Synthesis of sulfur-containing benzo[<i>b</i>]pyrrolo[2,1-<i>c</i>][1,4]oxazine-3,9-diones: blue light promoted radical cyclization process

Pan, Feng; Hao-Hu, Li; Wang, Xiaohua; Luo, Liwen; Lin, Yanfei; Yu, Qing; Xie, Wei; Zhang, Lianpeng

doi:10.1039/d3ra02247a

Cited by 3 publications

(1 citation statement)

References 61 publications

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“…In this regard, Lin and co-workers built up a method to synthesize thio(seleno)-containing spirotricycles 114, starting from N-arylpropiolamides 112 and thio(seleno)phenols 97/113, employing blue light, HCl, in MeCN at 60 °C in air (Scheme 42). [88] In the scope, different R 1 substituents on 112 were investigated with alkyl, aryl, heteroaryl and polyaromatic groups giving the corresponding products from low to high yields. The introduction of halogen atoms on the R 2 groups had no influence on the reaction.…”

Section: Cyclic Derivativesmentioning

confidence: 99%

Light‐Induced Domino and Multicomponent Reactions: How to Reach Molecular Complexity without a Catalyst

Renzi,

Scarfiello,

Lanfranco

et al. 2023

Eur J Org Chem

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Achieving high molecular complexity can be not trivial, but the exploitation of domino reactions provides an atom‐ and step‐economical method to reach this target. Over the past decades, a lot of efforts have been put on the development of photocatalytic cascades employing both metal‐based and purely organic catalysts. Despite the effectiveness of these protocols, catalyst‐ and additive‐free light‐induced domino reactions are gaining momentum thank to their efficiency, operational simplicity and sustainability. The increasing number of papers published on this field in the last years is a proof of the appeal of these transformations. In this Review, we discuss domino and multicomponent reactions mediated by light with a focus on photocatalyst‐ and additive‐free processes. The most recent advances in the synthesis of complex nitrogen‐, oxygen‐, sulphur/selenium‐heterocycles together with multicomponent cascades are analysed with an emphasis on both experimental and mechanistic studies.

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Section: Cyclic Derivativesmentioning

confidence: 99%

Light‐Induced Domino and Multicomponent Reactions: How to Reach Molecular Complexity without a Catalyst

Renzi,

Scarfiello,

Lanfranco

et al. 2023

Eur J Org Chem

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A highly diastereoselective one-pot Ugi/radical spirocyclization/aza-Michael addition sequence

Khan,

Chatterjee,

Nair

et al. 2024

Org. Biomol. Chem.

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Recent Advances in the Light-assisted Synthesis of Ring Junction Nitrogen Heterocycles

Kumar,

Aravindraj,

Madhumitha

et al. 2023

COC

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Nitrogen ring junction heterocycles play a crucial role in synthetic organic chemistry due to their remarkable activity. The fused nitrogen ring junction compounds are abundant in nature; they have excellent biological activity and are used against various health issues. To make selective nitrogen ring junction products from the nitrogen ring junction heterocycles, , expensive chemicals and catalysts, like expensive transition metal complexes and metal composites, are required. To neglect the drawbacks of conventional synthesis methods like long reaction times, by-product formation, lower selectivity, and low yields, an alternative of non-conventional light-mediated techniques can be opted for. The light source uses a radical mechanism that reduces by-product formation, provides a regio-selective product, increases yield, decreases reaction time, is cost-effective, and does not require special catalysts or chemicals. There are a variety of light sources, viz., UV, visible, IR, laser, and X-ray. The UV, visible light, white, green, and blue LED light sources are widely used in the photochemical method. This review emphasizes the light-mediated synthesis of nitrogen-ring junction heterocyclic compounds.

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Synthesis of sulfur-containing benzo[b]pyrrolo[2,1-c][1,4]oxazine-3,9-diones: blue light promoted radical cyclization process

Abstract: In this work, a general and convenient protocol for the blue light-promoted radical-mediated cascade spiro-cyclization/Michael addition of N-arylpropiolamides with thiophenols under metal-free conditions was developed.

Cited by 3 publications

References 61 publications

Light‐Induced Domino and Multicomponent Reactions: How to Reach Molecular Complexity without a Catalyst

Light‐Induced Domino and Multicomponent Reactions: How to Reach Molecular Complexity without a Catalyst

A highly diastereoselective one-pot Ugi/radical spirocyclization/aza-Michael addition sequence

Recent Advances in the Light-assisted Synthesis of Ring Junction Nitrogen Heterocycles

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