93435-57-5Relevant academic research and scientific papers
α-Xanthylmethyl Ketones from α-Diazo ketones
López-Mendoza, Pedro,Miranda, Luis D.
, p. 3777 - 3790 (2021/07/07)
A simple and efficient method to obtain α-xanthylmethyl ketones from α-diazo ketones is described. The reaction proceeds through a protonation/nucleophilic substitution sequence in the presence of p -toluenesulfonic acid and potassium ethyl xanthogenate as the nucleophile. As α-diazo ketones can be readily synthesized from ubiquitous carboxylic acids, a broad variety of xanthates can be obtained, including examples from naturally occurring substrates.
Evolution of N-Heterocycle-Substituted Iodoarenes (NHIAs) to Efficient Organocatalysts in Iodine(I/III)-Mediated Oxidative Transformations
Boelke, Andreas,Nachtsheim, Boris J.
supporting information, p. 184 - 191 (2019/12/11)
The reactivity of ortho-functionalized N-heterocycle-substituted iodoarenes (NHIAs) as organocatalysts in iodine(I/III)-mediated oxidations was systematically investigated in the α-tosyloxylation of ketones as the model reaction. During a systematic catalyst evolution, it was found that NH-triazoles and benzoxazoles have the most significant positive influence on the reactivity of the central iodine atom. A further catalyst improvement which focused on the substitution pattern of the arene revealed a remarkable ortho-effect. By introduction of an o-OMe group we were able to generate a novel NHIA with a so far unseen catalytic efficiency. This new catalyst is not only easy to synthesize but also enabled the α-tosyloxylation of carbonyl compounds at the lowest reported catalyst loading of only 1 mol%. Finally, the performance of this iodine(I) catalyst was successfully demonstrated in intramolecular oxidative couplings of biphenyls and oxidative rearrangements. (Figure presented.).
Regioselective three-component synthesis of 1,2-diarylindoles from cyclohexanones, α-hydroxyketones and anilines under transition-metal-free conditions
Li, Cheng,Xie, Yanjun,Xiao, Fuhong,Huang, Huawen,Deng, Guo-Jun
supporting information, p. 4079 - 4082 (2019/04/25)
A facile method for the one-pot synthesis of 1,2-diarylindoles under transition-metal-free conditions is described. Cyclohexanones were used as the aryl sources via the dehydrogenative aromatization process. One C-C and two C-N bonds were selectively formed via a domino reaction. This protocol provides a convenient approach for the construction of valuable bioactive 1,2-diarylindoles from readily available cyclohexanones, α-hydroxyketones and anilines.
Facile synthesis of polysubstituted cyclopropanes using α-tosyloxyketones
Rana, Neena,Nain, Sonia,Kumar, Dinesh,Kumar, Ravi
, p. 505 - 507 (2018/02/09)
A facile synthesis of polysubstituted cyclopropanes (5) by the treatment of pyridinium ylides, generated in situ from pyridinium toslyates (2), with arylidenemalonitrile (4) is presented. Pyridinium toslyates (2) were obtained by reacting α-tosyloxyketone
Synthesis of α-sulfonyloxyketones via iodobenzene diacetate (PIDA)-mediated oxysulfonyloxylation of alkynes with sulfonic acids
Zhang, Yang,Tan, Hua,Liu, Weibing
, p. 54017 - 54020 (2017/12/05)
A simple yet powerful method to synthesize a variety of α-sulfonyloxyketones has been developed. This novel method can be applied for the direct oxysulfonyloxylation of alkynes with sulfonic acids to access a variety of α-sulfonyloxyketones. Compared to the reported methods for the application of PIDA, this study expands its application scope and uses it not only as the oxidant but also as the carrier of O to form the carbonyl group in the products. In addition, under the established conditions, this methodology not only exhibits a broad substrate scope but also demonstrates exclusive regioselectivity with substrates of 1,2-disubstituted internal alkynes.
2,4,6-Tris(4-iodophenoxy)-1,3,5-triazine as a new recyclable "iodoarene" for in situ generation of hypervalent iodine(III) reagent for α-tosyloxylation of enolizable ketones
Thorat, Prerana B.,Bhong, Bhagyashree Y.,Shelke, Amol V.,Karade, Nandkishor N.
, p. 3332 - 3335 (2014/06/09)
The synthesis of 2,4,6-tris[(4-iodo)phenoxy)]-1,3,5-triazine 6, as a new recyclable nonpolymeric analogue of iodobenzene is achieved using the reaction of 2,4,6-trichloro-1,3,5-triazine with 4-iodophenol in the presence of KOH. The application of 6 as a r
Modified one-pot multicomponent diastereoselective synthesis of trans-2,3-Dihydrofuro[3,2-c]coumarins via in situ-generated α- tosyloxyketones
Kumar, Ravi,Wadhwa, Deepak,Hussain, Khalid,Prakash, Om
, p. 1802 - 1807 (2013/05/22)
A modified protocol for diastereoselective synthesis of differently substituted trans-2,3-dihydrofuro[3,2-c]coumarins is developed via, a one-pot multicomoponent reaction starting from aromatic aldehydes, 4-hydroxycoumarin, and α-tosyloxyacetophenones wit
An iodobenzene-catalysed domino route toward quinoxaline derivatives from simple ketones and o-phenylenediamines in one pot
Li, Xiaoqing,Zhou, Can,Hu, Zhiyan,Xu, Xiangsheng
, p. 579 - 581 (2013/10/22)
An iodobenzene-catalysed domino route to quinoxalines from ketones and o-phenylenediamines in one pot has been developed. This transformation consisted of the generation of Koser's generation, α-tosyloxylation of ketones, nucleophilic substitution and intramolecular dehydration with o-phenylenediamines, and dehydrogenation. Website
New concise and efficient synthesis of rubrolides C and e via intramolecular Wittig reaction
Tale, Nilesh P.,Shelke, Amol V.,Tiwari, Girdharilal B.,Thorat, Prerana B.,Karade, Nandkishor N.
experimental part, p. 852 - 857 (2012/06/16)
A short total synthesis of rubrolides C and E has been achieved in four steps, using readily available 4-methoxyacetophenone, 2-bromoacetic acid, and the appropriate aromatic aldehyde, in 46 and 45% yield, respectively. Key reactions involved are α-tosyloxylation of the aryl methyl ketone, intramolecular Wittig reaction, Knoevenagel condensation, and demethylation. Copyright
Iodobenzene-catalyzed synthesis of α-azidoketones and α-thiocyanatoketones from aryl ketones with MCPBA as a cooxidant
Chang, Ya-Li,Chung, Chi-Lin,Wu, Fang-Wen,Wang, Huey-Min,Hou, Rei-Sheu,Kang, Iou-Jiun,Chen, Ling-Ching
experimental part, p. 149 - 152 (2011/04/16)
Iodobenzene-catalyzed synthesis of α-azidoketones and α-thiocyanatoketones from aryl ketones with MCPBA as a cooxidant is described. The method is simple, rapid and practical, generating α-azidoketones and α-thiocyanatoketones from the aryl ketone without
