Open Access Published by De Gruyter

Volume 20 Issue 3

Issue of Heterocyclic Communications

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Contents
Journal Overview

Publicly Available May 28, 2014

Frontmatter

Page range: i-iii

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Review

Open Access May 28, 2014

Synthesis and reactivity of heterocyclic hydroxylamine-O-sulfonates

Jarosław Sączewski, Martyna Korcz

Page range: 133-147

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Abstract

The heterocyclic hydroxylamine- O -sulfonates constitute a novel family of formal O -substituted hydroxyguanidines and hydroxyamidines that serve as functional precursors to a variety of fused heterocyclic ring systems incorporating N-N, N-O, N-S, or N-N + moiety. They are readily accessible from the reaction of 2-chloroazoles, 2-chloroazines, and 2-chlorodiazines with hydroxylamine- O -sulfonic acid. They have a rich chemistry exemplified by tandem reactions, such as nucleophilic addition-electrophilic amination, nucleophilic addition-electrophilic 5- endo-trig cyclization or fluorogenic Mannich-electrophilic amination reaction. The heterocyclic hydroxylamine- O -sulfonates have significant potential for use in synthesis of anticancer, antiviral, and antimicrobial agents. The newly discovered fluorogenic reaction and fluorescent dyes (Safirinium-P and Safirinium-Q) have found applications in fluorescent detection and labeling.

Preliminary Communication

Open Access May 28, 2014

Synthesis of pyridine derivatives as potential antagonists of chemokine receptor type 4

Suazette Reid Mooring, Theresa Gaines, Zhongxing Liang, Hyunsuk Shim

Page range: 149-153

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Abstract

A series of pyridine derivatives were synthesized as potential inhibitors of chemokine receptor type 4. This chemokine receptor has been linked to various disease pathways including HIV-1 proliferation, autoimmune disorders, inflammatory diseases, and cancer metastasis. The compounds were tested for activity using an affinity binding assay and an assay that tests the ability to inhibit cell invasion. Two hit compounds ( 2b and 2j ) have been identified for further evaluation that inhibit cell invasion by at least 50% and have an effective concentration of less than 100 n m in the binding affinity assay. The structures of the synthesized compounds were confirmed by spectral data.

Research Articles

Open Access May 28, 2014

Design and synthesis of novel active phosphonate esters and their application in preparation of ceftriaxone

Hui-xue Ren, You-min Sun, Dao-ji Wu, Yong-shan Ma, Han-jie Ying, Yan Ma

Page range: 155-159

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Abstract

For a series of active phosphonate esters, the anhydride abbreviated as ANPTA ( 6a ) exhibits the highest reactivity in the preparation of ceftriaxone. The synthesis of ceftriaxone was optimized with the pilot-scale yield reaching 95.7%. The results were explained from the structural viewpoint and supported by analysis of the calculated Mulliken atomic charge distribution.

Open Access May 28, 2014

Synthesis of novel oxepine-containing polycyclic-fused quinoline systems

Wentao Gao, Chengming Nie, Liangyu Xu, Binbin Zhao, Yang Li

Page range: 161-166

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Abstract

In the present investigation, the incorporation of the oxepine ring into a polycyclic-fused quinoline system leading to a series of structurally novel hybrids benzo[ h ]areno[6,7]oxepino[3,4- b ]quinolin-8(14 H )-ones has been achieved through a simple, and economical two-step procedure that involves the one-pot synthesis of 2-(aryloxymethyl)benzo[ h ]quinoline-3-carboxylic acids followed by intramolecular Friedel-Crafts acylation reaction using Eaton’s reagent.

Open Access May 28, 2014

Crystal structure of 2-aminobenzothiazolinium nitrate and theoretical study of the amino-imino tautomerism of 2-aminobenzothiazole

Xingchen Yan, Xiaojing Wu, Jiakun Xu, Yuhua Fan, Caifeng Bi, Xia Zhang, Zhongyu Zhang

Page range: 167-174

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Abstract

2-Aminobenzothiazolinium nitrate ( 1 ) was characterized by elemental analysis, melting point, IR, 1 H NMR, and X-ray crystallography. The driving force for the 2-aminobenzothiazole tautomerism in methanol solution was studied using theoretical calculations. It is suggested that the 2-aminobenzothiazolinium cation is an intermediate product between the amino form ( 2 ) and imino form ( 3 ) of 2-aminobenzothiazole. The tautomerization reaction can proceed in two steps through protonation and deprotonation between the two forms 2 and 3 .

Open Access May 7, 2014

Short and efficient synthesis of 5-aminothiazole-4-carboxamide

Jin Wang, Jianyu Guo, Yihong Tang, Suxia Zhang, Jianwei Tao, Yan Lu

Page range: 175-176

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Abstract

5-Aminothiazole-4-carboxamide is a precursor for the synthesis of thiazole [4,5- d ] pyrimidines. In this work, a new synthesis method with a high total yield (79%) of 5-aminothiazole-4-carboxamide was reported. The starting material is aminocyanacetamide. This synthesis method is environment-friendly and is suitable for industrial production.

Open Access May 12, 2014

The use of diethylene glycol in the synthesis of 2,2′-bibenzimidazole from o-phenylenediamine and oxalic acid

Iwona Mądrzak-Litwa, Aleksandra Borowiak-Resterna

Page range: 177-180

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Abstract

One- and two-step syntheses of 2,2′-bibenzimidazole were compared. Diethylene glycol was used as solvent that provides good solubility of the substrates. The limitation of the one-step preparation is the formation of the by-product, fluoflavine. The two-step synthesis proceeds with the separation of the intermediate product, 1,4-dihydroquinoxaline-2,3-dione, and the final product is only 2,2′-bibenzimidazole. The total yield of the two-step synthesis is above 85%.

Open Access May 28, 2014

Facile one-pot synthesis of chromeno[4,3-b]quinoline derivatives catalyzed by Cu(II)-Schiff base/SBA-15

Radineh Motamedi, Ghasem Rezanejade Bardajee, Somaye Shakeri

Page range: 181-184

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Abstract

A novel, one-pot, simple, environmentally benign and efficient protocol has been employed for the synthesis of chromeno[4,3- b ]quinoline derivatives in the presence of catalytic amounts of Cu(II)-Schiff base/SBA-15 under solvent-free conditions in excellent yields and rates.

Open Access May 12, 2014

5-(2,2-Dimethyl-4H-1,3-benzodioxin)methanol: the synthetic precursor to o-formyl-m-hydroxycinnamic acid, the most oxidized salicylaldehyde-type phytotoxin isolated from rice blast fungus, Magnaporthe grisea

Akihito Saito, Konosuke Hiramatsu, Hai-Qun Cao, Yuta Nagashima, Koji Tanaka, Ayaka Sasaki, Teiko Yamada, Shigefumi Kuwahara, Manabu Nukina, Hiromasa Kiyota

Page range: 185-188

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Abstract

o -Formyl- m -hydroxycinnamic acid, the most oxidized salicylaldehyde-type phytotoxin isolated from rice blast fungus, Magnaporthe grisea , was synthesized for the first time using 5-(2,2-dimethyl-4 H -1,3-benzodioxin)methanol as the starting material, and the proposed structure was confirmed.

About this journal

Heterocyclic Communications is an open-access, peer-reviewed journal committed to publishing preliminary communications, research articles, and reviews on significant developments in all phases of heterocyclic chemistry, including general synthesis, natural products, computational analysis, considerable biological activity and inorganic ring systems.

It is poised to captivate a diverse readership across the fields of chemistry, biology, and biotechnology, including scholars who would like to gain profound insights into the latest scientific breakthroughs, as well as non-scholarly readers, who seek to expand their knowledge and deepen their understanding with reference to the newest discoveries in the field of science.

Heterocyclic Communications assures the top quality of published data through critical peer-review and editorial involvement throughout the entire publication process. Clear presentation of experimental and computational data is strongly emphasized. Thanks to the Open Access model, it also offers unrestricted access to published articles for all users.

The published content includes research articles, review articles, and preliminary communications.

Aims and Scope

The journal aims to facilitate the communication and collaboration of scientists across different countries.

Heterocyclic chemistry is a rapidly growing field. By some estimates original research papers in heterocyclic chemistry have increased to more than 60% of the current organic chemistry literature published. This explosive growth is even greater when considering heterocyclic research published in materials science, physical, biophysical, analytical, bioorganic, pharmaceutical, medicinal and natural products journals. There is a need, therefore, for a journal dedicated explicitly to heterocyclic chemistry and the properties of heterocyclic compounds.

The scope of Heterocyclic Communications is covers scholarly research in:

Development of novel synthetic methods

Significant improvement of known synthetic methods

Chemistry of natural products

Superior biological activity of novel heterocyclic compounds, rational design and synthesis of new drug candidates targeting specific biological receptors

Application of heterocyclic compounds as probes for biomolecules in biophysical and bioanalytical chemistry

Development of new substrates and catalysts in materials chemistry