Three component coupling reactions of N-acetyl-2-azetine- rapid stereoselective entry to 2,3,4-trisubstituted tetrahydroquinolines.

doi:10.1039/B110242G

Paper

Three component coupling reactions of N-acetyl-2-azetine- rapid stereoselective entry to 2,3,4-trisubstituted tetrahydroquinolines.

Published Feb 27, 2002 · P. Stevenson, M. Nieuwenhuyzen, Daire Osborne

Chemical communications

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27

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0

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Abstract

N-Acetyl-2-azetine undergoes Lewis acid catalysed [4 + 2]-cycloaddition with imines derived from aromatic amines and gave a 1:1 mixture of exo-endo diastereoisomeric azetidine cycloadducts which reacted further with aromatic amine, to give 2,3,4-trisubsitituted tetrahydroquinolines in good to excellent yield, predominantly as one diastereoisomer.

Study Snapshot

N-acetyl-2-azetine undergoes rapid stereoselective entry to 2,3,4-trisubstituted tetrahydroquinolines through Lewis acid catalysis with aromatic amines, yielding good to excellent yields of 2,3,4-trisubstituted

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Three component coupling reactions of N-acetyl-2-azetine- rapid stereoselective entry to 2,3,4-trisubstituted tetrahydroquinolines.

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References

Citations

The (±)-5-Aza[1.0]triblattane Skeleton via Azetine Cycloaddition.

The 5-aza[1.0]triblattane skeleton was synthesized using azetine cycloaddition, but it is more unstable than the 6-aza isomer under acidic conditions.

Forging C−S Bonds on the Azetidine Ring by Continuous Flow Photochemical Addition of Thiols and Disulfides to Azetines

Continuous flow photochemical addition of thiols and disulfides to azetines efficiently forges C-S bonds, providing fast, robust, and scalable protocols with environmentally responsible solvents.

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

New synthetic methods have made 1- and 2-azetines more accessible, offering potential as reactive intermediates for accessing other heterocycles and complex products.

Endocyclic Enamides Derived from Aza‐Diketopiperazines as Olefin Partners in Povarov Reaction: An Access to Tetracyclic N‐Heterocycles

Endocyclic enamides derived from aza-diketopiperazines can be used as dienophile partners in the Povarov reaction, enabling the structural diversification of the aza-DKP scaffold and access to new fused tetracyclic N-heterocycles

trans-Selective Aryldifluoroalkylation of Endocyclic Enecarbamates and Enamides via Nickel Catalysis.

Nickel-catalyzed trans-selective dicarbofunctionalization of N-Boc-2-pyrroline and N-Boc-2-azetine allows for efficient synthesis of fluorinated pyrrolidine- and azetidine-containing amino acids and oligo

Silver-catalyzed cyclization of nitrones with 2-azetine: a radical approach to 2,3-disubstituted quinolines

Silver-catalyzed intermolecular tandem cyclization of nitrones with 2-azetine effectively synthesizes 2,3-disubstituted quinolines under mild conditions with good yields.

Step-Controlled Povarov-Type Reaction with 1,2-Dihydroquinolines as Precursors of Dienophiles: Direct Synthesis of Spirocyclic Bi-tetrahydroquinolines and Functionalized 1,2-Dihydroquinolines.

The developed Povarov-type reaction allows for the straightforward synthesis of novel spiro bi-tetrahydroquinolines and functionalized 1,2-DHQs, with potential applications in the synthesis of dienophiles.

Convergence of products from Povarov and von Miller reactions: approaches to helquinoline

Yttrium triflate or triflic acid catalyzed Povarov reaction of methyl anthranilate with ethyl vinyl ether produces 2-methyl-4-ethoxytetrahydroquinoline diastereoisomers and von Miller adducts,