah Chin Boon and Jasim M. A. Al-Rawi
Abstract

 The synthesis of (E)-10-hydroxy-2-decenoic acid ethyl ester (10H2DA-EE) (3) was achieved via a one-pot, tandem oxidation-Wittig process from commercially available 1,8-octanediol (1), Wittig reagent (Ph3P=CHCO2Et) (2) and activated MnO2. Subsequent hydrolysis with sodium hydroxide gave (E)-10-hydroxy-2-decenoic acid (10H2DA) (4).

Keywords
One-pot tandem oxidation-Wittig process (E)-10-hydroxy-2-decenoic acid ethyl ester (E)-10-hydroxy-2decenoic
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© 2018 ACG Publications. All rights reserved.
Original Article

Org. Commun. (2018) 11:3 ; 163 - 167
by Aliye Altundas and Berna Gül Aslan
Abstract

One pot syntheses of six-, seven-membered cycloalkane and pyrane junctured aminocyanopyridines bearing furan unit were successfully prepared from the ketones, 2-((5-methylfuran-2-yl)methylene) malononitrile, and ammonium acetate. Photooxygenation of 2-(4-aminocyanopyridine) substituted 5-methylfurans gave 1,4-dicarbonyl functionalized aminocyanopyridine derivatives in good yield in one single operation.

Keywords
4-Furyl-2-amino-3-cyanopyridines singlet oxygene 4-oxopent-2-enoylnicotinonitrile.
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© 2018 ACG Publications. All rights reserved.
Original Article

Org. Commun. (2018) 11:3 ; 149 - 162
by Mohd Fazli Mohammat, Muhammad Siddiq Maarop, Zurina Shaameri, Agustono Wibowo, Saiful Azmi Johari and Ahmad Sazali Hamzah
Abstract

A practical and efficient synthesis of non-spiro and spiropyrano[2,3-c]pyrazole-3-carboxylate derivatives was developed. The synthesis was achieved via a domino one-pot, four-component reaction of diethyl oxaloacetate, hydrazine, aldehyde and malanonitrile in refluxing acidic ethanolic solution under non-catalytic system. This method is rapid, simple and provides products in good yields and can be accessed via different classes of carbonyls, malanonitriles and hydrazine derivatives. Mechanistic study envisaged that this domino four-component reaction proceeds via sequential reactions of pyrazolone formation, Michael reaction and Thorpe-Ziegler cyclization reaction. Strong electronic effects of Knoevenagel and pyrozolone product contribute significantly towards successful cyclization of the title compounds.

Keywords
Pyrano[2 3-c]pyrazole-3-carboxylate diethyloxaloacetate Michael reaction
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© 2018 ACG Publications. All rights reserved.
Original Article

Org. Commun. (2018) 11:3 ; 142 - 148
by İnci Selin Doğan, Hasan Erdinç Sellitepe, Nuran Kayıkçı, Hande Sipahi, Rengin Reis and Nurettin Yaylı
Abstract

A series of five –CH3, -NO2, -OCH3 and -Cl substituted 2-hydroxy-2,2-bis(4-phenyl)-N'-[(1E)-(3/4-phenyl)methylene]acetohydrazide (1a-1e) was synthesized by the reaction of 2-hydroxy-2,2-diphenylacetohydrazide with substituted aromatic aldehydes to give intermediate Schiff bases. Structures of the synthesized compounds were characterized using NMR (1D; 1H, 13C/APT and 2D 1H-1H COSY, and NOESY), FT-IR, UV, LC-MS/MS spectral data and elemental analysis. The geometry of compounds 1a-1e were determined to be “E” by NOESY. All the tested compounds showed cytotoxic activity on MCF-7 and PC-3 cell line at highest experimental concentration (100 µM). Compounds 1b (18.24 ± 7.62 µM) and 1e (7.62 ± 1.85 µM) have strong anti-proliferative activity on MCF-7 cell line, while compound 1b (45.81 ± 1.10 µM) has the strongest activity on PC-3 cell line.

Keywords
2-Hydroxy-2 2-diphenylacetic acid acetohydrazide derivatives MCF-7 PC-3.
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© 2018 ACG Publications. All rights reserved.