Mild synthesis of isoxazoline derivatives via an efficient [4 + 1] annulation reaction of transient nitrosoalkenes and sulfur ylides

Hua, Ting‐Bi; Liu, Cheng‐Xiong; Hu, Weimin; Wang, Long; Yang, Qing‐Qing

doi:10.1038/s41598-021-81370-w

Cited by 9 publications

(5 citation statements)

References 53 publications

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“…In 2021, Yang et al evolved a novel [4 + 1] annulation reaction between sulfur ylides 331 and α-bromooximes 330 through nitrosoalkenes produced in situ [91]. The operation was carried out through a Michael/ intramolecular O alkylation sequence in basic conditions at room temperature in the existence of a solvent such as CHCl 3 or DMSO (Scheme 67).…”

Section: Reactions With Oximes Produced In Situmentioning

confidence: 99%

“…This method demonstrated a prompt and flexible technique that had the potential to synthesize the biologically relevant isoxazoline derivatives in excellent yields showing high diastereoselectivity. It was hence of great importance, especially in the fields of pharmaceutical and medicinal chemistry (Figure 33) [91].…”

Section: Formation Of Co Bondsmentioning

confidence: 99%

“…Chemo and stereoselective synthesis reactions of sulfur ylides (Xie et al[90]). F I G U R E 3 2 Proposed mechanism for synthesis of 3a.S C H E M E 6 7 Annulation reaction with bromoximes with sulfur ylides (Yang et al[91]). …”

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confidence: 99%

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Recent advance: Sulfur ylides in organic synthesis

Kumar,

Sadaf,

Pamidighantam

et al. 2023

Journal of Heterocyclic Chem

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Sulfur ylides are versatile structures that display various characteristics and participate in a myriad of reactions to produce simple, effective, and sometimes stereoselective reactions toward synthesizing sulfur‐containing compounds. Nonetheless, their fulfillment tremendous developments have been made in this field in the past few decades. In this comprehensive review, luminosity is illuminated on the application of sulfur ylides involved in various domino, cascade annulation reactions, and carbene trapping reagents with chameleonic reactivity. In the past numerous decennary, chemists have used sulfur ylides in solvent‐dependent, rhodium catalyzed, dealkylative intercepted, photochemical reaction, halotrifluoromethylation, benzannulation, amidation various name reactions such as Mizoroki–Heck, Suzuki–Miyaura, and Sommelet–Hauser rearrangements. Moreover, other prime applications include metal catalysis, epoxidation of carbonyl compounds, acylmethylation, cyclomerization, oxidation, and insertion reactions. Additionally, some sulfur ylides are extremely useful structures that play a major role in the synthesis of various medicinally active heterocycles structural motifs. This review article discusses all these reactions, their proposed mechanisms, and their application in the current scenario, at length. This tutorial review concludes by providing a future outlook on the investigation into sulfur ylides and various other compounds synthesized using it have great potential to be used in industries, laboratories, pharmaceutical companies, drug production, clinical use, medicinal chemistry, and agrochemical purposes.

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Section: Reactions With Oximes Produced In Situmentioning

confidence: 99%

Section: Formation Of Co Bondsmentioning

confidence: 99%

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Recent advance: Sulfur ylides in organic synthesis

Kumar,

Sadaf,

Pamidighantam

et al. 2023

Journal of Heterocyclic Chem

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“…It should be noted that the ylide 4 could be generated in situ from the corresponding sulfonium salt 10 or taken in a free form. 26 The method was limited mostly to 3-aryl substituted isoxazolines 31. To overcome this issue, our group proposed an alternative route, in which ene-nitrosoacetals 32 are used as surrogates of NSA (Scheme 13).…”

Section: [4 + 1]-annulations With Sulfur Ylidesmentioning

confidence: 99%

“…It should be noted that the ylide 4 could be generated in situ from the corresponding sulfonium salt 10 or taken in a free form. 26…”

Section: [4 + 1]-annulations With Sulfur Ylidesmentioning

confidence: 99%

Recent advances in the application of ylide-like species in [4 + 1]-annulation reactions: an updated review

2022

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Sequential Formal [4+1]‐Cycloaddition, C−H Functionalization and Suzuki–Miyaura Cross‐Coupling for the Synthesis of Trisubstituted Isoxazolines

et al. 2021

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Suzuki–Miyaura cross‐coupling reaction of 3‐bromomethyl isoxazolines with arylboronic acids was suggested as final C−C bond forming step in convenient diastereoselective route to trisubstituted isoxazolines. The required bromides were readily available from nitroalkenes and sulfonium ylides through an efficient sequence of formal [4+1]‐cycloaddition and C−H functionalization of intermediate isoxazoline N‐oxides. The synthetic utility of the obtained isoxazolines was demonstrated by their conversion into valuable products such as hydroxy ketone, pyrrolidinone, etc.

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Mild synthesis of isoxazoline derivatives via an efficient [4 + 1] annulation reaction of transient nitrosoalkenes and sulfur ylides

Cited by 9 publications

References 53 publications

Recent advance: Sulfur ylides in organic synthesis

Recent advance: Sulfur ylides in organic synthesis

Recent advances in the application of ylide-like species in [4 + 1]-annulation reactions: an updated review

Sequential Formal [4+1]‐Cycloaddition, C−H Functionalization and Suzuki–Miyaura Cross‐Coupling for the Synthesis of Trisubstituted Isoxazolines

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