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Advances in Heterocyclic Chemistry
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Advances in Heterocyclic Chemistry

A special issue of Molecules (ISSN 1420-3049).

Deadline for manuscript submissions: closed (30 September 2010) | Viewed by 107940

Special Issue Editor

Prof. Dr. Norbert Haider

E-Mail Website
Guest Editor
Department of Pharmaceutical Chemistry, University of Vienna, Althanstrasse 14, 1090 Vienna, Austria
Interests: medicinal heterocyclic chemistry; pyridazines; carbazoles; nitrogen hetarenes

Special Issue Information

Dear Colleagues,

This special issue is dedicated to the publication of the latest research results in the field of Heterocyclic Chemistry, especially focusing on the synthesis, reactivity, structure, and biological activity of heterocyclic compounds.

Prof. Dr. Norbert Haider
Guest Editor

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Published Papers (10 papers)

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Research

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207 KiB  
Article
Drug Resistance Modulation in Staphylococcus Aureus, a New Biological Activity for Mesoionic Hydrochloride Compounds
by Cledualdo Soares de Oliveira, Vivyanne Dos Santos Falcão-Silva, José Pinto Siqueira-Júnior, David Peter Harding, Bruno Freitas Lira, Jorge Gonçalo Fernandes Lorenzo, José Maria Barbosa-Filho and Petrônio Filgueiras de Athayde-Filho
Molecules 2011, 16(3), 2023-2031; https://doi.org/10.3390/molecules16032023 - 28 Feb 2011
Cited by 21 | Viewed by 9146
Abstract
Two salts of the mesoionic compounds 1,4-diphenyl-5-(5-nitro-2-furanyl)-1,3,4-thiadiazolium-2-thiol chloride (MC-1) and 4-phenyl-5-(5-nitro-2-furanyl)-1,3,4-thiadiazolium-2-phenylamine chloride (MC-2) were synthesized utilizing 1,4-diphenyl-thiosemicarbazide and 5-nitro-2-furoyl chloride as starting materials. Their structures were characterized by IR, 1H-NMR, 13C-NMR and elemental analysis. These compounds were [...] Read more.
Two salts of the mesoionic compounds 1,4-diphenyl-5-(5-nitro-2-furanyl)-1,3,4-thiadiazolium-2-thiol chloride (MC-1) and 4-phenyl-5-(5-nitro-2-furanyl)-1,3,4-thiadiazolium-2-phenylamine chloride (MC-2) were synthesized utilizing 1,4-diphenyl-thiosemicarbazide and 5-nitro-2-furoyl chloride as starting materials. Their structures were characterized by IR, 1H-NMR, 13C-NMR and elemental analysis. These compounds were analyzed for their influence on the effectiveness of norfloxacin, tetracycline, and erythromycin (standard antibiotics) against resistant strains of Staphylococcus aureus. MC-1 and MC-2, at sub-inhibitory concentrations of 16 μg/mL, favourably modulated the antibiotic activity of tetracycline by 16- and 32-fold, respectively (MIC), and that of erythromycin by 4-fold. Full article
(This article belongs to the Special Issue Advances in Heterocyclic Chemistry)
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158 KiB  
Article
Chemistry of the Enaminone of 1-Acetylnaphthalene under Microwave Irradiation Using Chitosan as a Green Catalyst
by Huwaida M. E. Hassaneen
Molecules 2011, 16(1), 609-623; https://doi.org/10.3390/molecules16010609 - 17 Jan 2011
Cited by 19 | Viewed by 8915
Abstract
Enaminone 1 was reacted with hydrazonoyl halides 2a-d to yield 3,4-disubstituted pyrazoles 6a-d. Coupling with arenediazonium chlorides afforded the 2-(arylhydrazono)-3-(1-naphthalenyl)-3-oxopropionaldehydes 13a-c. Compounds 13 could be utilized for the synthesis of a variety of arylpyrazoles, arylazolopyrimidines, and pyridazinones via reaction with hydrazines, [...] Read more.
Enaminone 1 was reacted with hydrazonoyl halides 2a-d to yield 3,4-disubstituted pyrazoles 6a-d. Coupling with arenediazonium chlorides afforded the 2-(arylhydrazono)-3-(1-naphthalenyl)-3-oxopropionaldehydes 13a-c. Compounds 13 could be utilized for the synthesis of a variety of arylpyrazoles, arylazolopyrimidines, and pyridazinones via reaction with hydrazines, aminoazoles, and active methylene derivatives, respectively. A comparative study of aforementioned reactions was carried out with chitosan as a basic ecofriendly catalyst under conventional heating as well as under pressurized microwave irradiation conditions. Full article
(This article belongs to the Special Issue Advances in Heterocyclic Chemistry)
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197 KiB  
Article
Heterocyclic Analogues of Xanthone and Xanthione. 1H-Pyrano[2,3-c:6,5-c]dipyrazol-4(7H)-ones and Thiones: Synthesis and NMR Data
by Barbara Datterl, Nicole Tröstner, Dorota Kucharski and Wolfgang Holzer
Molecules 2010, 15(9), 6106-6126; https://doi.org/10.3390/molecules15096106 - 1 Sep 2010
Cited by 20 | Viewed by 8380
Abstract
The synthesis of the title compounds is described. Reaction of 1-substituted 2-pyrazolin-5-ones with 5-chloro-1-phenyl-1H-pyrazole-4-carbonyl chloride or 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbonyl chloride, respectively, using calcium hydroxide in refluxing 1,4-dioxane gave the corresponding 4-heteroaroylpyrazol-5-ols, which were cyclized into 1H-pyrano[2,3-c:6,5-c]dipyrazol-4(7H)-ones by treatment with K2CO3/DMF. The latter were converted into [...] Read more.
The synthesis of the title compounds is described. Reaction of 1-substituted 2-pyrazolin-5-ones with 5-chloro-1-phenyl-1H-pyrazole-4-carbonyl chloride or 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbonyl chloride, respectively, using calcium hydroxide in refluxing 1,4-dioxane gave the corresponding 4-heteroaroylpyrazol-5-ols, which were cyclized into 1H-pyrano[2,3-c:6,5-c]dipyrazol-4(7H)-ones by treatment with K2CO3/DMF. The latter were converted into the corresponding thiones upon reaction with Lawesson’s reagent. Detailed NMR spectroscopic investigations (1H, 13C, 15N) of the ring systems and their precursors are presented. Full article
(This article belongs to the Special Issue Advances in Heterocyclic Chemistry)
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121 KiB  
Article
Enhanced Reactivity of [Hydroxy(tosyloxy)iodo]benzene in Fluoroalcohol Media. Efficient Direct Synthesis of Thienyl(aryl)iodonium Salts
by Motoki Ito, Chieko Ogawa, Nobutaka Yamaoka, Hiromichi Fujioka, Toshifumi Dohi and Yasuyuki Kita
Molecules 2010, 15(3), 1918-1931; https://doi.org/10.3390/molecules15031918 - 17 Mar 2010
Cited by 40 | Viewed by 8099
Abstract
In this manuscript, we report clear evidence for the generation of aromatic cation radicals produced by using [hydroxy(tosyloxy)iodo]benzene (HTIB) in fluoroalcohol solvents such as 2,2,2-trifluoroethanol (TFE) and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP). The single-electron-transfer (SET) oxidation ability of HTIB to give cation radicals was first established [...] Read more.
In this manuscript, we report clear evidence for the generation of aromatic cation radicals produced by using [hydroxy(tosyloxy)iodo]benzene (HTIB) in fluoroalcohol solvents such as 2,2,2-trifluoroethanol (TFE) and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP). The single-electron-transfer (SET) oxidation ability of HTIB to give cation radicals was first established by ESR and UV measurements. The reaction was broadly applied to various thiophenes, and unique thienyliodonium salts were directly synthesized by this method in excellent yields without the production of any harmful byproducts. Full article
(This article belongs to the Special Issue Advances in Heterocyclic Chemistry)
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213 KiB  
Article
Heterocyclic Analogs of Thioflavones: Synthesis and NMR Spectroscopic Investigations
by Ferdinand C. Fuchs, Gernot A. Eller and Wolfgang Holzer
Molecules 2009, 14(9), 3814-3832; https://doi.org/10.3390/molecules14093814 - 25 Sep 2009
Cited by 40 | Viewed by 11213
Abstract
The synthesis of several hitherto unknown heterocyclic ring systems derived from thioflavone is described. Coupling of various o-haloheteroarenecarbonyl chlorides with phenylacetylene gives 1-(o-haloheteroaryl)-3-phenylprop-2-yn-1-ones, which were treated with NaSH in refluxing ethanol to yield the corresponding bi- and tricyclic annelated 2-phenylthiopyran-4-ones. [...] Read more.
The synthesis of several hitherto unknown heterocyclic ring systems derived from thioflavone is described. Coupling of various o-haloheteroarenecarbonyl chlorides with phenylacetylene gives 1-(o-haloheteroaryl)-3-phenylprop-2-yn-1-ones, which were treated with NaSH in refluxing ethanol to yield the corresponding bi- and tricyclic annelated 2-phenylthiopyran-4-ones. Detailed NMR spectroscopic investigations of the ring systems and their precursors are presented. Full article
(This article belongs to the Special Issue Advances in Heterocyclic Chemistry)
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222 KiB  
Communication
Synthesis, ex Vivo and in Vitro Hydrolysis Study of an Indoline Derivative Designed as an Anti-Inflammatory with Reduced Gastric Ulceration Properties
by Man Chin Chung, Jean Leandro Dos Santos, Ednir Vizioli Oliveira, Lorena Blau, Renato Farina Menegon and Rosângela Gonçalves Peccinini
Molecules 2009, 14(9), 3187-3197; https://doi.org/10.3390/molecules14093187 - 26 Aug 2009
Cited by 16 | Viewed by 13703
Abstract
The compound 1-(2,6-dichlorophenyl)indolin-2-one (1), planned as a pro-drug of diclofenac (2), was easily synthesized in 94% yield by an intramolecular reaction in the presence of coupling agent (i.e., EDC). Compound 1 showed anti-inflammatory and analgesic activity without gastro-ulcerogenic effects. The chemical [...] Read more.
The compound 1-(2,6-dichlorophenyl)indolin-2-one (1), planned as a pro-drug of diclofenac (2), was easily synthesized in 94% yield by an intramolecular reaction in the presence of coupling agent (i.e., EDC). Compound 1 showed anti-inflammatory and analgesic activity without gastro-ulcerogenic effects. The chemical and enzymatic hydrolysis profile of the lactam derivative 1 does not indicate conversion to diclofenac (2). This compound is a new non-ulcerogenic prototype for treatment of chronic inflammatory diseases. Full article
(This article belongs to the Special Issue Advances in Heterocyclic Chemistry)
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138 KiB  
Article
The Reaction of 4,5-Dichloro-1,2,3-dithiazolium Chloride with Sulfimides: A New Synthesis of N-Aryl-1,2,3-dithiazolimines
by Andreas S. Kalogirou and Panayiotis A. Koutentis
Molecules 2009, 14(7), 2356-2362; https://doi.org/10.3390/molecules14072356 - 2 Jul 2009
Cited by 6 | Viewed by 11748
Abstract
N-Aryl-S,S-dimethylsulfimides 3(Ar = 4-NO2C6H4), 4 (Ar = Ph) and 5 (Ar = 4-Tol)react with Appel salt 1 to give the corresponding N-aryl-(4-chloro-5H-1,2,3-dithiazolylidene)benzenamines 8 (Ar = 4-NO2C6 [...] Read more.
N-Aryl-S,S-dimethylsulfimides 3(Ar = 4-NO2C6H4), 4 (Ar = Ph) and 5 (Ar = 4-Tol)react with Appel salt 1 to give the corresponding N-aryl-(4-chloro-5H-1,2,3-dithiazolylidene)benzenamines 8 (Ar = 4-NO2C6H4), 9 (Ar = Ph) and 10 (Ar = 4-Tol) in 84, 94 and 87% yields, respectively. The reaction proceeds in the absence of base and a proposed reaction mechanism is given. Full article
(This article belongs to the Special Issue Advances in Heterocyclic Chemistry)
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Review

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406 KiB  
Review
Recent Advance in Heterocyclic Organozinc and Organomanganese Compounds; Direct Synthetic Routes and Application in Organic Synthesis
by Seung-Hoi Kim and Reuben D. Rieke
Molecules 2010, 15(11), 8006-8038; https://doi.org/10.3390/molecules15118006 - 8 Nov 2010
Cited by 14 | Viewed by 11963
Abstract
A practical synthetic route for the preparation of 2-pyridyl and 3-pyridyl derivatives has been accomplished by utilizing a simple coupling reaction of stable 2-pyridylzinc bromides and 3-pyridylzinc bromides. The organozincs used in this study were easily prepared via the direct insertion of active [...] Read more.
A practical synthetic route for the preparation of 2-pyridyl and 3-pyridyl derivatives has been accomplished by utilizing a simple coupling reaction of stable 2-pyridylzinc bromides and 3-pyridylzinc bromides. The organozincs used in this study were easily prepared via the direct insertion of active zinc into the corresponding bromopyridines. The subsequent coupling reactions with a variety of different electrophiles have afforded the corresponding coupling products. Using highly active manganese, a variety of Grignard-type organomanganese reagents have been obtained. The subsequent coupling reactions of the resulting organomanganese reagents with several electrophiles have also been accomplished under mild conditions. Full article
(This article belongs to the Special Issue Advances in Heterocyclic Chemistry)
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1784 KiB  
Review
Chemistry of Nitroquinolones and Synthetic Application to Unnatural 1-Methyl-2-quinolone Derivatives
by Nagatoshi Nishiwaki
Molecules 2010, 15(8), 5174-5195; https://doi.org/10.3390/molecules15085174 - 30 Jul 2010
Cited by 19 | Viewed by 11766
Abstract
The 1-methyl-2-quinolone (MeQone) framework is often found in alkaloids and recently attention was drawn to unnatural MeQone derivatives with the aim of finding new biologically active compounds, however, low reactivity of the MeQone framework prevents the syntheses of versatile derivatives. A nitro group [...] Read more.
The 1-methyl-2-quinolone (MeQone) framework is often found in alkaloids and recently attention was drawn to unnatural MeQone derivatives with the aim of finding new biologically active compounds, however, low reactivity of the MeQone framework prevents the syntheses of versatile derivatives. A nitro group is one of the useful activating groups for this framework that enables a concise chemical transformation. Among nitroquinolones, 1-methyl-3,6,8-trinitro-2-quinolone (TNQ) exhibits unusual reactivity favoring region-selective cine-substitutions that afford 4-substituted 1-methyl-6,8-dinitro-2-quinolones upon treatment with nucleophilic reagents. Contrary to this, 1-methyl-3,6-dinitro-2-quinolone (3,6-DNQ) does not undergo any reaction under the same conditions. The unusual reactivity of TNQ is caused by steric repulsion between the methyl group at the 1-position and the nitro group at the 8-position, which distorts the MeQone framework. As a result, the pyridone ring of TNQ loses aromaticity and acts rather as an activated nitroalkene. Indeed, the pyridone moiety of TNQ undergoes cycloaddition with electron-rich alkenes or dienes under mild conditions, whereby a new fused ring is constructed on the [c]-face of the MeQone. Consequently, TNQ can be used as a new scaffold leading to versatile unnatural MeQone derivatives. Full article
(This article belongs to the Special Issue Advances in Heterocyclic Chemistry)
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232 KiB  
Review
Reactivity and Synthetic Applications of 4,5-Dicyanopyridazine: An Overview
by Renzo Alfini, Marco Cecchi and Donatella Giomi
Molecules 2010, 15(3), 1722-1745; https://doi.org/10.3390/molecules15031722 - 12 Mar 2010
Cited by 13 | Viewed by 11473
Abstract
Despite the poor reputation of electron-deficient pyridazines in intermolecular Hetero Diels-Alder (HDA) reactions, 4,5-dicyanopyridazine (DCP) showed a surprising reactivity as a heterocyclic azadiene in inverse electron-demand HDA processes with different dienophiles. The use of alkenes, alkynes and enamines as 2p electron counterparts afforded [...] Read more.
Despite the poor reputation of electron-deficient pyridazines in intermolecular Hetero Diels-Alder (HDA) reactions, 4,5-dicyanopyridazine (DCP) showed a surprising reactivity as a heterocyclic azadiene in inverse electron-demand HDA processes with different dienophiles. The use of alkenes, alkynes and enamines as 2p electron counterparts afforded dicyanocyclohexa-1,3-dienes and substituted phthalonitriles, respectively, while the use of suitable bis-dienophiles provides a general strategy for the one-pot synthesis of polycyclic carbo- and hetero-cage systemsthrough pericyclic three-step homodomino processes. HDA reactions with heterocyclic dienophiles allowed direct benzoannelation: in particular, pyrrole and indole derivatives were converted to dicyano-indoles and -carbazoles. In addition an unprecedented reactivity of DCP as a very reactive heterocyclic electrophile at the C-4 carbon was also evidenced: by changing the experimental conditions, cyanopyrrolyl- and cyanoindolyl-pyridazines were obtained through reactions of pyrrole and indole systems as carbon nucleophiles in formal SNAr2 processes where a CN group of DCP acts as leaving group. Thus, careful control of the reaction conditions allows exploitation of both pathways for the synthesis of different classes of heterocyclic derivatives. Full article
(This article belongs to the Special Issue Advances in Heterocyclic Chemistry)
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