Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(21), С. 5428 - 5434
Опубликована: Янв. 1, 2023
Herein, the first example of umpolung α-regioselective 1,3-dipolar cycloaddition optically pure perhydroindole-2-carboxylic acid 1a with pyridinecarboxaldehydes 2 is described.
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
255
Chemistry - An Asian Journal, Год журнала: 2020, Номер 15(8), С. 1225 - 1233
Опубликована: Фев. 27, 2020
The spirooxindole unit is one of the most widely investigated compound skeletons existing in numerous natural and pharmaceutical molecules. Thus, a large number synthetic methodologies have already been reported to construct such core structure. trifluoromethyl group another privileged organic chemistry. introduction CF3 an framework can significantly improve properties molecule. In this context, efficient approach for construction trifluoromethyl-containing spirooxindoles becomes promising research direction among communities industry academia. Minireview, recent advances summarized discussed. addition, representative corresponding reaction mechanisms described as well.
Язык: Английский
Процитировано
79
Organic Letters, Год журнала: 2022, Номер 24(10), С. 2008 - 2013
Опубликована: Март 10, 2022
We report an unexpected dearomative periphery modification strategy for transforming quinolinium salts into structurally crowded pyrrolidine–tetrahydroquinoline polycyclic systems with complete regio- and diastereoselectivity. Importantly, the reaction pathway was regulated by simply tuning substituents, achieving substituent-directed divergent synthesis. The notable features of this transformation include readily available starting materials, green conditions, a simple workup procedure, high bond- ring-forming efficiency, diverse
Язык: Английский
Процитировано
29
Organic Letters, Год журнала: 2020, Номер 22(13), С. 5068 - 5073
Опубликована: Май 27, 2020
Reported herein is an unprecedented multicomponent one-pot dearomative multifunctionalization of commercially available azaarenes through in situ activation strategy, which not only achieved the first full exploitation reactive sites azaarenes, but also accomplished efficient synthesis bridged hydrogenated pyridines and (iso)quinolines a highly regioselective diastereoselective manner. In addition, we could successfully realize step-controlled trifunctionalization bifunctionalization quinolines.
Язык: Английский
Процитировано
42
Advanced Synthesis & Catalysis, Год журнала: 2020, Номер 363(6), С. 1702 - 1713
Опубликована: Дек. 31, 2020
Abstract An asymmetric (4+1) annulation of 3‐diazooxindoles/4‐diazooxisoquinolines with para ‐quinone methides, catalyzed by a chiral phosphoric acid, has been described. A wide range spiro[dihydrobenzofuran‐2,3′‐oxindoles/2,4′‐oxisoquinoline] derivatives were afforded excellent diastereo‐ and enantioselectivities. In this study, the possible reaction pathway was proposed synthetic applications shown tenfold scale‐up conversion as well further transformations into other structurally more complex spirocyclic compounds. The significance protocol is highlighted its metal‐free participation heterocyclic diazo compounds direct nucleophile extremely high efficiency in straightforward mild process to access structurally‐diverse spiro‐heterocyclic 2,3‐dihydrobenzofuran good stereocontrol. magnified image
Язык: Английский
Процитировано
41
Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(13), С. 3307 - 3312
Опубликована: Янв. 1, 2023
An unprecedented example of skeletal editing pyrrolidines to 1,2-oxazinanes expands the applicability scope “single-atom” skeletal-editing technologies.
Язык: Английский
Процитировано
15
Organic Letters, Год журнала: 2020, Номер 23(2), С. 358 - 364
Опубликована: Дек. 23, 2020
The switchable synthesis of 3-non, 3-mono, 3,3′-disubstituted 3,4-dihydroquinolin-2(1H)-ones was developed through a redox-neutral hydride-transfer/N-dealkylation/N-acylation strategy from o-aminobenzaldehyde with 4-hydroxycoumarin, and Meldrum's acid, respectively. unprecedented for the 3,3′-highly functionalized 3,4-dihydroquinolin-2(1H)-one has been realized in situ utilization released HCHO via o-QM involved Michael addition. In addition, synthetic utility this protocol well illustrated concise CYP11B2 inhibitor.
Язык: Английский
Процитировано
39
Organic Letters, Год журнала: 2020, Номер 22(3), С. 873 - 878
Опубликована: Янв. 9, 2020
New chalcone-based pyridinium salts have been successfully exploited, which could smoothly participate in the highly diastereoselective dearomatization with binucleophilic enaminones by taking advantage of their multiple reactive sites to construct bibridged benzoazepines up 89% yields. The key success was skillful and unprecedented C-3 functionalization new salts. This work not only provides a kind novel salt synthon but also achieves first complex challenging high synthetic efficiency.
Язык: Английский
Процитировано
37
Chemical Communications, Год журнала: 2020, Номер 57(3), С. 359 - 362
Опубликована: Дек. 8, 2020
An unexpected construction of functionalized π-extended indolizine polycycles through a one-pot two-step process comprising the base-promoted dearomative [3+2] cycloaddition and DDQ-mediated oxidative decarbonylation was developed.
Язык: Английский
Процитировано
35
Organic Letters, Год журнала: 2025, Номер unknown
Опубликована: Фев. 25, 2025
We report a visible-light photoredox-induced stereoselective radical 1,3-dipolar cycloaddition between tetrahydroisoquinolines and coumarin derivatives, providing platform for the efficient synthesis of pseudo-natural-inspired fused pentacyclic scaffolds. Using this protocol, diverse range valuable pyrrolo[2,1-a]isoquinolines were efficiently obtained in moderate to good yields excellent diastereoselectivities. Mechanistic investigations including control experiments light on/off studies indicated that reaction underwent induced process. The insights gained from our are expected advance general efforts toward green biology-oriented pseudo-natural products heterocyclic skeletons.
Язык: Английский
Процитировано
0