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

Synthesis of (E)-10-hydroxy-2-decenoic acid ethyl ester via a one-pot tandem oxidation-Wittig process

Org. Commun. (2018) in press ; 1 - 5
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).

DOI
http://doi.org/10.25135/acg.oc.48.18.06.106
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
One-pot tandem oxidation-Wittig process (E)-10-hydroxy-2-decenoic acid ethyl ester (E)-10-hydroxy-2decenoic
Available online: September 12, 2018
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Original Article

Synthesis and anticancer (MCF-7, PC-3) activities of new 2-hydroxy-2,2-bis(4-substitutedphenyl)-N'-[(1E)-(3/4- substitutedphenyl)methylene]-acetohydrazides

Org. Commun. (2018) in press ; 1 - 7
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.

DOI
http://doi.org/10.25135/acg.oc.47.18.06.107
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
2-Hydroxy-2 2-diphenylacetic acid acetohydrazide derivatives MCF-7 PC-3.
Available online: September 04, 2018
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Original Article

Practical synthesis and electronic study of non-spiro and spiropyrano[2,3-c]pyrazole-3-carboxylate derivatives via uncatalyzed domino one-pot, four-component reactions

Org. Commun. (2018) in press ; 1 - 14
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.

DOI
http://doi.org/10.25135/acg.oc.46.18.05.104
(DOI number will be activated after the manuscript has been available in an issue.)
Keywords
Pyrano[2 3-c]pyrazole-3-carboxylate diethyloxaloacetate Michael reaction
Available online: September 04, 2018
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© ACG Publications. All rights reserved.