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α-Sulfonylated ketazine synthesis from vinyl azides and sodium sulfinates using CAN: Radical C-S/N-N coupling cascade as a key reaction pathway

Organic Chemistry Frontiers
Synthesis of α-sulfonylated ketazines from vinyl azides and sodium sulfinates proceeding via radical C-S/N-N coupling cascade has been developed.
M. M. Doronin   +6 more
semanticscholar   +1 more source

Brønsted Acid-Catalyzed Synthesis of 1,2,5-Trisubstituted Imidazoles via a Multicomponent Reaction of Vinyl Azides with Aromatic Aldehydes and Aromatic Amines.

Journal of Organic Chemistry, 2022
A facile and efficient approach to the synthesis of 1,2,5-trisubstituted imidazoles is developed via a multicomponent reaction under metal-free catalysis.
Jiu-Qin Li   +8 more
semanticscholar   +1 more source

Additive-free synthesis of α-keton thiol esters via oxyacylthiolation of vinyl azides with thioacids and water.

Chemical Communications
An additive-free strategy has been developed for the synthesis of α-keton thiol esters through direct oxyacylthiolation of vinyl azides with thioacids and water. The C-S and CO bonds were formed in a one-pot operation via a radical reaction pathway.
Yingjie Wang   +7 more
semanticscholar   +1 more source

Radical borylation of vinyl azides with NHC-boranes: divergent synthesis of α-boryl ketones and borylated triazoles.

Organic and biomolecular chemistry, 2022
A divergent radical borylation of vinyl azides with N-heterocyclic carbene (NHC) boranes in the presence of tBuSH is described. The protocol enables the divergent synthesis of α-boryl ketones and borylated triazoles with excellent functional group ...
Yifei Zhang   +4 more
semanticscholar   +1 more source

Cu(II)‐Catalyzed Asymmetric All‐Carbon‐Based Diels–Alder Reaction of Conjugated Vinyl Azides: Synthesis of Chiral Fused and Spiro Cyclohexenes

Advanced Synthesis & Catalysis
A highly diastereo‐ and enantioselective all‐carbon‐based Diels–Alder reaction of conjugated vinyl azides with β,γ‐unsaturated α‐keto esters and amides was achieved. With C1‐symmetric imidazolidine‐pyrroloimidazolone pyridine as the tridentate ligand and
Ning Li   +5 more
semanticscholar   +1 more source

Mn- and DMAP-Promoted Formal [3 + 2]-Cycloaddition of Cyanoacetates and Malonates with Vinyl Azides for the Synthesis of α-Quaternary Ene-γ-Lactams.

Journal of Organic Chemistry
A Mn- and DMAP-promoted [3 + 2]-cycloaddition of cyanoacetates and malonates with vinyl azides was presented, enabling the concise synthesis of α-quaternary ene-γ-lactam.
Xuanfeng Li   +9 more
semanticscholar   +1 more source

Synthesis of thiazoles from vinyl azides and xanthates under the action of an Mn(III)-oxidant.

Organic and biomolecular chemistry
Reaction of xanthates and vinyl azides under the action of Mn(OAc)3 results in the formation of alkoxy thiazoles. In this transformation, potassium xanthate undergoes Mn-mediated oxidation, generating the corresponding xanthyl radical.
L. A. Zaikina   +6 more
semanticscholar   +1 more source

Iridium-Catalyzed Highly Enantioselective and Chemodivergent Coupling Reaction of Vinyl Azides and Vinyl Benzoxazinones

Organic Chemistry Frontiers
The first Iridium-catalyzed enantioselective coupling reaction of vinyl azides and vinyl benzoxazinones is presented. Vinyl azides underwent a tandem allylic alkylation/interrupted Schmidt rearrangement process to produce enantioenriched 3,4 ...
Deli Gan   +9 more
semanticscholar   +1 more source

Efficient Transition Metal‐Free Potassium Persulfate Promoted Regioselective Ketonization of Vinyl Azides: Advancing α‐Thiocyanated Ketones Synthesis

Asian Journal of Organic Chemistry
The development of a highly effective regioselective ketonization of vinyl azides advancing α‐thiocyanated ketones without transition metals using potassium persulfate as a promoter represents a significant milestone in organic synthesis. This innovative
Santosh Sing Sardar   +3 more
semanticscholar   +1 more source

Reactions of Vinyl Azides

Angewandte Chemie International Edition in English, 1975
AbstractThis review is designed to demonstrate the versatility of vinyl azides in organic reactions. The reactive azide function is susceptible to thermolysis, photolysis, cycloadditions, and attack by nucleophiles and electrophiles. The neighboring double bond accentuates the reactivity of the azide function and provides additional intramolecular ...
openaire   +1 more source

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