Controllable Synthesis of N- and O-Containing Heterocycles via Formal [3 + 2] and [5 + 2] Cyclizations

Organic Letters, Год журнала: 2023, Номер 26(1), С. 6 - 11

Опубликована: Дек. 29, 2023

The controllable synthesis of spirooxindole–dihydrofurans and spirooxindole–benzazepines was developed through formal [3 + 2] [5 cyclization reactions from 2-(2-oxoindolin-3-yl)malononitriles ortho-aminobenzaldehydes, respectively. A variety spirooxindole-benzazepines were facilely constructed via a furan ring-open-involved hydride transfer/cyclization process. It is noteworthy that the application hydride-transfer-involved strategy for construction spirobenzazepines unprecedented. In addition, spiro N- O-containing heterocycles highly functionalized by amino, amide, cyano groups, which conducive to late-stage functionalization.

Язык: Английский

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Diversity-oriented synthesis of indole-fused scaffolds and bis(indolyl)methane from tosyl-protected tryptamine

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(14), С. 2824 - 2834

Опубликована: Янв. 1, 2024

Diversity-oriented synthesis of indole-1,2-fused 1,4-benzodiazepines, tetrahydro-β-carbolines, and 2,2′-bis(indolyl)methanes is presented by control reaction sites.

Язык: Английский

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Intermolecular Interception of α-Oxo Gold Carbenes of Nitroalkyne Cycloisomerization with 1,2-Benzo[d]isoxazole: Synthesis of Functionalized Quinazoline 1-Oxides

The Journal of Organic Chemistry, Год журнала: 2021, Номер 86(15), С. 10874 - 10882

Опубликована: Июль 27, 2021

The known nitrogen-transfer reagent 1,2-benzo[d]isoxazole has been used to trap the postulated α-oxo gold carbene intermediate involved in [Au]-catalyzed internal redox process of 2-alkynylnitrobenzenes. This led us develop a general convergent method for synthesis highly functionalized quinazoline 1-oxides.

Язык: Английский

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Synthesis of Dihydroquinolinone Derivatives via the Cascade Reaction of o-Silylaryl Triflates with Pyrazolidinones

The Journal of Organic Chemistry, Год журнала: 2021, Номер 86(21), С. 15203 - 15216

Опубликована: Окт. 1, 2021

Presented herein is a novel synthesis of dihydroquinolinone derivatives through an unprecedented cascade reaction o-silylaryl triflates with pyrazolidinones. Mechanistically, the formation title products believed to involve procedure including in situ aryne and its addition pyrazolidinone followed by N–N bond cleavage intramolecular C–C formation/annulation. Compared literature methods for dihydroquinolinones, this protocol has advantages such as multistep transformations accomplished one pot, broad substrate scope, mild conditions, good tolerance diverse functional groups. In addition, thus obtained demonstrated significant vitro antiproliferative activity selected human cancer cell lines.

Язык: Английский

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Switchable construction of oxa-heterocycles with diverse ring sizes via chemoselective cyclization controlled by dibrominated compounds

Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(22), С. 6187 - 6193

Опубликована: Янв. 1, 2022

Switchable construction of oxa-heterocycles with diverse ring sizes has been developed by performing dibrominated-compound-controlled chemoselective cyclization and subsequent derivatization.

Язык: Английский

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