Diazo‐Based Construction of Heterocyclic Systems Via a X−H Insertion/Cyclization Cascade DOI Open Access
Ksenia Malkova, Dmitry Dar’in

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 30, 2024

Abstract The X−H insertion reaction (X=heteroatom) of diazo compounds has emerged as an eminent and reliant approach for the construction C−X bonds. By merging with sequential ring‐closing transformations, diverse heterocyclic systems can be obtained in a step‐economical manner. In recent years, insertion/cyclization cascades one‐pot transformations attract more research attention, especially area asymmetric synthesis. Concentrating on assembly N,O,S‐heterocycles, this Concept elucidates various combinations reactions cyclization via addition to multiple ring‐forming strategies reviewed comprise Michael‐type Conia‐ene reactions, aldol condensation, Mannich reaction.

Language: Английский

Photochemical Functionalization of 4-Diazoisoquinoline-1,3(2H,4H)-diones and Their 1-Sulfoxide Analogues DOI Creative Commons
Joseph P. Milton, Dorota Gryko

ACS Organic & Inorganic Au, Journal Year: 2025, Volume and Issue: unknown

Published: March 24, 2025

Language: Английский

Citations

0
Entry to new spiroheterocycles via tandem Rh(II)-catalyzed O–H insertion/base-promoted cyclization involving diazoarylidene succinimides DOI Creative Commons
Alexander Yanovich,

Anastasia Vepreva,

Ksenia Malkova

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 561 - 569

Published: March 11, 2024

A facile approach to novel medicinally relevant spiro heterocyclic scaffolds (namely furan-2(5 H )-ones, tetrahydrofurans and pyrans spiro-conjugated with the succinimide ring) has been developed. The protocol consists of Rh(II)-catalyzed insertion carbenes derived from diazoarylidene succinimides (DAS) into O–H bond propiolic/allenic acids or brominated alcohols, followed by base-promoted cyclization afford target spirocyclic compounds in good high yields.

Language: Английский

Citations

1
Rhodium-catalyzed transformations of diazo compounds via a carbene-based strategy: recent advances DOI Creative Commons
Fatemeh Doraghi,

Parsa Baghershahi,

Mehran Ghasemi

et al.

RSC Advances, Journal Year: 2024, Volume and Issue: 14(53), P. 39337 - 39352

Published: Jan. 1, 2024

As a carbene precursor, diazo compounds incorporate in Rh-catalyzed synthesis of heterocycles, carbocycles and functionalized compounds. The reaction involves C–H activation, insertion an annulation/functionalization sequence.

Language: Английский

Citations

1
Substrate-Controlled Regioselective Cascade Reactions of Deconjugated Butenolides and Cinnamaldehydes: Access to Structurally Diverse Spirobutenolides DOI

Juan-Ru Tian,

Hang Qin, Lanbo Liu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 3, 2024

Two different cascade pathways to access spirobutenolides were achieved based on the substrate-controlled regioselectivity of deconjugated butenolides. A new class functional butenolides was designed and exhibited superior γ-regioselectivity in vinylogous Michael/Michael reactions with cinnamaldehydes. The aryl-substituted cinnamaldehydes underwent a Michael/Michael/aldol/dehydration process induced by double α-regioselectivities. Both conjugated could be obtained good yields excellent enantioselectivities.

Language: Английский

Citations

0
Diazo‐Based Construction of Heterocyclic Systems Via a X−H Insertion/Cyclization Cascade DOI Open Access
Ksenia Malkova, Dmitry Dar’in

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 30, 2024

Abstract The X−H insertion reaction (X=heteroatom) of diazo compounds has emerged as an eminent and reliant approach for the construction C−X bonds. By merging with sequential ring‐closing transformations, diverse heterocyclic systems can be obtained in a step‐economical manner. In recent years, insertion/cyclization cascades one‐pot transformations attract more research attention, especially area asymmetric synthesis. Concentrating on assembly N,O,S‐heterocycles, this Concept elucidates various combinations reactions cyclization via addition to multiple ring‐forming strategies reviewed comprise Michael‐type Conia‐ene reactions, aldol condensation, Mannich reaction.

Language: Английский

Citations

0