Assembly of Thiazino[3,4‐a]isoquinoline and Thiazepino[5,4‐a]isoquinoline Frameworks from Isoquinolinium 1,4‐Zwitterionic Thiolates via [5 + 1] and [5 + 2] Cycloaddition Reactions DOI
Jiyun Wang, Yuting Wang,

Zou Xiao

и другие.

European Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Окт. 18, 2024

Abstract Two cycloaddition modes of isoquinolinium 1,4‐zwitterionic thiolates have been established. Upon choosing α ‐bromo ketones as the counterpart, a range isoquinoline‐fused thiazines can be attained with yields ranging from moderate to excellent through formal [5+1] reaction pathway, exhibiting remarkable substrate adaptability and resilience diverse functional groups. Additionally, library unprecedented thiazepino[5,4‐ ]isoquinolines, novel category seven‐membered heterocycles, has synthesized via [5+2] pathway utilizing acetylenedicarboxylate reactive component. Notably, this process stands out for its exceptional 100 % atomic utilization efficiency.

Язык: Английский

Chameleonic Reactivity of Imidoyl Sulfoxonium Ylides: Access to Functionalized Pyrroles and Dihydro-pyridines DOI
Jingnan Xu,

Ren‐Yin Yang,

Bo Xu

и другие.

Organic Letters, Год журнала: 2024, Номер 26(1), С. 62 - 67

Опубликована: Янв. 3, 2024

We have found a chameleonic reactivity of imidoyl sulfoxonium ylides. On the one hand, ylides react with electron-deficient reagents, such as alkynyl esters, to lead formation 1,2-dihydro-pyridines. The methyl group attached sulfur atom acts methylene donor. other pyridinium 1,4-zwitterionic thiolates, which leads functionalized pyrroles. Both transformations feature mild reaction conditions and good functional tolerance.

Язык: Английский

Процитировано

9

Formation of Trideuteromethylated Artifacts of Pyrrole-Containing Natural Products DOI
Maria Orfanoudaki,

Rhone K. Akee,

Lucero Martínez-Fructuoso

и другие.

Journal of Natural Products, Год журнала: 2024, Номер 87(2), С. 415 - 423

Опубликована: Янв. 31, 2024

Pyrrole-containing natural products form a large group of structurally diverse compounds that occur in both terrestrial and marine organisms. In the present study formation trideuteromethylated artifacts pyrrole-containing was investigated, focusing on discorhabdins. Three deuterated discorhabdins, 1, 3, 5, were identified to be isolation procedure caused by presence DMSO-d6 during NMR sample preparation handling. additional semisynthetic derivatives, 7–9, made investigation mechanism formation, which shown driven trideuteromethyl radicals water, methanol, TFA, traces iron solvent. Generation also confirmed for other classes metabolites, namely, makaluvamines, tambjamines, dibromotryptamines, had been dissolved structure elucidation process. Semisynthetic discorhabdins assessed antiproliferative activity against panel human tumor cell lines, 14-trideuteromethyldiscorhabdin L (3) averaged low micromolar potency.

Язык: Английский

Процитировано

3

Copper(I) Iodide Catalyzed [3 + 3] Annulation of Iodonium Ylides with Pyridinium 1,4-Zwitterionic Thiolates for the Synthesis of 1,4-Oxathiin Scaffolds DOI Creative Commons
Àlex Díaz‐Jiménez, Stuart C. D. Kennington, Anna Roglans

и другие.

Organic Letters, Год журнала: 2023, Номер 25(26), С. 4830 - 4834

Опубликована: Июнь 26, 2023

The selective assembly of the 1,4-oxathiin nucleus has been treated as a powerful strategy to access this scaffold present in molecules with very interesting properties. In study, chameleon-like reactivity pyridinium 1,4-zwitterionic thiolates is exploited assemble core through [3 + 3] annulation. optimal annulation partner found be iodonium ylide cyclic 1,3-diketones. developed protocol allows synthesis variety bicyclic derivatives under mild conditions copper(I) iodide catalysis. Access benzoannulated 1,4-oxathiins achieved iodine-mediated aromatization initially obtained compounds.

Язык: Английский

Процитировано

7

Diastereoselective dearomative bifunctionalization of isoquinolinium salts to access bridged tetrahydroisoquinolines DOI

Jiaqi Pei,

Tiantian Tang,

Jianing Zhang

и другие.

New Journal of Chemistry, Год журнала: 2024, Номер 48(37), С. 16151 - 16154

Опубликована: Янв. 1, 2024

We report a diastereoselective dearomative bifunctionalization strategy of using isoquinolinium salts to access bridged tetrahydroisoquinolines through one-pot three-component cascade process.

Язык: Английский

Процитировано

0

[(5 + 1) ‐ 1] Cyclization of Nitroepoxides to Pyridinium 1,4‐Zwitterionic Thiolates for the Synthesis of Indolizine Derivatives DOI

Alhajaj Almaani,

Ahmad Takallou, Yazdanbakhsh Lotfi Nosood

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер unknown

Опубликована: Окт. 18, 2024

Abstract The synthesis of indolizine derivatives was achieved through the reaction pyridinium 1,4‐zwitterionic thiolates with a diverse array 2‐methyl‐2‐nitro‐3‐aryloxiranes. Subsequent investigations unveiled synthetic route to indolizines via stepwise [(5+1)−1] pathway, unstable pyridothiazines serving as transient intermediates. DFT calculations elucidated that this transformation entails sequential annulation, deacylation, desulfurization, and oxidation steps.

Язык: Английский

Процитировано

0

Assembly of Thiazino[3,4‐a]isoquinoline and Thiazepino[5,4‐a]isoquinoline Frameworks from Isoquinolinium 1,4‐Zwitterionic Thiolates via [5 + 1] and [5 + 2] Cycloaddition Reactions DOI
Jiyun Wang, Yuting Wang,

Zou Xiao

и другие.

European Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Окт. 18, 2024

Abstract Two cycloaddition modes of isoquinolinium 1,4‐zwitterionic thiolates have been established. Upon choosing α ‐bromo ketones as the counterpart, a range isoquinoline‐fused thiazines can be attained with yields ranging from moderate to excellent through formal [5+1] reaction pathway, exhibiting remarkable substrate adaptability and resilience diverse functional groups. Additionally, library unprecedented thiazepino[5,4‐ ]isoquinolines, novel category seven‐membered heterocycles, has synthesized via [5+2] pathway utilizing acetylenedicarboxylate reactive component. Notably, this process stands out for its exceptional 100 % atomic utilization efficiency.

Язык: Английский

Процитировано

0