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

Short Communication

The halogen effect on the ring-opening of germacyclopropylidenoids to germaallenes

Org. Commun. (2019) 12:2 ; 115 - 119
by Cem B. Yildiz and Akın Azizoğlu

Density functional theory calculations were employed to explore the ring–opening reaction mechanisms of mono germanium analogues of cyclopropylidenoids via Doering–Moore–Skattebøl method. The theoretical findings revealed that the stepwise fashion with the intermediacy of a free germacyclopropylidene is operative for the structure with germanium atom on the carbenic position (1). Moreover, the cyclopropylidene analogue (4) of the title structures proceeds via concerted manner for the corresponding ring-opening reaction. The calculated overall energy barrier to trigger the stepwise ring-opening reaction for 1 is strongly higher than the concerted fashion for 4. Additionally, the effect of halogens (X = F, Cl, Br) on the reaction mechanism were also investigated. The energy barriers for chlorine substituted precursors are found to be lower than the fluorine and bromine substituted forms.

DOI
http://doi.org/10.25135/acg.oc.59.19.05.1297
Keywords
Germaallene reaction mechanism DFT germanoid germylene
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© 2019 ACG Publications. All rights reserved.
Original Article

An efficient and eco-friendly synthesis of 1, 4-dihydropyridines via Hantzsch reaction in Glycine-HCl buffer as solvent and bio-catalyst

Org. Commun. (2019) 12:2 ; 109 - 114
by Ali Reza Molla Ebrahimlo , Mounes Hanaforoush and Roya Attari

A green and efficient procedure was established to synthesize 1,4-dihydropyridines via one-pot Hantzsch reactions in buffering conditions without the use of organic solvent. In this method, a buffer solution was used as solvent and catalyst reaction; therefore, using this method has several benefits including high yields, an environmentally friendly procedure, short reaction times, and a simple work-up procedure. All the compounds were characterized by TLC, FT-IR, 1H NMR and elemental studies. 

 

DOI
http://doi.org/10.25135/acg.oc.58.19.05.1273
Keywords
Hantzsch reaction 1,4-dihydropyridines glycine-HCl buffer green procedure
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© 2019 ACG Publications. All rights reserved.
Original Article

Oxidation of hesperidin into diosmin using ionic liquids

Org. Commun. (2019) 12:2 ; 101 - 108
by V-thanh Nguyen , T.kim-chi Huynh , Thanh-danh Nguyen and Kim-dung Hoang

In this study, ionic liquids (ILs) were first used as solvents for conversion of hesperidin into diosmin. The diosmin was successfully synthesized by using iodine oxidation in ionic liquids including [BMIM]Br, [BMIM]BF4, [BMIM]OTf, [BPY]Br, [BPY]BF4 and [BPY]OTf.  The results showed the reaction achieved in good yields (57- 76%). Among them, [BPY]Br and [BPY]BF4 exhibited as excellent solvents for the oxidation of hesperidin. In particular, water content in recovered ionic liquids (ILs), which affected strongly recyclable performance in the oxidation of hesperidin, has been investigated. It found that water content in [BPY]Br  from 1 % to 5% (v/v) induced a significant increase of the synthetic yield.

DOI
http://doi.org/10.25135/acg.oc.57.19.04.1242
Keywords
diosmin oxidation hesperidin synthesis ionic liquid
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© 2019 ACG Publications. All rights reserved.
Review Article

3-Acyl(aroyl)coumarins as synthon in heterocyclic synthesis

Org. Commun. (2019) 12:2 ; 43 - 100
by Wafaa S. Hamama , Moged A. Berghot , Eman El Baz , Essam H. A. Hanashalshahaby and Moustafa Ahmed Gouda

This review presents a systematic and comprehensive survey of the chemical reactivity of 3-acyl(aroyl) coumarins. The target compounds are important intermediates for the synthesis of a variety of synthetically useful and novel heterocyclic systems with different ring sizes such as isoxazole, pyrazole, 3H-triazolium salts, pyrimidine, pyridine, quinolone, benzoxocin, benzoxonin and benzoxepin.

 

 

DOI
http://doi.org/10.25135/acg.oc.5619.02.1160
Keywords
Coumarins Pyrazoles Thiazole Pyridine Heterocyclic Reduction
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© 2019 ACG Publications. All rights reserved.