Silver-Assisted [3 + 2] Annulation of Nitrones with Isocyanides: Synthesis of 2,3,4-Trisubstituted 1,2,4-Oxadiazolidin-5-ones

Shen, Xuanyu; Shatskiy, Andrey; Chen, Yan; Kärkäs, Markus D.; Wang, Xiang‐Shan; Liu, Jian‐Quan

doi:10.1021/acs.joc.9b03279

Cited by 19 publications

(5 citation statements)

References 43 publications

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“…Kärkäs, Liu and co‐workers reported a [3+2] cycloaddition of nitrones 111 with isocyanides 112 affording a variety of 2,3,4‐trisubstituted 1,2,4‐oxadiazolidin‐5‐one derivatives 113 as single diastereomers in good to excellent yields using silver oxide as the catalyst and molecular oxygen as the terminal oxidant (Scheme 13a) [24] . A cascade mechanistic pathway of nucleophilic addition/cyclization/protodeargentation/oxidation was proposed, as shown in Scheme 13b.…”

Section: Synthesis Of Five‐membered Heterocyclic Compoundsmentioning

confidence: 99%

Silver‐Catalyzed and Silver‐Promoted Reactions of Isocyanides

Wang

Zhang

et al. 2023

Eur J Org Chem

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In recent years, the silver‐catalyzed and silver‐promoted isocyanide reactions have attracted much attention, due to its efficiency in the formation of diverse new bonds and good reaction selectivity. A series of highly useful linear or cyclic compounds have been constructed. In this review, the recent progress in this field is described in the sequence of synthesis of five‐membered heterocyclic compounds, synthesis of six‐membered heterocyclic compounds, synthesis of fused cyclic compounds as well as synthesis of linear nitrogen‐containing compounds.

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Section: Synthesis Of Five‐membered Heterocyclic Compoundsmentioning

confidence: 99%

Silver‐Catalyzed and Silver‐Promoted Reactions of Isocyanides

Wang

Zhang

et al. 2023

Eur J Org Chem

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“…In 2020, Kärkäs, Liu and co-workers developed a silver-assisted method for the [3 + 2] cycloaddition of isocyanides with nitrones 25 (Scheme 7). 25 The developed protocol allowed access to a variety of 1,2,4-oxadiazolidin-5-one derivatives 27 as single diastereomers in good to excellent yields. In the process, a stepwise cycloaddition is proposed, and the cycloaddition provides a key intermediate 29 .…”

Section: Cyclization With 13-dipolarsmentioning

confidence: 99%

Catalytic metal-enabled story of isocyanides for use as “C1N1” synthons in cyclization: beyond radical chemistry

Chen

Wang

et al. 2022

Org. Chem. Front.

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“…Kärkäs, Liu, and co-workers developed a [3+2] annulation of nitrones 161 and isocyanides to yield a variety of 2,3,4-trisubstituted 1,2,4-oxadiazolidin-5-one derivatives 164 (Scheme 50). 112 The reaction was carried out by using silver oxide as the catalyst and molecular oxygen as the terminal oxidant. Based on empirical results a mechanism was proposed that includes a nucleophilic addition/cyclization/protodeargentation/oxidation pathway.…”

Section: Special Topic Synthesismentioning

confidence: 99%

Transition Metal and Inner Transition Metal Catalyzed Amide Derivatives Formation through Isocyanide Chemistry

et al. 2020

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The synthesis of amides is a substantial research area in organic chemistry because of their ubiquitous presence in natural products and bioactive molecules. The use of easily accessible isocyanides as amidoyl (carbamoyl) synthons in cross-coupling reactions using transition metal and inner transition metöal catalysts is a current trend in this area. Isocyanides, owing to their coordination ability as a ligand and inherent electronic properties for reactions with various partners, have expanded the potential application of these transformations for the preparation of novel synthetic molecules and pharmaceutical candidates. This review gives an overview of the achievements in isocyanide-based transition metal and inner transition metal catalyzed amide formation and discusses highlights of the proposed distinct mechanisms.1 Introduction2 Synthesis of Arenecarboxamides3 Synthesis of Alkanamides4 Synthesis of Cyclic Amides5 Formation of Alkynamides6 Formation of Acrylamide-like Molecules7 Formation of Ureas and Carbamates8 Conclusion

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Silver-Assisted [3 + 2] Annulation of Nitrones with Isocyanides: Synthesis of 2,3,4-Trisubstituted 1,2,4-Oxadiazolidin-5-ones

Cited by 19 publications

References 43 publications

Silver‐Catalyzed and Silver‐Promoted Reactions of Isocyanides

Silver‐Catalyzed and Silver‐Promoted Reactions of Isocyanides

Catalytic metal-enabled story of isocyanides for use as “C1N1” synthons in cyclization: beyond radical chemistry

Transition Metal and Inner Transition Metal Catalyzed Amide Derivatives Formation through Isocyanide Chemistry

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