1,3‐Dipolar Cycloreversion of 1‐Azetines

Burger, Klaus; Thenn, Willy; Müller, Evi

doi:10.1002/anie.197301551

Cited by 18 publications

(2 citation statements)

References 7 publications

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“…7C) to form a variety of products (122)(123)(124). 118 Irradiation of 1-azetines (120) in benzene with UV light resulted in the reversible [3+1]-cycloelimination of isocyanide to afford nitrile ylides 121. The nitrile ylides (121) were trapped by alcohols, dimethyl acetylenedicarboxylate, or dimethyl maleate or fumarate to provide benzimidic ester (122), 2H-pyrrole (123), or 1-pyrroline (124) products respectively.…”

Section: Synthesis Of Complex Molecules Enabled By Azetinesmentioning

confidence: 99%

New strategies for the synthesis of 1- and 2-azetines and their applications as value-added building blocks

Gatazka

McFee

et al. 2022

Org. Biomol. Chem.

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Section: Synthesis Of Complex Molecules Enabled By Azetinesmentioning

confidence: 99%

New strategies for the synthesis of 1- and 2-azetines and their applications as value-added building blocks

Gatazka

McFee

et al. 2022

Org. Biomol. Chem.

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“…7C) to form a variety of products (115-117). 100 Irradiation of 1-azetines (113) in benzene with UV light resulted in the reversible [3+1]cycloelimination of isocyanide to afford nitrile ylides 114. The nitrile ylides (114) were trapped by alcohols, dimethyl acetylenedicarboxylate, or dimethyl maleate or fumarate to provide benzimidic ester (115), 2H-pyrrole (116), or 1-pyrroline (117) products respectively.…”

Section: Synthesis Of Complex Molecules Enabled By Azetinesmentioning

confidence: 99%

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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Azetidines

Moore

Ayers

1983

Chemistry of Heterocyclic Compounds: A Series of Monographs

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1,3‐Dipolar Cycloreversion of 1‐Azetines

Cited by 18 publications

References 7 publications

New strategies for the synthesis of 1- and 2-azetines and their applications as value-added building blocks

New strategies for the synthesis of 1- and 2-azetines and their applications as value-added building blocks

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

Azetidines

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