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Special Issue "Organic Iodine Chemistry"

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

Deadline for manuscript submissions: closed (31 December 2009)

Special Issue Editors

Guest Editor
Dr. Bimal K. Banik

Vice President, Research & Education Development, Community Health Systems of South Texas, 3135 S. Sugar Road Edinburg, Texas 78539, USA
E-Mail
Fax: +1 956 384 5006
Interests: organic synthesis, medicinal chemistry, beta lactams, polyaromatic compounds, catalysis, microwave-induced reactions, and synthetic methods
Guest Editor
Dr. Hideo Togo

Graduate School of Science, Chiba University, Japan
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Special Issue Information

Dear Colleagues,

In recent years, a large number of organic reactions have been investigated using molecule iodine-catalyzed and iodine-induced methods. Therefore, many new compounds have been synthesized using molecular iodine. Iodine is an inexpensive weak Lewis acid, non-toxic, and readily available reagent for various organic transformations and yields products with outstanding selectivity with minimum by products. In view of the increasingly expanding field of molecular iodine-mediated reactions and significant attention in this area from academic and industrial scientists, we believe a respectable journal should publish a whole issue on iodine mediated reactions toward the synthesis of important organic compounds under environmentally benign conditions. I am delighted that Molecules have come forward and ask me to take over this responsibility.

The main objective of this issue will be to provide useful information to researchers and students who are interested in the chemistry of iodine and its fascinating role in organic synthesis. Efforts will be made to include not only the synthesis of organic compounds but also to understand the mechanism of iodine-mediated reactions in different solvents including in water.

In summary, I have no doubt that this volume in Molecules will be extremely valuable resource for many groups who are working on organoiodine chemistry.

Prof. Dr. Bimal K. Banik

Hideo Togo, Ph. D.
Guest Editor

Keywords

  • iodine
  • catalysis
  • organic synthesis
  • selectivity
  • green chemistry and mechanism

Published Papers (12 papers)

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Research

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Open AccessArticle An Expeditious Iodine-Catalyzed Synthesis of 3-Pyrrole-substituted 2-Azetidinones
Molecules 2012, 17(10), 11570-11584; doi:10.3390/molecules171011570
Received: 10 September 2012 / Revised: 25 September 2012 / Accepted: 26 September 2012 / Published: 28 September 2012
Cited by 9 | PDF Full-text (314 KB) | HTML Full-text | XML Full-text
Abstract
2-Azetidinones and pyrroles are two highly important classes of molecules in organic and medicinal chemistry. A green and practical method for the synthesis of 3-pyrrole-substituted 2-azetidinones using catalytic amounts of molecular iodine under microwave irradiation has been developed. Following this method, a series
[...] Read more.
2-Azetidinones and pyrroles are two highly important classes of molecules in organic and medicinal chemistry. A green and practical method for the synthesis of 3-pyrrole-substituted 2-azetidinones using catalytic amounts of molecular iodine under microwave irradiation has been developed. Following this method, a series of 3-pyrrole- substituted 2-azetidinones have been synthesized with a variety of substituents at N-1 and at C-4. The procedure is equally effective for mono- as well as polyaromatic groups at the N-1 position of the 2-azetidinone ring. The C-4 substituent has no influence either on the yield or the rate of the reaction. Optically pure 3-pyrrole-substituted 2-azetidinones have also been synthesized following this methodology. No deprotection/rearrangement has been identified in this process, even with highly acid sensitive group-containing substrates. A plausible mechanistic pathway has also been suggested based on the evidence obtained from 1H-NMR spectroscopy. The extreme rapidity with excellent reaction yields is believed to be the result of a synergistic effect of the Lewis acid catalyst (molecular iodine) and microwave irradiation. Full article
(This article belongs to the Special Issue Organic Iodine Chemistry)
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Open AccessCommunication An Effective Microwave-Induced Iodine-Catalyzed Method for the Synthesis of Quinoxalines via Condensation of 1,2-Diamines with 1,2-Dicarbonyl Compounds
Molecules 2010, 15(6), 4207-4212; doi:10.3390/molecules15064207
Received: 28 March 2010 / Revised: 14 May 2010 / Accepted: 9 June 2010 / Published: 9 June 2010
Cited by 38 | PDF Full-text (383 KB)
Abstract A microwave-induced iodine-catalyzed simple, rapid and convenient synthesis of different types of quinoxalines via condensation of 1,2-diamines with 1,2-dicarbonyl compounds has been accomplished with an excellent yield. Full article
(This article belongs to the Special Issue Organic Iodine Chemistry)
Open AccessArticle Bohlmann-Rahtz Cyclodehydration of Aminodienones to Pyridines Using N-Iodosuccinimide
Molecules 2010, 15(5), 3211-3227; doi:10.3390/molecules15053211
Received: 22 March 2010 / Accepted: 20 April 2010 / Published: 30 April 2010
Cited by 7 | PDF Full-text (151 KB)
Abstract Cyclodehydration of Bohlmann-Rahtz aminodienone intermediates using N-iodosuccinimide as a Lewis acid proceeds at low temperature under very mild conditions to give the corresponding 2,3,6-trisubstituted pyridines in high yield and with total regiocontrol. Full article
(This article belongs to the Special Issue Organic Iodine Chemistry)
Open AccessArticle Conversion of Aryl Iodides into Aryliodine(III) Dichlorides by an Oxidative Halogenation Strategy Using 30% Aqueous Hydrogen Peroxide in Fluorinated Alcohol
Molecules 2010, 15(4), 2857-2871; doi:10.3390/molecules15042857
Received: 7 January 2010 / Revised: 24 February 2010 / Accepted: 19 March 2010 / Published: 20 April 2010
Cited by 13 | PDF Full-text (419 KB)
Abstract
Oxidative chlorination with HCl/H2O2 in 1,1,1-trifluoroethanol was used to transform aryl iodides into aryliodine(III) dihalides. In this instance 1,1,1-trifluoroethanol is not only the reaction medium, but is also an activator of hydrogen peroxide for the oxidation of hydrochloric acid to
[...] Read more.
Oxidative chlorination with HCl/H2O2 in 1,1,1-trifluoroethanol was used to transform aryl iodides into aryliodine(III) dihalides. In this instance 1,1,1-trifluoroethanol is not only the reaction medium, but is also an activator of hydrogen peroxide for the oxidation of hydrochloric acid to molecular chlorine. Aryliodine(III) dichlorides were formed in 72–91% isolated yields in the reaction of aryl iodides with 30% aqueous hydrogen peroxide and hydrochloric acid at ambient temperature. A study of the effect that substituents on the aromatic ring have on the formation and stability of aryliodine(III) dichlorides shows that the transformation is easier to achieve in the presence of the electron-donating groups (i.e. methoxy), but in this case the products rapidly decompose under the reported reaction conditions to form chlorinated arenes. The results suggest that oxidation of hydrogen chloride with hydrogen peroxide is the initial reaction step, while direct oxidation of aryl iodide with hydrogen peroxide is less likely to occur. Full article
(This article belongs to the Special Issue Organic Iodine Chemistry)
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Open AccessCommunication An Expeditious Synthesis of N-substituted Pyrroles via Microwave-Induced Iodine-Catalyzed Reactions under Solventless Conditions
Molecules 2010, 15(4), 2520-2525; doi:10.3390/molecules15042520
Received: 20 January 2010 / Revised: 1 March 2010 / Accepted: 2 April 2010 / Published: 9 April 2010
Cited by 27 | PDF Full-text (205 KB)
Abstract An expeditious synthesis of N-substituted pyrroles has been developed by reacting 2,5-dimethoxy tetrahydrofuran and several amines using a microwave-induced molecular iodine-catalyzed reaction under solventless conditions. Full article
(This article belongs to the Special Issue Organic Iodine Chemistry)
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Open AccessArticle I2-Catalyzed Oxidative Condensation of Aldoses with Diamines: Synthesis of Aldo-Naphthimidazoles for Carbohydrate Analysis
Molecules 2010, 15(3), 1340-1353; doi:10.3390/molecules15031340
Received: 2 February 2010 / Revised: 2 March 2010 / Accepted: 5 March 2010 / Published: 5 March 2010
Cited by 11 | PDF Full-text (281 KB)
Abstract
A novel method for the conversion of unprotected and unmodified aldoses to aldo-imidazoles has been developed. Using iodine as a catalyst in acetic acid solution, a series of mono- and oligosaccharides, including those containing carboxyl and acetamido groups, undergo an oxidative condensation reaction
[...] Read more.
A novel method for the conversion of unprotected and unmodified aldoses to aldo-imidazoles has been developed. Using iodine as a catalyst in acetic acid solution, a series of mono- and oligosaccharides, including those containing carboxyl and acetamido groups, undergo an oxidative condensation reaction with aromatic vicinal diamines at room temperature to give the corresponding aldo-imidazole products in high yields. No cleavage of the glycosidic bond occurs under the mild reaction conditions. The compositional analysis of saccharides is commonly realized by capillary electropheresis of the corresponding aldo-imidazole derivatives, which are easily synthesized by the reported iodine-promoted oxidative condensation. In addition, a series of aldo-imidazoles were determined by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI–TOF MS) to analyze molecular weight and ion intensity. The diamine-labeled saccharides showed enhanced signals in MALDI–TOF MS. The combined use of aldoimidazole derivatization and mass spectrometric analysis thus provides a rapid method for identification of saccharides, even when less than 1 pmol of saccharide is present in the sample. These results can be further applied to facilitate the isolation and analysis of novel saccharides. Full article
(This article belongs to the Special Issue Organic Iodine Chemistry)
Open AccessCommunication Remarkable Iodine-Catalyzed Synthesis of Novel Pyrrole- Bearing N-Polyaromatic β-Lactams
Molecules 2010, 15(2), 1082-1088; doi:10.3390/molecules15021082
Received: 22 December 2009 / Revised: 8 February 2010 / Accepted: 20 February 2010 / Published: 23 February 2010
Cited by 23 | PDF Full-text (165 KB)
Abstract
Because of their interesting biological properties various methods for the synthesis of substituted pyrroles are described in the literature. However, synthesis of pyrroles fused with a β-lactam ring has not been reported. Our group has demonstrated synthesis and biological evaluation of various β-lactams
[...] Read more.
Because of their interesting biological properties various methods for the synthesis of substituted pyrroles are described in the literature. However, synthesis of pyrroles fused with a β-lactam ring has not been reported. Our group has demonstrated synthesis and biological evaluation of various β-lactams as anticancer agents. The anticancer activities of these compounds have prompted us to study the synthesis of pyrroles bound to the β-lactams. We have identified an expeditious synthetic method for the preparation of pyrroles fused with β-lactams by reacting 3-amino β-lactams with acetonylacetone in the presence of catalytic amounts (5 mol%) of molecular iodine at room temperature. It has also been discovered that the reaction gives products under domestic and automated microwave oven irradiation. To our knowledge, there are no other prior reports that describe the synthesis of pyrrole-substituted β-lactams. Full article
(This article belongs to the Special Issue Organic Iodine Chemistry)
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Open AccessArticle New Lipophilic Piceatannol Derivatives Exhibiting Antioxidant Activity Prepared by Aromatic Hydroxylation with 2-Iodoxybenzoic Acid (IBX)
Molecules 2009, 14(11), 4669-4681; doi:10.3390/molecules14114669
Received: 2 October 2009 / Revised: 17 November 2009 / Accepted: 17 November 2009 / Published: 17 November 2009
Cited by 10 | PDF Full-text (384 KB)
Abstract
Piceatannol (E-3,5,3’,4’-tetrahydroxystilbene) is a phytoalexin synthesized in grapes in response to stress conditions. It exhibits strong antioxidant and antileukaemic activities due to the presence of the catechol moiety. To modify some physical properties like solubility, and miscibility in non-aqueous media some
[...] Read more.
Piceatannol (E-3,5,3’,4’-tetrahydroxystilbene) is a phytoalexin synthesized in grapes in response to stress conditions. It exhibits strong antioxidant and antileukaemic activities due to the presence of the catechol moiety. To modify some physical properties like solubility, and miscibility in non-aqueous media some new previously unreported piceatannol derivatives having lipophilic chains on the A-ring were prepared in good yields by a simple and efficient procedure. The key step was a chemo- and regioselective aromatic hydroxylation with 2-iodoxybenzoic acid (IBX). The new compounds showed antioxidant activity and seemed promising for possible applications as multifunctional emulsifiers in food, cosmetic and pharmaceutical fields. Full article
(This article belongs to the Special Issue Organic Iodine Chemistry)
Open AccessArticle Iodoarylation of Arylalkynes with Molecular Iodine in the Presence of Hypervalent Iodine Reagents
Molecules 2009, 14(9), 3132-3141; doi:10.3390/molecules14093132
Received: 6 August 2009 / Revised: 18 August 2009 / Accepted: 24 August 2009 / Published: 24 August 2009
PDF Full-text (76 KB)
Abstract
Iodoarylation of arylacetylenes was performed using a simple reagent system composed of molecular iodine and [bis(benzoyloxy)iodo]benzene. Most arylacetylenes efficiently underwent the iodoarylation reaction with electron-rich arenes to give trans 1,1-diaryl-2-iodoethene adducts regio- and stereoselectively. As an exception, the iodoarylation of p-methoxyphenylacetylene resulted
[...] Read more.
Iodoarylation of arylacetylenes was performed using a simple reagent system composed of molecular iodine and [bis(benzoyloxy)iodo]benzene. Most arylacetylenes efficiently underwent the iodoarylation reaction with electron-rich arenes to give trans 1,1-diaryl-2-iodoethene adducts regio- and stereoselectively. As an exception, the iodoarylation of p-methoxyphenylacetylene resulted in a mixture of E- and Z-isomers of the corresponding product. Full article
(This article belongs to the Special Issue Organic Iodine Chemistry)
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Review

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Open AccessReview Iodine-124: A Promising Positron Emitter for Organic PET Chemistry
Molecules 2010, 15(4), 2686-2718; doi:10.3390/molecules15042686
Received: 5 March 2010 / Revised: 7 April 2010 / Accepted: 9 April 2010 / Published: 13 April 2010
Cited by 43 | PDF Full-text (779 KB)
Abstract
The use of radiopharmaceuticals for molecular imaging of biochemical and physiological processes in vivo has evolved into an important diagnostic tool in modern nuclear medicine and medical research. Positron emission tomography (PET) is currently the most sophisticated molecular imaging methodology, mainly due to
[...] Read more.
The use of radiopharmaceuticals for molecular imaging of biochemical and physiological processes in vivo has evolved into an important diagnostic tool in modern nuclear medicine and medical research. Positron emission tomography (PET) is currently the most sophisticated molecular imaging methodology, mainly due to the unrivalled high sensitivity which allows for the studying of biochemistry in vivo on the molecular level. The most frequently used radionuclides for PET have relatively short half-lives (e.g. 11C: 20.4 min; 18F: 109.8 min) which may limit both the synthesis procedures and the time frame of PET studies. Iodine-124 (124I, t1/2 = 4.2 d) is an alternative long-lived PET radionuclide attracting increasing interest for long term clinical and small animal PET studies. The present review gives a survey on the use of 124I as promising PET radionuclide for molecular imaging. The first part describes the production of 124I. The second part covers basic radiochemistry with 124I focused on the synthesis of 124I-labeled compounds for molecular imaging purposes. The review concludes with a summary and an outlook on the future prospective of using the long-lived positron emitter 124I in the field of organic PET chemistry and molecular imaging. Full article
(This article belongs to the Special Issue Organic Iodine Chemistry)
Open AccessReview Molecular Iodine—An Expedient Reagent for Oxidative Aromatization Reactions of α,β-Unsaturated Cyclic Compounds
Molecules 2009, 14(12), 5308-5322; doi:10.3390/molecules14125308
Received: 26 November 2009 / Revised: 9 December 2009 / Accepted: 15 December 2009 / Published: 16 December 2009
Cited by 28 | PDF Full-text (358 KB)
Abstract Prompted by the scant attention paid by published literature reviews to the applications of molecular iodine in oxidative aromatization reactions, we decided to review methods developed to-date involving iodine as an oxidant to promote aromatization of α,β-unsaturated cyclic compounds. Full article
(This article belongs to the Special Issue Organic Iodine Chemistry)
Open AccessReview Molecular Iodine-Mediated Cyclization of Tethered Heteroatom-Containing Alkenyl or Alkynyl Systems
Molecules 2009, 14(12), 4814-4837; doi:10.3390/molecules14124814
Received: 10 October 2009 / Revised: 9 November 2009 / Accepted: 12 November 2009 / Published: 25 November 2009
Cited by 82 | PDF Full-text (352 KB)
Abstract
Molecular iodine has established itself as a readily available and easy-to-handle electrophilic and oxidizing reagent used in various organic transformations. In this review attention is focused on the use of molecular iodine in promoting cyclization (iodocyclization and cyclodehydroiodination) of tethered heteroatom-containing alkenyl or
[...] Read more.
Molecular iodine has established itself as a readily available and easy-to-handle electrophilic and oxidizing reagent used in various organic transformations. In this review attention is focused on the use of molecular iodine in promoting cyclization (iodocyclization and cyclodehydroiodination) of tethered heteroatom-containing alkenyl or alkynyl systems. Full article
(This article belongs to the Special Issue Organic Iodine Chemistry)
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