Organic Chemistry Frontiers, Год журнала: 2023, Номер 11(3), С. 809 - 815
Опубликована: Дек. 11, 2023
A new type of nucleophile-intercepted Meyer–Schuster rearrangement mediated by pyridine N -oxide under metal-free conditions using a catalytic amount acid is disclosed. It enables synthesis 2-acyl benzofurans and indoles in 56–>99% yields.
Язык: Английский
Nature Chemistry, Год журнала: 2022, Номер 15(1), С. 43 - 52
Опубликована: Дек. 5, 2022
Язык: Английский
Процитировано
146
Journal of the American Chemical Society, Год журнала: 2025, Номер unknown
Опубликована: Янв. 8, 2025
The asymmetric and divergent total syntheses of two phragmalin (moluccensins G H) khayanolide-type (krishnolide F khayseneganin F) limonoids were disclosed, which employed a torquoselective interrupted Nazarov cyclization as the key step. Taken together with Liebeskind-Srogl coupling, benzoin condensation, bidirectional acyloin rearrangements, our strategy would simplify synthetic design both facilitate their modular syntheses. Moreover, described approach also provides additional insights into biosynthetic relationships between these distinct skeletons.
Язык: Английский
Процитировано
2
Nature Reviews Chemistry, Год журнала: 2024, Номер 8(5), С. 304 - 318
Опубликована: Апрель 4, 2024
Язык: Английский
Процитировано
10
Molecules, Год журнала: 2023, Номер 28(2), С. 686 - 686
Опубликована: Янв. 10, 2023
The Nef reaction (nitro to carbonyl group conversion) and related Meyer are among the key transformations of aliphatic nitro compounds. interrupted versions these reactions in which normal pathway is redirected a different end product by an external nucleophile much less common, albeit processes substantially increase synthetic potential In this review, examples summarized, prospects methodology diversity-oriented organic synthesis analyzed. bibliography contains 90 references.
Язык: Английский
Процитировано
17
Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(29)
Опубликована: Март 31, 2023
Abstract Benzothiophenes, activated by oxidation to the corresponding S ‐oxides, undergo C−H/C−H‐type coupling with phenols give C4 arylation products. While an electron‐withdrawing group at C3 of benzothiophene is important, process operates without a directing and metal catalyst, thus rendering it compatible sensitive functionalities—e.g. halides formyl groups. Quantum chemical calculations suggest formal stepwise mechanism involving heterolytic cleavage aryloxysulfur species π‐complex phenoxonium cation. Subsequent addition cation position favored over C3; Fukui functions predict that major regioisomer formed more electron‐rich between C4. Varied selective manipulation products showcase synthetic utility metal‐free process.
Язык: Английский
Процитировано
14
Organic Letters, Год журнала: 2025, Номер unknown
Опубликована: Фев. 17, 2025
Interrupted reactions redirect established processes, often resulting in unexpected and novel outcomes. By employing a building block containing both acidic oxo functionalities tethered to the same carbon, we uncovered interrupted variants of Ugi Passerini reactions. More than 20 derivatives with peptide-like framework have been synthesized, demonstrating broad scope versatility these Additional studies explored use various nucleophiles postmodifications expand even more chemical diversity.
Язык: Английский
Процитировано
0
ACS Central Science, Год журнала: 2025, Номер unknown
Опубликована: Апрель 10, 2025
A multidisciplinary platform is presented to address aryl hydrocarbon receptor (AhR) modulation. rewired Yonemitsu multicomponent reaction with indole 2-carboxaldehydes and nucleophilic species was designed access a family of 6-substituted indolocarbazoles. The conformational behavior these compounds examined rationalize their axial chirality. In silico docking molecular simulations highlighted key features implicated in binding AhR. Furthermore, the synthesis linkable derivatives allowed direct development conjugated entities. Reporter gene target expression analyses identified novel structures as potent noncytotoxic activating AhR ligands, that can be extended bifunctional molecules. anti-inflammatory properties agonists were assessed interleukin-13 treated keratinocytes. Altogether, synergistic research synthetic computational chemistry integrated biological studies opens avenues toward understanding roles targeted therapeutics.
Язык: Английский
Процитировано
0
Sustainable materials and technologies, Год журнала: 2022, Номер 32, С. e00394 - e00394
Опубликована: Янв. 24, 2022
Язык: Английский
Процитировано
16
Chemistry - A European Journal, Год журнала: 2024, Номер 30(20)
Опубликована: Фев. 26, 2024
Abstract The particular and unique mechanism of the copper‐catalyzed reaction between azides alkynes (CuAAC) has not only allowed for efficient synthesis 1,2,3‐trisubstituted 1,4‐triazoles in excellent yields under mild conditions, becoming quintessential click reaction, but it also enabled straightforward formation a metallocycle intermediate, copper triazolyl. This, suitable conditions able to suppress its protonolysis, can be used either creation new bicyclic triazolyl structures or generation novel three four‐component reactions. aim this review is rationalize unify all these transformations, which are collectively referred as “interrupted reactions”.
Язык: Английский
Процитировано
3
Organic Letters, Год журнала: 2024, Номер 26(15), С. 3279 - 3283
Опубликована: Апрель 5, 2024
Chiral spiro-polycyclic oxindoles are valuable heterocyclic ring systems that widely distributed in natural alkaloids and biologically active compounds. Herein, we reported an asymmetric tandem Michael addition/interrupted Nef reaction of nitromethane with oxindole-derived alkenes catalyzed by a chiral 2-aminobenzimidazole bifunctional organocatalyst. A series novel enantiomerically enriched oxindole derivatives bearing oxime group were synthesized moderate to excellent isolated yields (up 99%) level enantioselectivities 99% ee). Furthermore, the antiproliferation activity resulting evaluated, compound 2d demonstrated promising anticancer properties against HCT116 (IC50 = 14.08 μM) HT29 15.46 cell lines.
Язык: Английский
Процитировано
3