Photoinduced iodine-mediated tandem dehydrogenative Povarov cyclisation/C–H oxygenation reactions

Schendera, Eva; Villinger, Alexander; Brasholz, Malte

doi:10.1039/d0ob01494j

Cited by 3 publications

(1 citation statement)

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“…After reacting with 1.0 equiv of NIS, propargyl amidine 1 was converted into 5-iodomethyl imidazole 5 which would be nucleophilically attacked by an aromatic o -diamine 2 to deliver a complex A . Upon oxidation by the excess amount of NIS, A was converted into an imine B . , After intramolecular cyclization and sequential oxidation by air, the desired product 3 formed.…”

Section: Resultsmentioning

confidence: 99%

N-Iodosuccinimide-Mediated Synthesis of Benzo-Fused Bisimidazoles Enabled by a One-Pot Tandem Reaction of Fluorinated Propargyl Amidines

Feng

et al. 2023

J. Org. Chem.

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A N-iodosuccinimide (NIS)-mediated divergent and efficient tandem reaction between fluorinated propargyl amidines and aromatic o-diamines without any metal catalyst and additive under mild reaction conditions was developed for the synthesis of benzo-fused bisimidazoles in moderate to excellent yields. Preliminary mechanistic studies suggested that this reaction proceeded by an intermediate of secondary amine derived from 5iodomethyl imidazole, and NIS played another role of oxidation reagent to promote the formation of a benzimidazole motif.

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Section: Resultsmentioning

confidence: 99%

N-Iodosuccinimide-Mediated Synthesis of Benzo-Fused Bisimidazoles Enabled by a One-Pot Tandem Reaction of Fluorinated Propargyl Amidines

Feng

et al. 2023

J. Org. Chem.

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Spirooxindol‐1,3‐oxazine Alkaloids: Highly Potent and Selective Antitumor Agents Evolved from Iterative Structure Optimization

et al. 2022

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Spirooxindole‐1,3‐oxazines are a small and structurally unique class of spirooxindole alkaloids. To date, only four of these compounds have been isolated from natural sources, and their biological properties remained unknown thus far. Dioxyreserpine is a synthetic spirooxindole‐1,3‐oxazine, that can readily be prepared from the Rauvolfia alkaloid (–)‐reserpine by catalytic photooxygenation. While dioxyreserpine itself was now identified as a moderately effective antitumoral agent, structurally modified analogs of it emerged as a new class of highly potent and selective growth inhibitors of various human cancers, including pancreatic cancers. Systematic structural optimization ultimately led to an inhibitor displaying low‐micromolar IC50‐values against six cancer cell lines as well as selective apoptosis induction in vitro.

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Photocatalytic Azetidine Synthesis by Aerobic Dehydrogenative [2 + 2] Cycloadditions of Amines with Alkenes

2022

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Photocatalytic dehydrogenative [2 + 2] cycloadditions between amines and alkenes were developed that allow for the stereoselective and high-yielding synthesis of functionalized azetidines. The oxidative formal Aza Paternò–Büchi reactions are induced by photoredox-catalyzed aerobic oxidation of dihydroquinoxalinones 1 as the amines, and in the presence of structurally diverse alkenes 3 intermolecular [2 + 2] cyclization to dihydro-1H-azeto[1,2-a]quinoxalin-3(4H)-ones 4 occurs. The utility of the method is illustrated by the selective conversion of amino acid derived dihydroquinoxalinones 1, including oxidation-prone lysine and tryptophan derivatives.

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Photoinduced iodine-mediated tandem dehydrogenative Povarov cyclisation/C–H oxygenation reactions

Abstract: We report metal-free, photoinduced aerobic tandem dehydrogenative Povarov cyclisation / Csp3−H oxygenation reactions between N-aryl glycine esters and α-substituted styrenes, which efficiently lead to 4,4-disubstituted dihydroquinoline-3-ones under mild conditions. The...

Cited by 3 publications

References 30 publications

N-Iodosuccinimide-Mediated Synthesis of Benzo-Fused Bisimidazoles Enabled by a One-Pot Tandem Reaction of Fluorinated Propargyl Amidines

N-Iodosuccinimide-Mediated Synthesis of Benzo-Fused Bisimidazoles Enabled by a One-Pot Tandem Reaction of Fluorinated Propargyl Amidines

Spirooxindol‐1,3‐oxazine Alkaloids: Highly Potent and Selective Antitumor Agents Evolved from Iterative Structure Optimization

Photocatalytic Azetidine Synthesis by Aerobic Dehydrogenative [2 + 2] Cycloadditions of Amines with Alkenes

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Photoinduced iodine-mediated tandem dehydrogenative Povarov cyclisation/C–H oxygenation reactions

Abstract: We report metal-free, photoinduced aerobic tandem dehydrogenative Povarov cyclisation / Csp3−H oxygenation reactions between N-aryl glycine esters and α-substituted styrenes, which efficiently lead to 4,4-disubstituted dihydroquinoline-3-ones under mild conditions. The...

Cited by 3 publications

References 30 publications

N-Iodosuccinimide-Mediated Synthesis of Benzo-Fused Bisimidazoles Enabled by a One-Pot Tandem Reaction of Fluorinated Propargyl Amidines

N-Iodosuccinimide-Mediated Synthesis of Benzo-Fused Bisimidazoles Enabled by a One-Pot Tandem Reaction of Fluorinated Propargyl Amidines

Spirooxindol‐1,3‐oxazine Alkaloids: Highly Potent and Selective Antitumor Agents Evolved from Iterative Structure Optimization

Photocatalytic Azetidine Synthesis by Aerobic Dehydrogenative [2 + 2] Cycloadditions of Amines with Alkenes

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Photocatalytic Azetidine Synthesis by Aerobic Dehydrogenative [2 + 2] Cycloadditions of Amines with Alkenes