Journal of Organic Chemistry最新文献_第8页

Iodine-Promoted C–H Bond Amination Reaction for the Synthesis of Fused Tricyclic Heteroarenes

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2024-12-13 DOI: 10.1021/acs.joc.4c02282

Rachel E. Crittell, Rehema Nakiwala, Margaux J. Lavenue, Scott M. Hutchinson, Jeanne L. Bolliger

{"title":"Iodine-Promoted C–H Bond Amination Reaction for the Synthesis of Fused Tricyclic Heteroarenes","authors":"Rachel E. Crittell, Rehema Nakiwala, Margaux J. Lavenue, Scott M. Hutchinson, Jeanne L. Bolliger","doi":"10.1021/acs.joc.4c02282","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02282","url":null,"abstract":"Fused heterocyclic scaffolds, such as benzimidazoles or larger ring systems containing a benzimidazole fragment, are frequently encountered in pharmaceutical compounds and other biologically active molecules. While there are many examples of N9- and/or C3-substituted 9H-benzo[4,5]imidazo[2,1-c][1,2,4]triazoles, current examples of the regioselective preparation of N1-substituted 1H-benzo[4,5]imidazo[2,1-c][1,2,4]triazoles are limited to N1-aryl substituted compounds, which also contain a C3-substituent. Here, we report an iodine-promoted C–H bond amination reaction that allows the selective preparation of 1H-benzo[4,5]imidazo[2,1-c][1,2,4]triazoles with a variety of aryl and alkyl N1-substituents. Not only do these cyclization reactions allow access to a new substitution pattern on the benzo[4,5]imidazo[2,1-c][1,2,4]triazole scaffold, but they are also tolerant toward a wide range of functional groups, including esters, amides, alcohols, alkynes, and alkenes. Our findings expand the synthetic toolbox for the preparation of nitrogen containing fused heteroarenes.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"47 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142816357","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Palladium-Catalyzed Autotandem Ring-Opening of Cyclopropanols with Gem-Dibromoolefins for the Synthesis of β-Pyrrolo[1,2-a]quinolinyl Ketones

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2024-12-12 DOI: 10.1021/acs.joc.4c02061

Ping-Xin Zhou, Xue-Yan Du, Yang Liu, Si-Hui Qiu, Qiang Wang, Ying-Ying Kong, Yong-Min Liang

引用次数: 0

Controllable Synthesis of Benzo[b]furo[2,3-d]azepines or Furo[3,2-b]indoles via Intermolecular Oxidative Annulation of 2-(Furan-2-yl)anilines and Propargyl Carbonates versus Intramolecular C–H Amination Reactions

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2024-12-12 DOI: 10.1021/acs.joc.4c02293

Rong Ma, Yujie Qu, Pengcheng Guan, Minghui Liu, Yu Han, Feng Feng, Chengyu Wang

引用次数: 0

Nondirected Ortho C–H Arylation for One-Pot Synthesis of Biaryl Scaffolds via In Situ Generated Mixed Acetal

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2024-12-12 DOI: 10.1021/acs.joc.4c01984

Aparna Tyagi, Himanshu Gautam, Khyati Tripathi, Chinmoy K. Hazra

引用次数: 0

Synthesis and Application of 1-[18F]Fluoro-4-isothiocyanatobenzene for Radiofluorination of Peptides in Aqueous Medium

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2024-12-12 DOI: 10.1021/acs.joc.4c02370

Surendra Reddy Gundam, Mathew R. Callstrom, Mukesh K. Pandey

引用次数: 0

Palladium-Catalyzed Autotandem Ring-Opening of Cyclopropanols with Gem-Dibromoolefins for the Synthesis of β-Pyrrolo[1,2-a]quinolinyl Ketones

IF 3.3 2区化学

Journal of Organic Chemistry Pub Date : 2024-12-12 DOI: 10.1021/acs.joc.4c0206110.1021/acs.joc.4c02061

Ping-Xin Zhou*, Xue-Yan Du, Yang Liu, Si-Hui Qiu, Qiang Wang*, Ying-Ying Kong* and Yong-Min Liang,

引用次数: 0

Organocatalytic Hat Trick: 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD)-Catalyzed Synthesis of Cyclic Imides via an Amidation–Cyclization–Elimination Cascade

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2024-12-12 DOI: 10.1021/acs.joc.4c02649

Chunling Blue Lan, Karine Auclair

引用次数: 0

Silver Oxide Promoted Synthesis of Alpha O-GalNAc Containing Glyco-Amino Acids: Synthesis of Core 2 Containing Glyco-Amino Acids for Solid Phase Synthesis of Glycopeptides

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2024-12-12 DOI: 10.1021/acs.joc.4c01572

Ousman Boye, Lisa Nicholson, Anna Marstall, Brooke Van Engen, Marika Van Slageren, Noah Mulder, Mostafa Ali Eldeen, Abe Hall, Anjaneyulu Putta, Sandeep K. Misra, Joshua S. Sharp, Hailiang Joshua Zhu

{"title":"Silver Oxide Promoted Synthesis of Alpha O-GalNAc Containing Glyco-Amino Acids: Synthesis of Core 2 Containing Glyco-Amino Acids for Solid Phase Synthesis of Glycopeptides","authors":"Ousman Boye, Lisa Nicholson, Anna Marstall, Brooke Van Engen, Marika Van Slageren, Noah Mulder, Mostafa Ali Eldeen, Abe Hall, Anjaneyulu Putta, Sandeep K. Misra, Joshua S. Sharp, Hailiang Joshua Zhu","doi":"10.1021/acs.joc.4c01572","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01572","url":null,"abstract":"O-GalNAc glycans on glycoproteins with eight different core structures sharing a common α-glycosidic linkage (O-GalNAc-α-Ser/Thr) are critical in various physiological and pathological processes. Among the eight O-GalNAc glycan cores, core 2 characterized by a GlcNAcβ1–6(Galβ1–3)GalNAc structural motif plays a significant role in regulating diverse biological processes, such as immune response modulation, adhesive properties of selectins, and gastrointestinal tract protection. However, the large-quantity synthesis of core 2 containing glyco-amino acids for downstream solid-phase peptide synthesis is challenging. In this work, we successfully employed a silver oxide for coupling a 2-azido-galactosyl chloride donor with two acceptors, Fmoc-Ser/Thr-OtBu, respectively, for the large-scale synthesis of the two important intermediates, α-GalN3–Fmoc-Ser/Thr-OtBu, which can be further utilized for the large-scale synthesis of core 2 containing glyco-amino acids. The two intermediates, α-GalN3–Fmoc-Ser/Thr-OtBu, were utilized for synthesizing core 2 containing Fmoc-Ser/Thr-COOH. The synthesis of core 2 containing Fmoc-Ser-COOH was achieved on a 1.95 g scale, while the synthesis of core 2 containing Fmoc-Thr-COOH was achieved on a 0.38 g scale. Additionally, the synthesis of the 2-azido-galactosyl chloride donor was optimized into a three-step process with only one column chromatography purification. Finally, core 2 containing Fmoc-Ser/Thr-COOH were applied for the synthesis of glycosylated CCR1 and CCR5 N-terminal peptides.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"12 4 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142810031","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Synthesis, Protonation and Aromatic Characteristics of a Series of 1,10-Phenanthroline-Fused Porphyrinoids

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2024-12-12 DOI: 10.1021/acs.joc.4c01511

Victoria C. Ujah, Deyaa I. AbuSalim, Timothy D. Lash

{"title":"Synthesis, Protonation and Aromatic Characteristics of a Series of 1,10-Phenanthroline-Fused Porphyrinoids","authors":"Victoria C. Ujah, Deyaa I. AbuSalim, Timothy D. Lash","doi":"10.1021/acs.joc.4c01511","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01511","url":null,"abstract":"A series of porphyrin analogues with fused 1,10-phenanthroline units were synthesized. The proton NMR spectra for phenanthroline-fused heteroporphyrins showed significantly upfield shifted meso-proton resonances compared to related porphyrinoid systems and the peaks corresponding to alkyl substituents directly attached to these macrocycles were also observed further upfield. These results indicate that the presence of the phenanthroline unit leads to reduced diatropicity, but the internal NH resonance was also further upfield, a result that is inconsistent with this interpretation. A phenanthrene-fused carbaporphyrin gave an unexpectedly upfield singlet for the internal C–H at nearly −9 ppm, while the NH protons appeared at −6.8 ppm. These unusual chemical shifts again imply enhanced diatropicity but the reduced downfield shifts for the external protons indicates that the aromatic ring current has been significantly reduced. Similar results were obtained for phenanthroline-fused oxybenzi- and oxypyriporphyrins. Detailed analyses of the spectroscopic properties for these systems are reported and protonation studies were conducted. The conjugation pathways and aromatic properties were computationally analyzed using nucleus independent chemical shifts (NICS) and anisotropy of induced current density plots.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"4 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142810030","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Bifunctional Sodium Dithionite Promoted Radical-Polar Crossover Cyclization: Diversified Synthesis of Functionalized Cyclic Sultines

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2024-12-11 DOI: 10.1021/acs.joc.4c02606

Cheng-Jing Li, Meng-Yu Liu, Zhong-Lin Wei, Wei-Wei Liao

引用次数: 0