Open Access Published by De Gruyter

Volume 20 Issue 4

Issue of Heterocyclic Communications

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Contents
Journal Overview

Publicly Available August 5, 2014

Frontmatter

Page range: i-iii

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Preliminary Communication

Open Access August 5, 2014

A novel synthetic approach to 11-substituted dibenzo[b,f][1,4]oxazepines

Nilesh Zaware, Michael Ohlmeyer

Page range: 189-191

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Abstract

A novel protocol for the synthesis of 11-substituted dibenzo[ b , f ][1,4]oxazepines is reported. Seven compounds were designed as analogs of the antipsychotic drug loxapine and antidepressant amoxapine. The key transformations include generation of a carbamate intermediate using phenyl chloroformate which avoids the use of harmful phosgene, a microwave-induced transformation of the carbamate intermediate into various urea derivatives, and a subsequent phosphorous oxychloride-induced cyclocondensation. The simple reactions and wide substrate scope enhance the practical application of this methodology.

Research Articles

Open Access August 5, 2014

Cyclopropyl aziridines: solvolytic reactions of the N-tosylaziridines of (+)-2-carene and (+)-3-carene

Lee J. Silverberg, Javon M. Rabb, Joseph M. Reno, Gang He

Page range: 193-199

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Abstract

The N -tosylaziridine 4 of (+)-2-carene 1 was prepared and subjected to solvolytic reactions with weak protic acids. For comparison, the solvolytic reactions of cis -3-carene- N -tosylaziridine 8 were also studied. The solvolyses of 4 were more rapid than those of 8 , and both rings were opened in 4 , whereas only the aziridine was opened in 8 . This leads to the conclusion that the aziridine and cyclopropane rings in 4 can achieve a conjugated transition state.

Open Access July 3, 2014

Synthesis and crystal structural characterization of two new 3,5-disubstituted 4-amino-1,2,4-triazoles

Xin He, Bin Li, Lang Chen, Xuan Shen, Dun-Ru Zhu

Page range: 201-206

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Abstract

Two new asymmetrical 3-( p -R-phenyl)-4-amino-5-(2-pyridyl)-1,2,4-triazoles ( 3a , R = CH 3 and 3b , R = OCH 3 ) were synthesized with a yield of 58% and 69%, respectively. The compounds 3a and 3b were characterized with FT-IR, 1 H NMR, ESI-MS spectra, and elemental analysis. Additionally, their molecular and crystal structures were determined by single crystal X-ray analysis.

Open Access June 17, 2014

A facile synthesis of 7,12-dihydro-1,3,6,7,12-pentaazapleiadenes by domino reaction

Vishnu Basetti, Rangarao Pallepati, Emima Thadi, Subramanya Hosahalli, Vijay Potluri

Page range: 207-214

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Abstract

Abstract: A tandem strategy for the synthesis of 7,12-dihydro-1,3,6,7,12-pentaazapleiadenes and 4-(2-aminophenoxy)pyrido[4,3- d ]pyrimidin-5(6 H )-ones from readily available starting materials has been developed.

Open Access July 17, 2014

New derivatives of 4,6-dimethylisoxazolo[3,4-b] pyridin-3(1H)-one: synthesis, tautomerism, electronic structure and antibacterial activity

Jarosław Sączewski, Anna Kędzia, Aleksandra Jalińska

Page range: 215-223

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Abstract

The electronic structure and prototropic tautomerism of 4,6-dimethylisoxazolo[3,4- b ]pyridin-3(1 H )-one ( 1 ) were studied theoretically with use of the B3LYP/6-31G* and ωB97X-D/6-31G* density functional methods and SM8 (H 2 O, DMF) solvation models. Compound 1 , which is a weak acid with a p K a of 6.9, undergoes regioselective alkylation and sulfonylation under basic reaction conditions to give a series of N 1-substituted products 2a – i . Later compounds were evaluated in vitro for antibacterial activity with the use of 68 strains of aerobic and anaerobic bacteria, including 12 reference strains.

Open Access August 5, 2014

Synthesis and antimicrobial evaluation of purine substituted N-acyl-α-carboxamides via the Ugi four-component reaction

Gurpreet Kaur, Parul Gupta, Kusum Harjai, Vasundhara Singh

Page range: 225-231

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Abstract

A series of novel purine based N -acyl- α -carboxamides were prepared via the Ugi four-component reaction approach using the pharmacophoric 2-amino-6-chloropurine moiety as the amine component coupled with various aldehydes, carboxylic acids and isocyanides affording a library of multisubstituted compounds 2a–x . These compounds were screened for their antimicrobial activity against Gram negative strains Escherichia coli , Pseudomonas aeruginosa and Gram positive strains Staphylococcus aureus , Staphylococcus epidermidis demonstrating significant biological potency. The best potency for all the strains was found for compound 2x , which is comparable with ampicillin trihydrate as the standard drug.

Open Access June 14, 2014

Facile synthesis of substituted dihydro-1H-pyrazolo[3,4-d]thiazoles through enaminones of 4-thiazolidinones

Poonam Gautam, R. P. Chaudhary

Page range: 233-237

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Abstract

A short two-step synthesis of substituted dihydro-1 H -pyrazolo[3,4- d ]thiazoles from 4-thiazolidinones is described. 4-Thiazolidinones are easily synthesized by the reaction of thiosemicarbazones of carbonyl compounds and chloroacetic acid. Upon treatment with Lawesson’s reagent and dimethylformamide-dimethylacetal, 5-dimethylaminomethylene-3-methylthiazolidine-4-thiones are formed, which undergo condensation with hydrazine derivatives to furnish substituted dihydro-1 H -pyrazolo[3,4- d ]thiazoles. The structure of the synthesized compounds was established by elemental analysis and analysis of spectral data.

Open Access July 4, 2014

Multi-component synthesis of 1,2-diphenyl-2-[2-(5-aryl-6H-1,3,4-thiadiazin-2-yl)hydrazono]ethanone

Tewodros Birhanu Aychiluhim, Rajeswar Rao Vedula

Page range: 239-242

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Abstract

The reaction of thiocarbohydrazide with benzil and a substituted phenacyl bromide provides a facile synthetic route to a 1,2-diphenyl-2-[2-(5-aryl-6 H -1,3,4-thiadiazin-2-yl)hydrazono]ethanone. The synthesized compounds were characterized by spectral and analytical data.

Open Access June 24, 2014

Ab initio study of mechanism of forming a spiro-Si-heterocyclic compound involving Ge from (CH₃)₂Ge=Si: and formaldehyde

Jingjing Ming, Junfeng Han, Xiuhui Lu

Page range: 243-249

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Abstract

(CH 3 ) 2 Ge=Si: and its derivatives (X 2 Ge=Si:, X=H, F, Cl, Br, Ph, Ar) are a new species. Their cycloaddition reaction is a new area for the study of silylene chemistry. The mechanism of the cycloaddition reaction between singlet (CH 3 ) 2 Ge=Si: and formaldehyde was investigated with the CCSD(T)//MP2/6-31G* method. From the potential energy profile, it can be predicted that the reaction has one dominant pathway. The reaction rule presented is that the two reactants first form a four-membered Ge-heterocyclic silylene through the [2+2] cycloaddition reaction. Because of the 3p unoccupied orbital of Si: atom in the four-membered Ge-heterocyclic silylene and the π orbital of formaldehyde forming a π→p donor-acceptor bond, the four-membered Ge-heterocyclic silylene further combines with formaldehyde to form an intermediate product. The Si: atom in the intermediate product is sp 3 hybridized after transition state, and this intermediate isomerizes to a spiro-Si-heterocyclic compound involving Ge via a transition state.

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

Volume 20 Issue 4

Issue of Heterocyclic Communications

Frontmatter

A novel synthetic approach to 11-substituted dibenzo[b,f][1,4]oxazepines

Abstract

Cyclopropyl aziridines: solvolytic reactions of the N-tosylaziridines of (+)-2-carene and (+)-3-carene

Abstract

Synthesis and crystal structural characterization of two new 3,5-disubstituted 4-amino-1,2,4-triazoles

Abstract

A facile synthesis of 7,12-dihydro-1,3,6,7,12-pentaazapleiadenes by domino reaction

Abstract

New derivatives of 4,6-dimethylisoxazolo[3,4-b] pyridin-3(1H)-one: synthesis, tautomerism, electronic structure and antibacterial activity

Abstract

Synthesis and antimicrobial evaluation of purine substituted N-acyl-α-carboxamides via the Ugi four-component reaction

Abstract

Facile synthesis of substituted dihydro-1H-pyrazolo[3,4-d]thiazoles through enaminones of 4-thiazolidinones

Abstract

Multi-component synthesis of 1,2-diphenyl-2-[2-(5-aryl-6H-1,3,4-thiadiazin-2-yl)hydrazono]ethanone

Abstract

Ab initio study of mechanism of forming a spiro-Si-heterocyclic compound involving Ge from (CH3)2Ge=Si: and formaldehyde

Abstract

Ab initio study of mechanism of forming a spiro-Si-heterocyclic compound involving Ge from (CH₃)₂Ge=Si: and formaldehyde