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Special Issue "Hypervalent Iodine"

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

Deadline for manuscript submissions: closed (30 June 2004)

Special Issue Editor

Guest Editor
Dr. Antigoni Kotali

Lab. of Organic Chemistry Depr. of Chemical Engineering University of Thessaloniki Thessaloniki GR-54124
Phone: +00302310996253

Published Papers (18 papers)

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Editorial

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Open AccessEditorial Hypervalent Iodine
Molecules 2005, 10(1), 181-182; doi:10.3390/10010181
Received: 9 July 2004 / Published: 31 January 2005
PDF Full-text (98 KB) | HTML Full-text | XML Full-text
(This article belongs to the Special Issue Hypervalent Iodine)

Research

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Open AccessArticle Synthesis of Unsymmetrical Annulated 2,2’-Bipyridine Analogues with Attached Cycloalkene and Piperidine Rings via Sequential Diels-Alder Reaction of 5,5’-bi-1,2,4-triazines†
Molecules 2005, 10(1), 265-273; doi:10.3390/10010265
Received: 5 September 2004 / Accepted: 22 September 2004 / Published: 31 December 2005
Cited by 14 | PDF Full-text (215 KB) | HTML Full-text | XML Full-text
Abstract
Synthesis of bisfunctionalized unsymmetrical 2,2’-bipyridines 8 or their sulfonyl derivatives 12a,b are described. They were prepared via the Diels-Alder reaction of 1-methyl-4-pyrrolidin-1-yl-1,2,3,6-tetrahydropyridine (6) with 3,3’-bis(methyl- sulfanyl)-5,5’-bi-1,2,4-triazine (1). The reaction leads to the single cycloaddition product 7 which undergoes Diels-Alder reaction with cyclic [...] Read more.
Synthesis of bisfunctionalized unsymmetrical 2,2’-bipyridines 8 or their sulfonyl derivatives 12a,b are described. They were prepared via the Diels-Alder reaction of 1-methyl-4-pyrrolidin-1-yl-1,2,3,6-tetrahydropyridine (6) with 3,3’-bis(methyl- sulfanyl)-5,5’-bi-1,2,4-triazine (1). The reaction leads to the single cycloaddition product 7 which undergoes Diels-Alder reaction with cyclic enamines 2a,b to give unsymmetrical 2,2’-bipyridine derivatives 8, consisting of the two different heterocyclic units: cycloalkeno[c]pyridine and 2,6-naphthyridine. Full article
(This article belongs to the Special Issue Hypervalent Iodine)
Open AccessArticle Stereoselective Synthesis of 5-7 membered Cyclic Ethers by Deiodonative Ring-Enlargement Using Hypervalent Iodine Reagents
Molecules 2005, 10(1), 183-189; doi:10.3390/10010183
Received: 19 April 2004 / Revised: 15 January 1995 / Accepted: 1 July 2004 / Published: 31 January 2005
Cited by 13 | PDF Full-text (212 KB) | HTML Full-text | XML Full-text
Abstract
Stereoselective synthesis of 5-7 membered cyclic ethers was achieved by deiodonative ring-enlargement of cyclic ethers having an iodoalkyl substituent. The reaction took place readily under mild conditions using hypervalent iodine compounds and an acetoxy or a trifluoroacetoxy group was introduced into the [...] Read more.
Stereoselective synthesis of 5-7 membered cyclic ethers was achieved by deiodonative ring-enlargement of cyclic ethers having an iodoalkyl substituent. The reaction took place readily under mild conditions using hypervalent iodine compounds and an acetoxy or a trifluoroacetoxy group was introduced into the rings depending on the hypervalent iodine reagent employed. The use of hexafluoroisopropanol (HFIP) as solvent is critical. Full article
(This article belongs to the Special Issue Hypervalent Iodine)
Open AccessArticle Easy and Safe Preparations of (Diacetoxyiodo) arenes from Iodoarenes, with Urea-Hydrogen Peroxide Adduct (UHP) as the Oxidant and the Fully Interpreted 1H- and 13C-NMR Spectra of the Products
Molecules 2005, 10(1), 190-194; doi:10.3390/10010190
Received: 30 April 2004 / Revised: 12 January 2005 / Accepted: 13 January 2005 / Published: 31 January 2005
Cited by 7 | PDF Full-text (154 KB) | HTML Full-text | XML Full-text
Abstract
An easy and safe, though only moderately effective method is presented forpreparing (diacetoxyiodo)arenes, ArI(OAc)2, from iodoarenes, ArI, using thecommercially available and easily handled urea-hydrogen peroxide adduct (UHP) as theoxidant. The reactions take place in anhydrous AcOH/Ac2O/AcONa (a catalyst)mixtures, at 40 oC for [...] Read more.
An easy and safe, though only moderately effective method is presented forpreparing (diacetoxyiodo)arenes, ArI(OAc)2, from iodoarenes, ArI, using thecommercially available and easily handled urea-hydrogen peroxide adduct (UHP) as theoxidant. The reactions take place in anhydrous AcOH/Ac2O/AcONa (a catalyst)mixtures, at 40 oC for 3.5 h to afford the purified ArI(OAc)2 in 37-78% yields. The fullyinterpreted 1H- and 13C-NMR spectra of the ArI(OAc)2 products are reported. Full article
(This article belongs to the Special Issue Hypervalent Iodine)
Open AccessArticle Addition to Electron Deficient Olefins of α-Oxy Carbon- Centered Radicals, Generated from Cyclic Ethers and Acetals by the Reaction with Alkylperoxy- λ3-iodane
Molecules 2005, 10(1), 195-200; doi:10.3390/10010195
Received: 11 May 2004 / Revised: 24 November 2004 / Accepted: 25 November 2004 / Published: 31 January 2005
Cited by 7 | PDF Full-text (216 KB) | HTML Full-text | XML Full-text
Abstract Thermal decomposition of 1-tert-butylperoxy-1,2-benziodoxol-3(1H)-one in cyclic ethers and acetals at 50 °C generates α-oxy carbon-centered radicals, which undergo an addition reaction with vinyl sulfones and unsaturated esters. Full article
(This article belongs to the Special Issue Hypervalent Iodine)
Open AccessArticle Oxidative Dearomatization of Phenols and Anilines via λ3- and λ5-Iodane-Mediated Phenylation and Oxygenation
Molecules 2005, 10(1), 201-216; doi:10.3390/10010201
Received: 28 May 2004 / Accepted: 25 July 2004 / Published: 31 January 2005
Cited by 30 | PDF Full-text (291 KB) | HTML Full-text | XML Full-text
Abstract
Treatment of 2-methylphenols with chloro(diphenyl)-λ3-iodane led to theirregioselective dearomatizing 2-phenylation into cyclohexa-2,4-dienone derivatives via aproposed ligand coupling reaction. In the same vein of investigation, treatment of2-methylanilines with the λ5-iodane 2-iodoxybenzoic acid IBX reagent led to theirregioselective dearomatization into [...] Read more.
Treatment of 2-methylphenols with chloro(diphenyl)-λ3-iodane led to theirregioselective dearomatizing 2-phenylation into cyclohexa-2,4-dienone derivatives via aproposed ligand coupling reaction. In the same vein of investigation, treatment of2-methylanilines with the λ5-iodane 2-iodoxybenzoic acid IBX reagent led to theirregioselective dearomatization into previously undescribed ortho-quinol imines. Full article
(This article belongs to the Special Issue Hypervalent Iodine)
Open AccessArticle Application of [Hydroxy(tosyloxy)iodo]benzene in the Wittig-Ring Expansion Sequence for the Synthesis of β-Benzocyclo-alkenones from α-Benzocycloalkenones
Molecules 2005, 10(1), 217-225; doi:10.3390/10010217
Received: 5 July 2004 / Accepted: 14 July 2004 / Published: 31 January 2005
Cited by 27 | PDF Full-text (209 KB) | HTML Full-text | XML Full-text
Abstract
The conversion of α-benzocycloalkenones to homologous β-benzocyclo-alkenones containing six, seven and eight-membered rings is reported. This wasaccomplished via a Wittig olefination-oxidative rearrangement sequence using[hydroxy(tosyloxy)iodo]-benzene (HTIB) is the oxidant, that enables the synthesis ofregioisomeric pairs of methyl-substituted β-benzocycloalkenones. The incorporation ofcarbon-13 at C-1 [...] Read more.
The conversion of α-benzocycloalkenones to homologous β-benzocyclo-alkenones containing six, seven and eight-membered rings is reported. This wasaccomplished via a Wittig olefination-oxidative rearrangement sequence using[hydroxy(tosyloxy)iodo]-benzene (HTIB) is the oxidant, that enables the synthesis ofregioisomeric pairs of methyl-substituted β-benzocycloalkenones. The incorporation ofcarbon-13 at C-1 of the β-tetralone nucleus was also demonstrated. The Wittig-HTIBapproach is a useful alternative to analogous sequences in which Tl(NO3)3·3H2O or thePrevost combination (AgNO3/I2) are employed in the oxidation step. Full article
(This article belongs to the Special Issue Hypervalent Iodine)
Open AccessArticle A Survey on the Reactivity of Phenyliodonium Ylide of 2-Hydroxy-1,4-Naphthoquinone with Amino Compounds
Molecules 2005, 10(1), 226-237; doi:10.3390/10010226
Received: 1 August 2004 / Accepted: 13 September 2004 / Published: 31 January 2005
Cited by 10 | PDF Full-text (236 KB) | HTML Full-text | XML Full-text
Abstract
The phenyliodonium ylide of 2-hydroxy-1,4-naphthoquinone reacts with aminoesters, ureas, aminoalcohols and aminophenols in refluxing dichloromethane to afford good yields of indanedione 2-carboxamido compounds, that in solution exist in an enol-amide form. The same reactants in a copper-catalyzed reaction afford mainly the corresponding [...] Read more.
The phenyliodonium ylide of 2-hydroxy-1,4-naphthoquinone reacts with aminoesters, ureas, aminoalcohols and aminophenols in refluxing dichloromethane to afford good yields of indanedione 2-carboxamido compounds, that in solution exist in an enol-amide form. The same reactants in a copper-catalyzed reaction afford mainly the corresponding N-arylo compounds. Arylhydrazines are mainly oxidized by the ylide and arylation occurs only in a low yield. Full article
(This article belongs to the Special Issue Hypervalent Iodine)
Open AccessArticle Pd-Catalyzed Carbonyl Insertion Coupling Reactions of a Hypervalent Iodoheterocycle with Alcohols and Amines
Molecules 2005, 10(1), 238-243; doi:10.3390/10010238
Received: 17 August 2004 / Accepted: 15 September 2004 / Published: 31 January 2005
PDF Full-text (170 KB) | HTML Full-text | XML Full-text
Abstract The palladium-catalyzed cross-coupling carbonyl insertion reaction between 3,7-bis(N,N-dimethylamino)-10H-dibenz[b,e]iodinium iodide (1) and alcohols or amines 2 is described. Some new amides and esters 3 containing an active iodo functional group have been prepared in 65-91% yields. Full article
(This article belongs to the Special Issue Hypervalent Iodine)
Open AccessArticle Substrate Dependence in Aqueous Diels-Alder Reactions of Cyclohexadiene Derivatives with 1,4-Benzoquinone
Molecules 2005, 10(1), 244-250; doi:10.3390/10010244
Received: 10 May 2004 / Revised: 25 November 2004 / Accepted: 25 November 2004 / Published: 31 January 2005
Cited by 5 | PDF Full-text (200 KB) | HTML Full-text | XML Full-text
Abstract
A reactivity difference based on the position of substituents on cyclohexa-1,3- diene was observed for the title reaction. The effect of water as solvent was more distinct for 1-methyl-4-isopropylcyclohexa-1,3-diene than for 2-methyl-5-isopropylcyclohexa- 1,3-diene or non-substituted cyclohexa-1,3-diene. The effect of NaCl (salting-out) and [...] Read more.
A reactivity difference based on the position of substituents on cyclohexa-1,3- diene was observed for the title reaction. The effect of water as solvent was more distinct for 1-methyl-4-isopropylcyclohexa-1,3-diene than for 2-methyl-5-isopropylcyclohexa- 1,3-diene or non-substituted cyclohexa-1,3-diene. The effect of NaCl (salting-out) and guanidium chloride (salting-in) was also large for 1-methyl-4-isopropylcyclohexa-1,3- diene. Full article
(This article belongs to the Special Issue Hypervalent Iodine)
Open AccessArticle Synthesis and Molecular Structure of Methyl 4-O-methyl-α-D-glucopyranuronate
Molecules 2005, 10(1), 251-258; doi:10.3390/10010251
Received: 17 August 2004 / Revised: 22 November 2004 / Accepted: 23 November 2004 / Published: 31 January 2005
Cited by 11 | PDF Full-text (268 KB) | HTML Full-text | XML Full-text
Abstract A method for the preparation of methyl 4-O-methyl-α-D-glucopyranuronate andits single crystal X-ray structure determination are reported. The molecule adopts an almostideal 4C1 (OC3) conformation. Full article
(This article belongs to the Special Issue Hypervalent Iodine)
Open AccessArticle Synthesis of the Key Precursor of Hirsutellide A
Molecules 2005, 10(1), 259-264; doi:10.3390/10010259
Received: 27 February 2004 / Accepted: 19 March 2004 / Published: 31 January 2005
Cited by 7 | PDF Full-text (183 KB) | HTML Full-text | XML Full-text
Abstract Hexadepsipeptide 2, the precursor of Hirsutellide A (1), was synthesized in an overall yield of 45% from N-Boc-Me-Gly via three coupling reactions using dicyclohexylcarbodiimide (DCC), O-(7-azabenzotriazol-1-yl)-N,N,N’,N’-tetramethyl- uronium hexafluorophosphate (HATU) and bis(2-oxo-3-oxazolidinyl)phosphinic chloride (BOP-Cl), respectively. Full article
(This article belongs to the Special Issue Hypervalent Iodine)
Open AccessArticle A Direct Route to 6,6’-Disubstituted-2,2’-Bipyridines by Double Diels-Alder/retro Diels-Alder Reaction of 5,5’-bi-1,2,4-Triazines
Molecules 2005, 10(1), 274-278; doi:10.3390/10010274
Received: 5 September 2004 / Revised: 3 January 2005 / Accepted: 3 January 2005 / Published: 31 January 2005
Cited by 7 | PDF Full-text (177 KB) | HTML Full-text | XML Full-text
Abstract Inverse electron demand Diels-Alder reaction of functionalized 5,5’-bi-1,2,4- triazines with bicyclo[2.2.1]hepta-2,5-diene in boiling p-cymene leads to a range of 6,6’- disubstituted-2,2’-bipyridines in good yield. Full article
(This article belongs to the Special Issue Hypervalent Iodine)
Open AccessArticle Chemical and Photochemical Synthesis of Substituted Dihydro-thieno[2',3':4,5]thieno[2,3-c]quinolin-6-ones and Tetrahydro-dithieno[2,3-b:2',3'-d]thieno[2'',3''c:2'',3''c’]diquinolin-6,14-dione
Molecules 2005, 10(1), 279-288; doi:10.3390/10010279
Received: 28 September 2004 / Revised: 2 November 2004 / Accepted: 30 December 2004 / Published: 31 January 2005
Cited by 4 | PDF Full-text (206 KB) | HTML Full-text | XML Full-text
Abstract
Some new substituted dihydrothieno[2',3':4,5]thieno[2,3-c]quinolin-6-ones 9- 12 and tetrahydrodithieno[2,3-b: 2',3'-d]thieno[2'',3''-c:2'',3''-c’]diquinolin-6,14-dione (17) were prepared from the corresponding new anilides 5-8 and from the corresponding dianilide 15, respectively, by a multistep combination of chemical and photochemical reactions. All the prepared compounds are of particular interest [...] Read more.
Some new substituted dihydrothieno[2',3':4,5]thieno[2,3-c]quinolin-6-ones 9- 12 and tetrahydrodithieno[2,3-b: 2',3'-d]thieno[2'',3''-c:2'',3''-c’]diquinolin-6,14-dione (17) were prepared from the corresponding new anilides 5-8 and from the corresponding dianilide 15, respectively, by a multistep combination of chemical and photochemical reactions. All the prepared compounds are of particular interest because they might serve as DNA intercalators in anticancer therapy. Full article
(This article belongs to the Special Issue Hypervalent Iodine)
Open AccessArticle An Electron Transfer Approach to the Preparation of Highly Functionalized Anthraquinones
Molecules 2005, 10(1), 289-294; doi:10.3390/10010289
Received: 24 August 2004 / Accepted: 23 September 2004 / Published: 31 January 2005
Cited by 3 | PDF Full-text (188 KB) | HTML Full-text | XML Full-text
Abstract A series of highly functionalized quinones was prepared by an original reaction of 2,3-bis(chloromethyl)-1,4-dimethoxyanthraquinone (6) with various nitronate anions under electron transfer reaction conditions. Full article
(This article belongs to the Special Issue Hypervalent Iodine)
Open AccessArticle Synthesis of Analogs of Amathamide A and Their Preliminary Antimicrobial Activity
Molecules 2005, 10(1), 295-301; doi:10.3390/10010295
Received: 20 August 2004 / Revised: 6 January 2005 / Accepted: 7 January 2005 / Published: 31 January 2005
Cited by 3 | PDF Full-text (171 KB) | HTML Full-text | XML Full-text
Abstract
Syntheses of three non-brominated analogs of amathamide A (1), a natural alkaloid isolated from the Tasmanian marine bryozoan Amathia wilsoni, are described. Antimicrobial activity against Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Pseudomona aeruginosa, and Candida albicans was tested. Test results for amathamide [...] Read more.
Syntheses of three non-brominated analogs of amathamide A (1), a natural alkaloid isolated from the Tasmanian marine bryozoan Amathia wilsoni, are described. Antimicrobial activity against Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Pseudomona aeruginosa, and Candida albicans was tested. Test results for amathamide A (1) showed a weak activity against C. albicans and E. coli. The three non-natural analogs 2-4 proved to be inactive compounds. Full article
(This article belongs to the Special Issue Hypervalent Iodine)
Open AccessArticle Syntheses, Characterization and Study of the Use of Cobalt (II) Schiff–Base Complexes as Catalysts for the Oxidation of Styrene by Molecular Oxygen
Molecules 2005, 10(1), 302-311; doi:10.3390/10010302
Received: 13 August 2004 / Accepted: 14 September 2005 / Published: 31 January 2005
Cited by 23 | PDF Full-text (349 KB) | HTML Full-text | XML Full-text
Abstract
Schiff-Base complexes of bis-5-phenylazosalicylaldehyde ethylenediimine and bis-5-phenylazosalicylaldehyde-O-phenylenediimine ligands with Co(II) (I and II) have been synthesized and characterized by their IR spectra and elemental analyses. These complexes catalyze the oxidation of styrene in the presence of dioxygen and excess pyridine. The effect [...] Read more.
Schiff-Base complexes of bis-5-phenylazosalicylaldehyde ethylenediimine and bis-5-phenylazosalicylaldehyde-O-phenylenediimine ligands with Co(II) (I and II) have been synthesized and characterized by their IR spectra and elemental analyses. These complexes catalyze the oxidation of styrene in the presence of dioxygen and excess pyridine. The effect of the reaction conditions on the oxidation of styrene was studied by varying solvent, nature and amount of the catalyst and substrate. The catalytic behavior of the studied complexes was shown to be dependent on the conditions applied. In all reactions, acetophenone and 1- phenylethanol were the only observed products. Full article
(This article belongs to the Special Issue Hypervalent Iodine)
Open AccessArticle Asymmetric Synthesis of Double Bond Isomers of the Structure Proposed for Pyrinodemin A and Indication of Its Structural Revision
Molecules 2005, 10(1), 312-316; doi:10.3390/10010312
Received: 28 December 2004 / Revised: 24 January 2005 / Accepted: 24 January 2005 / Published: 31 January 2005
Cited by 21 | PDF Full-text (191 KB) | HTML Full-text | XML Full-text
Abstract
Asymmetric synthesis of double bond isomers ( )-2 (∆15’,16’) and ( )-3 (∆14’,15’) ofthe structure (1) (∆16’,17’) proposed for pyrinodemin A, a cytotoxic bis-pyridine alkaloidwith a unique cis-cyclopent[c]isoxazolidine moiety from [...] Read more.
Asymmetric synthesis of double bond isomers ( )-2 (∆15’,16’) and ( )-3 (∆14’,15’) ofthe structure (1) (∆16’,17’) proposed for pyrinodemin A, a cytotoxic bis-pyridine alkaloidwith a unique cis-cyclopent[c]isoxazolidine moiety from a marine sponge, has beenaccomplished. Pyrinodemin A was indicated to be a 1:1 racemic mixture of 2 fromcomparison of C18 and chiral HPLC analysis for pyrinodemin A and the syntheticcompounds as well as ESIMS data of oxidative degradation products of pyrinodemin A. Full article
(This article belongs to the Special Issue Hypervalent Iodine)

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