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Cation-Promoted Strain-Release-Driven Access to Functionalized Azetidines from Azabicyclo[1.1.0]butanes.

Angewandte Chemie, 2023
Access to 1,3-functionalized azetidines through diversity-oriented approach is highly sought-after for finding new applications in drug-discovery. To this goal, strain-release-driven functionalization of azabicyclo[1.1.0]-butane (ABB) has generated ...
Vandana Jaiswal   +4 more
semanticscholar   +1 more source

Azetidines with All-Carbon Quaternary Centers: Merging Relay Catalysis with Strain Release Functionalization.

Journal of the American Chemical Society, 2023
Given the importance and beneficial characteristics of decorated azetidines in medicinal chemistry, efficient strategies for their synthesis are highly sought after. Herein, we report a facile synthesis of the elusive all-carbon quaternary-center-bearing
Che-Ming Hsu   +9 more
semanticscholar   +1 more source

Synthesis of Azetidines

Journal of Pharmaceutical Sciences, 1971
The synthesis of 3-amino-2-phenylazetidine and the p-chloro analog is reported. The reduction of azetidinones with diborane was investigated and found successful with N-unsubstituted systems. 3-Amino-2-phenylazetidine was found active in vitro against monoamine oxidase.
J N, Wells, O R, Tarwater
openaire   +2 more sources

A Decarboxylative Cross-Coupling Platform To Access 2-Heteroaryl Azetidines: Building Blocks with Application in Medicinal Chemistry.

Organic Letters, 2022
Photoredox-transition metal dual catalysis provides a unique platform for constructing sp3-rich chemical matter. Here, we report a nickel-catalyzed cross-coupling of commercially available or easily prepared redox-active NHP azetidine-2-carboxylates with
James T. Brewster   +6 more
semanticscholar   +1 more source

Enantioselective Synthesis of Azetidines through [3 + 1]-Cycloaddition of Donor-Acceptor Aziridines with Isocyanides.

Organic Letters, 2022
The enantioselective [3 + 1]-cycloaddition of racemic donor-acceptor (D-A) aziridines with isocyanides was first realized under mild reaction conditions using a chiral N,N'-dioxide/MgII complex as catalyst, providing a facile route to enantioenriched exo-
Fengcai Zhang   +4 more
semanticscholar   +1 more source

Recent advances in the synthesis and reactivity of azetidines: strain-driven character of the four-membered heterocycle.

Organic and biomolecular chemistry, 2021
Azetidines represent one of the most important four-membered heterocycles used in organic synthesis and medicinal chemistry. The reactivity of azetidines is driven by a considerable ring strain, while at the same the ring is significantly more stable ...
Haseeb Mughal, M. Szostak
semanticscholar   +1 more source

Development of a Continuous Flow Synthesis of 2-Substituted Azetines and 3-Substituted Azetidines by Using a Common Synthetic Precursor.

Journal of Organic Chemistry, 2021
The generation and functionalization, under continuous flow conditions, of two different lithiated four-membered aza-heterocycles is reported. N-Boc-3-iodoazetidine acts as a common synthetic platform for the genesis of C3-lithiated azetidine and C2 ...
Marco Colella   +6 more
semanticscholar   +1 more source

Novel antibacterial azetidine lincosamides

Bioorganic & Medicinal Chemistry Letters, 2008
The synthesis and evaluation of novel azetidine lincosamides 1 are described. Eleven new (3-trans-alkyl)azetidine-2-carboxylic acids were synthesized via alkylation of N-TBS-4-oxo-azetidine-2-carboxylic acid and subsequent elaboration then coupled to 7-chloro-1-methylthio-lincosamine.
Hardwin, O'Dowd   +9 more
openaire   +2 more sources

Synthesis of 1,3-Aminoalcohols and Spirocyclic Azetidines via Tandem Hydroxymethylation and Aminomethylation Reaction of β-Keto Phosphonates with N-Nosyl-O-(2-bromoethyl)hydroxylamine.

Organic Letters, 2021
An unprecedented tandem α-hydroxymethylation and α-aminomethylation reaction of aromatic cyclic β-keto phosphonates with N-nosyl-O-(2-bromoethyl)hydroxylamine in the presence of DBU base has been developed, affording a range of 1,3-aminoalcohols in good ...
Binyu Wu   +4 more
semanticscholar   +1 more source

Visible light–mediated aza Paternò–Büchi reaction of acyclic oximes and alkenes to azetidines

Science
The aza Paternò–Büchi reaction is a [2+2]-cycloaddition reaction between imines and alkenes that produces azetidines, four-membered nitrogen-containing heterocycles.
E. Wearing   +6 more
semanticscholar   +1 more source

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