Other Fused Azetidines, Azetines and Azetes

Lagoutte, Roman; Lefebvre, Quentin; Salomé, Christophe

doi:10.1016/b978-0-12-818655-8.00161-x

Cited by 2 publications

(8 citation statements)

References 313 publications

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“…Methods for the syntheses of 1-and 2-azetines have been the subject of previous reviews. [54][55][56] Figure 3 provides an overview of new synthetic methods developed since 2018 that include advances in cycloaddition, ring-expansion, and elimination strategies.…”

Section: Synthetic Advances Since 2018mentioning

confidence: 99%

“…4G) to hydrogen gas in the presence of palladium-on-carbon (Pd/C) to produce the desired cis-disubstituted azetidines (57). 51 Both Hodgson and co-workers and Didier and colleagues utilized a similar strategy to hydrogenate various N-Boc-2-azetines (56) giving the respective mono-or disubstituted-azetidine frameworks (57). 42,44 Notably, Doyle and co-workers have synthesized chiral 2-azetines (56) bearing a stereocenter at the carbon substituted with R 3 .…”

Section: Synthesis Of 4-membered Heterocyclesmentioning

confidence: 99%

“…51 Both Hodgson and co-workers and Didier and colleagues utilized a similar strategy to hydrogenate various N-Boc-2-azetines (56) giving the respective mono-or disubstituted-azetidine frameworks (57). 42,44 Notably, Doyle and co-workers have synthesized chiral 2-azetines (56) bearing a stereocenter at the carbon substituted with R 3 . 7 The authors highlighted that Pd/Ccatalyzed hydrogenation of chiral 2-azetines (56) allowed access to chiral azetidines (57), preserving the high enantiomeric excess observed in their initially synthesized 2azetines (56).…”

Section: Synthesis Of 4-membered Heterocyclesmentioning

confidence: 99%

“…Previous reviews have focused on providing overviews of established methods to access 1-and 2azetines. [54][55][56] This comprehensive review will highlight advances made in the area of azetine synthesis since 2018.…”

Section: Introductionmentioning

confidence: 99%

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New Strategies for the Synthesis of 1- and 2-Azetines and Their Applications as Value-Added Building Blocks

Schindler

Gatazka

McFee

et al. 2022

Preprint

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Four-membered nitrogen-containing heterocycles are highly desirable functional groups with synthetic and biological applications. Unsaturated 4-membered N-heterocycles, 1- and 2-azetines, are historically underexplored, but have recently been gaining increased interest due to the development of new synthetic methods to access these compounds, and to their potential as reactive intermediates. This review covers new strategies for the synthesis of 1- and 2-azetines with a particular focus on advances made since 2018. Additionally, the use of these compounds as intermediates to access other heterocycles (3- to 6-membered) and complex products is comprehensively discussed.

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Section: Synthetic Advances Since 2018mentioning

confidence: 99%

Section: Synthesis Of 4-membered Heterocyclesmentioning

confidence: 99%

Section: Synthesis Of 4-membered Heterocyclesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

New Strategies for the Synthesis of 1- and 2-Azetines and Their Applications as Value-Added Building Blocks

Schindler

Gatazka

McFee

et al. 2022

Preprint

View full text Add to dashboard Cite

show abstract

“…[19][20][21][22] The synthetic utility of Dewar photoadducts is reviewed elsewhere. 23,24 Additionally, 2-azetine 8 has been found to be the product of the reaction between a recently discovered inhibitor for bacterial caseinolytic protease (ClpP) and a serine residue in the binding pocket. This product is formed when the inhibitor and the serine form a covalent bond, leading to the formation of the azetine 8 and inhibition of the ClpP enzyme.…”

Section: Introductionmentioning

confidence: 99%