Hypervalent Iodine in Synthesis 91: A Mild and Efficient Method for the Halogenation of 6-Methyluracil Derivatives

2002 ◽  
Vol 2002 (12) ◽  
pp. 624-625 ◽  
Author(s):  
Dong Ping Cheng ◽  
Zhen Chu Chen ◽  
Qin Guo Zheng
Keyword(s):  
Efficient Method ◽  
Room Temperature ◽  
Hypervalent Iodine ◽  
Polymer Supported ◽  
High Yields

The combined reagent of iodobenzene diacetate (or polymer-supported iodobenzene diacetate) with iodine or bromine was used as an effective halogenative agent of 6-methyluracil derivatives to the corresponding 5-halo-6-methyluracil derivatives at room temperature with high yields.

UV-Light-Induced Dehydrogenative N-Acylation of Amines with 2-Nitrobenzaldehydes to Give 2-Aminobenzamides

Synthesis ◽  
2022 ◽  
Author(s):  
Dishu Zeng ◽  
Tianbao Yang ◽  
Niu Tang ◽  
Wei Deng ◽  
Jiannan Xiang ◽  
...  
Keyword(s):  
Amino Acid ◽  
Organic Synthesis ◽  
Efficient Method ◽  
Building Block ◽  
Room Temperature ◽  
Uv Light ◽  
Amino Acid Derivatives ◽  
One Pot ◽  
Plausible Mechanism ◽  
High Yields

A simple, mild, green and efficient method for the synthesis of 2-aminobenzamides was highly desired in organic synthesis. Herein, we developed an efficient, one-pot strategy for the synthesis of 2-aminobenzamides with high yields irradiated by UV light. 32 examples proceeded successfully by this photo-induced protocol. The yield reached up to 92%. The gram scale was also achieved easily. This building block could be applied in the preparation of quinazolinones derivatives. Amino acid derivatives could be employed smoothly at room temperature. Finally, a plausible mechanism was proposed.

An Efficient Ultrasound-assisted Method for the Synthesis of 1,4-Disubstituted Triazoles

2011 ◽  
Vol 66 (1) ◽  
pp. 77-82 ◽  
Author(s):  
Yuqin Jiang ◽  
Xiaolan Chen ◽  
Lingbo Qu ◽  
Junliang Wang ◽  
Jinwei Yuan ◽  
...  
Keyword(s):  
Efficient Method ◽  
Room Temperature ◽  
Ultrasound Irradiation ◽  
Ultrasound Assisted ◽  
High Yields ◽  
Optimized Conditions

An efficient method for the synthesis of 1,4-disubstituted triazoles has been developed with the help of ultrasound irradiation in water at room temperature. Under the optimized conditions, a novel series of 1,4-disubstituted 1,2,3-triazoles was synthesized in high yields

Polymer-Supported Formate and Magnesium: An Efficient Transfer Hydrogenation System for the Facile Reduction of Azo Compounds

2005 ◽  
Vol 2005 (2) ◽  
pp. 123-125 ◽  
Author(s):  
G. R. Srinivasa ◽  
K. Abiraj ◽  
D. Channe Gowda
Keyword(s):  
Efficient Method ◽  
Room Temperature ◽  
Low Cost ◽  
Selective Reduction ◽  
Hydrogen Donor ◽  
Transfer Hydrogenation ◽  
Azo Compounds ◽  
Magnesium Powder ◽  
Polymer Supported ◽  
Efficient Transfer

A mild and efficient method was developed for the chemo-selective reduction of azo compounds to the corresponding amine/s using recyclable polymer-supported formate as hydrogen donor in the presence of low cost magnesium powder at room temperature.

Benziodoxole-Derived Organosulfonates: The Strongest Hypervalent Iodine Electrophiles and Oxidants

Synlett ◽  
2019 ◽  
Vol 31 (04) ◽  
pp. 315-326 ◽  
Author(s):  
Viktor V. Zhdankin ◽  
Mekhman S. Yusubov ◽  
Pavel Postnikov ◽  
Akira Yoshimura
Keyword(s):  
Room Temperature ◽  
Trifluoromethanesulfonic Acid ◽  
High Reactivity ◽  
Hypervalent Iodine ◽  
Ionic Character ◽  
Primary Alcohols ◽  
Total Syntheses ◽  
X Ray ◽  
High Yields ◽  
Efficient Reagent

This account describes the development of organosulfonyloxy-substituted iodine(III) and iodine(V) benziodoxole derived reagents, which are thermally stable compounds with useful reactivity patterns. Iodine(III) benziodoxoles and pseudobenziodoxoles are powerful electrophiles and mild oxidants toward various unsaturated compounds. In particular, pseudocyclic benziodoxole-derived triflate (IBA-OTf) is an efficient reagent for oxidative heteroannulation reactions. Aldoximes react with nitriles in the presence of IBA-OTf at room temperature to give 1,2,4-oxadiazoles in high yields. Moreover, IBA-triflate is used as a catalyst in oxidative heteroannulations with m-chloroperoxybenzoic acid as the terminal oxidant. The iodine(V) benziodoxole derived tosylates, DMP-tosylate and IBX-tosylate, are superior oxidants for the oxidation of structurally diverse, synthetically useful alcohols, utilized as key precursors in the total syntheses of polyketide antibiotics and terpenes. And finally, the most powerful hypervalent iodine(V) oxidant, 2-iodoxybenzoic acid ditriflate (IBX·2HOTf), is prepared by treatment of IBX with trifluoromethanesulfonic acid. According to the X-ray data, the I–OTf bonds in IBX-ditriflate have ionic character, leading to the high reactivity of this reagent in various oxidations. In particular, IBX-ditriflate can oxidize polyfluorinated primary alcohols, which are generally extremely resistant to oxidation.1 Introduction2 Iodine(III) Benziodoxole Based Organosulfonates3 Pseudocyclic Iodine(III) Benziodoxole Triflate (IBA-triflate)4 Pseudocyclic Iodine(III) Benziodoxole Tosylates5 Iodine(V) Benziodoxole Derived Tosylates6 Iodine(V) Benziodoxole Derived Triflate (IBX-ditriflate)7 Conclusions

Electrophilic Substitution Reactions of Indoles with Carbonyl Compounds Using Ceric Ammonium Nitrate: A Novel and Efficient Method for the Synthesis of Di- and Tri-Indolylmethanes1

2003 ◽  
Vol 2003 (2) ◽  
pp. 72-74 ◽  
Author(s):  
C. Ramesh ◽  
N. Ravindranath ◽  
Biswanath Das
Keyword(s):  
Ammonium Nitrate ◽  
Efficient Method ◽  
Carbonyl Compounds ◽  
Electrophilic Substitution ◽  
Room Temperature ◽  
Ceric Ammonium Nitrate ◽  
Substitution Reactions ◽  
Electrophilic Substitution Reactions ◽  
High Yields

Ceric ammonium nitrate (CAN) is used to catalyse the electrophilic substitution reactions of indoles with carbonyl compounds at room temperature to produce di- and tri-indolylmethanes in high yields.

Novel One-pot Synthesis of Pyranocarbazole Derivatives via an Isocyanide-based Three-component Reaction

2020 ◽  
Vol 17 ◽  
Author(s):  
Visarapu Malathi ◽  
Pedavenkatagari Narayana Reddy ◽  
Pannala Padmaja
Keyword(s):  
Efficient Method ◽  
Atom Economy ◽  
Reaction Conditions ◽  
One Pot ◽  
Catalyst Free ◽  
One Pot Synthesis ◽  
Three Component Reaction ◽  
High Yields

Abstract:: An efficient method has been developed for the synthesis of new pyrano[3,2-c] and pyrano[3,2-a]carbazole de-rivatives via a three component reaction of 4-hydroxycarbazole or 2-hydroxycarbazole, isocyanides, and dialkylacetylenedi-carboxylates. Noteworthy features of this protocol include mild reaction conditions, catalyst-free, high atom-economy and high yields.

An Efficient Synthesis of 2-Substituted Quinazolin-4(3H)-ones by Using Recyclable Wang Resin Supported Sulfonic Acid Catalyst

2020 ◽  
Vol 17 ◽  
Author(s):  
Kalyani K. ◽  
Srinivasa Reddy Kallam
Keyword(s):  
Sulfonic Acid ◽  
Functional Group ◽  
Acid Catalyst ◽  
Sulphonic Acid ◽  
Isatoic Anhydride ◽  
Efficient Synthesis ◽  
Wang Resin ◽  
Polymer Supported ◽  
High Yields

Abstract:: An efficient synthesis of 2-substituted Quinazolin-4(3H)-ones has been developed from isatoic anhydride with various amidoximes by using recyclable polymer supported sulphonic acid catalyst. Excellent functional group compatibil-ity and high yields are the important features of this protocol.

One-pot Synthesis of Pyrazolone Sulfones by Iodine-catalyzed Sulfenylation of Pyrazolones with Aryl Sulfonyl Hydrazides Followed by Oxidation in Water

2018 ◽  
Vol 15 (3) ◽  
pp. 380-387
Author(s):  
Xia Zhao ◽  
Xiaoyu Lu ◽  
Lipeng Zhang ◽  
Tianjiao Li ◽  
Kui Lu
Keyword(s):  
Double Bond ◽  
Efficient Method ◽  
Room Temperature ◽  
Sulfonyl Chloride ◽  
Antibacterial Activities ◽  
Oxidation Reactions ◽  
Reaction Conditions ◽  
One Pot ◽  
X Ray ◽  
Amide Form

Aim and Objective: Pyrazolone sulfones have been reported to exhibit herbicidal and antibacterial activities. In spite of their good bioactivities, only a few methods have been developed to prepare pyrazolone sulfones. However, the substrate scope of these methods is limited. Moreover, the direct sulfonylation of pyrazolone by aryl sulfonyl chloride failed to give pyrazolone sulfones. Thus, developing a more efficient method to synthesize pyrazolone sulfones is very important. Materials and Method: Pyrazolone, aryl sulphonyl hydrazide, iodine, p-toluenesulphonic acid and water were mixed in a sealed tube, which was heated to 100°C for 12 hours. The mixture was cooled to 0°C and m-CPBA was added in batches. The mixture was allowed to stir for 30 min at room temperature. The crude product was purified by silica gel column chromatography to afford sulfuryl pyrazolone. Results: In all cases, the sulfenylation products were formed smoothly under the optimized reaction conditions, and were then oxidized to the corresponding sulfones in good yields by 3-chloroperoxybenzoic acid (m-CPBA) in water. Single crystal X-ray analysis of pyrazolone sulfone 4aa showed that the major tautomer of pyrazolone sulfones was the amide form instead of the enol form observed for pyrazolone thioethers. Moreover, the C=N double bond isomerized to form an α,β-unsaturated C=C double bond. Conclusion: An efficient method to synthesize pyrazolone thioethers by iodine-catalyzed sulfenylation of pyrazolones with aryl sulfonyl hydrazides in water was developed. Moreover, this method was employed to synthesize pyrazolone sulfones in one-pot by subsequent sulfenylation and oxidation reactions.

scholarly journals Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions

Molecules ◽  
2021 ◽  
Vol 26 (7) ◽  
pp. 1897
Author(s):  
Hideyasu China ◽  
Nami Kageyama ◽  
Hotaka Yatabe ◽  
Naoko Takenaga ◽  
Toshifumi Dohi
Keyword(s):  
Aqueous Solution ◽  
Room Temperature ◽  
Practical Method ◽  
Hypervalent Iodine ◽  
Mild Conditions ◽  
Sequential Procedures ◽  
Iodine Compounds ◽  
Practical Synthesis ◽  
Iodosobenzoic Acid ◽  
Lower Temperature

We report a convenient and practical method for the preparation of nonexplosive cyclic hypervalent iodine(III) oxidants as efficient organocatalysts and reagents for various reactions using Oxone® in aqueous solution under mild conditions at room temperature. The thus obtained 2-iodosobenzoic acids (IBAs) could be used as precursors of other cyclic organoiodine(III) derivatives by the solvolytic derivatization of the hydroxy group under mild conditions of 80 °C or lower temperature. These sequential procedures are highly reliable to selectively afford cyclic hypervalent iodine compounds in excellent yields without contamination by hazardous pentavalent iodine(III) compound.

Hypervalent Iodine in Synthesis. Part 90. A Mild and Efficient Method for the Iodination of Pyrazoles.

ChemInform ◽  
2003 ◽  
Vol 34 (46) ◽  
Author(s):  
Dong-Ping Cheng ◽  
Zhen-Chu Chen ◽  
Qin-Guo Zheng
Keyword(s):  
Efficient Method ◽  
Hypervalent Iodine
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