Asian Journal of Organic Chemistry, Год журнала: 2019, Номер 8(8), С. 1385 - 1389
Опубликована: Май 6, 2019
Abstract A Rh‐catalyzed [5+1] cycloaddition reaction for the synthesis of spirocyclicindoline imine from 3‐diazoindolin‐2‐imine with benzo[ d ]isoxazole is reported. The proceeds under gentle catalytic conditions, thus giving expected spiro[benzo[ e ][1,3]oxazine‐2,3′‐indolin]‐2‐imines good functional‐group tolerance.
Язык: Английский
Organic Chemistry Frontiers, Год журнала: 2021, Номер 8(5), С. 1026 - 1084
Опубликована: Янв. 1, 2021
This review summaries recent synthetic developments towards spirocyclic oxindoles and applications as valuable medicinal targets.
Язык: Английский
Процитировано
253
Chemical Communications, Год журнала: 2017, Номер 53(81), С. 11201 - 11204
Опубликована: Янв. 1, 2017
A TfOH-catalyzed highly diastereoselective Michael addition/ketalization sequence of 3-hydroxyoxindoles and ortho-hydroxychalcones was developed, leading to biologically important bridged ketal spirooxindoles in moderate excellent yields. Moreover, some chemical transformations were carried out further extend the structural complexity diversity.
Язык: Английский
Процитировано
71
Synthesis, Год журнала: 2022, Номер 54(13), С. 2927 - 2975
Опубликована: Фев. 14, 2022
Abstract This review summarizes the latest developments in asymmetric domino reactions, with emphasis on preparation of spiro compounds. Discussions stereoselectivity transformations, reaction mechanisms, rationalization stereochemical outcome, and applications reactions to synthesis biologically active molecules natural products are included when appropriate. 1 Introduction 2 Asymmetric Domino Reactions 2.1 Initiated by Michael 2.2 Mannich 2.3 Knoevenagel 2.4 Cycloaddition 2.5 Metal Insertion 2.6 Other Mechanisms 3 Conclusion
Язык: Английский
Процитировано
29
The Journal of Organic Chemistry, Год журнала: 2018, Номер 83(7), С. 3679 - 3687
Опубликована: Март 13, 2018
The first highly diastereoselective Michael addition/condensation/Friedel–Crafts alkylation cascade reaction of 3-indolyl-substituted oxindoles with ortho-hydroxychalcones was established, which afforded a wide range polycyclic indole-bridged chroman spirooxindoles novel and complex scaffolds in moderate to excellent yields.
Язык: Английский
Процитировано
58
Advanced Synthesis & Catalysis, Год журнала: 2017, Номер 359(21), С. 3782 - 3791
Опубликована: Сен. 15, 2017
Abstract Constructing chiral bispirooxindoles is difficult to achieve but highly attractive owing their many potential applications in medicinal chemistry. Here we present an asymmetric [3+2] annulation reaction of Morita–Baylis–Hillman carbonates from isatins and isatin‐based N ‐Boc‐ketimines under the catalysis a newly designed multifunctional 4‐dimethylaminopyridine‐type substance. The shows high γ‐regioselectivity, producing complex 1,2‐bispirooxindoles incorporating dihydropyrrolidine motif excellent yields with moderate outstanding stereoselectivity ( dr >19:1, up >99% ee ). This protocol has been expanded utilize trifluoromethyl‐containing ketimines, delivering complicated architectures fused spirocyclic frameworks modest enantioselectivity. magnified image
Язык: Английский
Процитировано
54
Advanced Synthesis & Catalysis, Год журнала: 2016, Номер 358(23), С. 3777 - 3785
Опубликована: Ноя. 4, 2016
Abstract The introduction of a trifluoromethyl group into the 2′‐position spiro‐pyrrolidine‐3,3′‐oxindoles is described. By using 1 mol% quinine‐derived squaramide as catalyst, 2,2,2‐trfluoroethylamine (CF 3 CH 2 NH )‐derived ketimine transformed initially trifluoromethylimine through an umpolung reaction. subsequent 1,3‐dipolar cycloaddition gives pharmaceutical important target compounds in excellent yields, enantioselectivities and diastereoselectivies. magnified image
Язык: Английский
Процитировано
51
The Journal of Organic Chemistry, Год журнала: 2017, Номер 82(11), С. 5669 - 5677
Опубликована: Май 5, 2017
An efficient Cu(OTf)2-catalyzed Friedel–Crafts alkylation/cyclizaiton sequence of 3-substituted indoles with isatin-derived oxodienes was developed, and a series structurally complex diverse pyrrolo[1,2-a]indole spirooxindoles were first obtained in up to 99% yields. This protocol proved be quite general also robust for the synthesis 9H-pyrrolo[1,2-a]indoles.
Язык: Английский
Процитировано
47
Organic & Biomolecular Chemistry, Год журнала: 2016, Номер 15(4), С. 984 - 990
Опубликована: Дек. 24, 2016
The first DBU-catalyzed Michael/Pinner/isomerization cascade reaction of 3-hydrooxindoles with isatylidene malononitriles was developed, and the corresponding highly functionalized bispirooxindoles containing a fully substituted dihydrofuran motif were obtained in up to 92% yields. This protocol also provides an efficient method for synthesis α-cyano-γ-butyrolactone bispirooxindole. In addition, one-pot three-component conducted. Also, asymmetric version achieved.
Язык: Английский
Процитировано
41
Organic & Biomolecular Chemistry, Год журнала: 2020, Номер 18(42), С. 8572 - 8596
Опубликована: Янв. 1, 2020
Spiro-epoxy/aziridine oxindole frameworks are considered as an efficient structural toolbox to obtain C3-functionalised derivatives. These 3,3'-spiro-cyclic precursors highly susceptible towards nucleophiles owing their inherent ring strain. Their versatile reactivity has opened many potential synthetic transformations, allowing access bioactive molecules well natural products. The present review aims elaborate various enabling strategies applied in the successful synthesis of strained spiro-cyclic scaffolds. Furthermore, nucleophilic ring-opening/expansion and cycloaddition reactions spiro-epoxy/aziridine discussed. Moreover, mechanistic insights define regio- stereo-chemical outcome products have also been highlighted briefly.
Язык: Английский
Процитировано
36
Tetrahedron, Год журнала: 2025, Номер unknown, С. 134468 - 134468
Опубликована: Янв. 1, 2025
Язык: Английский
Процитировано
0