Visible-Light-Mediated Cascade 1,4-Hydrogen Atom Transfer versus Dearomative Spirocyclization of N-Benzylacrylamides: Divergent Access to Functionalized γ-Ketoamides and 2-Azaspiro[4.5]decanes

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 14, 2025

Visible-light-driven metal- and photocatalyst-free cascade 1,4-HAT dearomative spirocyclization of N-benzylacrylamides are described for sustainable synthesis a variety pharmaceutically important γ-ketoamides 2-Azaspiro[4.5]decanes in one pot good to excellent yields. Readily accessible nontoxic materials, expensive Ir or Ru mild conditions, functional group tolerance, operational simplicity, scalability enhance the practical value this protocol. Mechanistic studies reveal that acyl radicals generated from α-oxocarboxylic acids trigger rare spirocyclization. The synthetic potential environmentally benign method is further showcased by late-stage functionalization drug molecules, amino acid, peptides.

Язык: Английский

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Mn(OAc)3 promoted radical cyclization of vinyl isocyanides: Synthesis of isoquinoline-1-sulfonates and derivatives

Tetrahedron Letters, Год журнала: 2025, Номер unknown, С. 155629 - 155629

Опубликована: Май 1, 2025

Язык: Английский

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All-aqueous microfluidic printing of multifunctional bioactive microfibers promote whole-stage wound healing

Colloids and Surfaces B Biointerfaces, Год журнала: 2023, Номер 234, С. 113720 - 113720

Опубликована: Дек. 21, 2023

Язык: Английский

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Electrochemical selenylative ipso-Annulation of N-benzylacrylamides to seleno-azaspiro[4.5]decadienones

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(30), С. 6141 - 6148

Опубликована: Янв. 1, 2024

Construction of seleno azaspiro[4.5]decadienones using an electrochemical approach is achieved via domino selenylation/ ipso -annulation.

Язык: Английский

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Radical Cascade Annulation of Biphenyl Acrylamides to Dibenzoazepinones: Experimental and DFT Studies

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(31)

Опубликована: Июнь 6, 2024

Abstract An efficient method for the conversion of biphenyl acrylamides to dibenzoazepinones with −SCF 3 incorporation is described. This operationally simple radical cascade reaction employs CAN as an oxidant and exhibits good functional group tolerance. Substrates featuring −OCH , −CH −Br or −Cl at para ‐position aromatic ring a preference ipso ‐cyclization due intervention DMSO in reaction. Density theory (DFT) calculations provide valuable insights into reaction's energetics product selectivity.

Язык: Английский

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Manganese(iii) acetate in organic synthesis: a review of the past decade

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(23), С. 6850 - 6917

Опубликована: Янв. 1, 2024

In this review, we summarize the latest developments and applications of Mn(OAc) 3 in organic synthesis over past decade, focusing on efforts to achieve milder reaction conditions while expanding scope possibilities.

Язык: Английский

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Photoinduced Ag-Mediated Azaspirocyclic Approach Involves Cyclization and Dearomatization

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

Опубликована: Ноя. 12, 2024

A visible-light-promoted protocol for azaspirocyclic synthesis from

Язык: Английский

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