DABCO-catalyzed mono- and bisallylation of β,γ-unsaturated ketones with Morita-Baylis-Hillman carbonates DOI
Guizhou Yue,

Biao Du,

Qiumi Wang

et al.

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(35), P. 15446 - 15451

Published: Jan. 1, 2024

Mono- and bisallylation of β,γ-unsaturated ketones with MBH carbonates in the presence DABCO at rt, offered α-2-alkoxycarbonyl, α,α-di(2-alkoxycarbonyl) α,γ-di(2-alkoxycarbonyl) α,β-unsaturated moderate to excellent yields.

Language: Английский

Phosphine-Catalyzed Stereospecific and Enantioselective Desymmetrizative [3+2] Cycloaddition of MBH Carbonates and N-(2-tert-Butylphenyl)maleimides DOI

Jie Hou,

Hao Wei, Ying Chen

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 9068 - 9077

Published: June 1, 2024

Herein, we report an l-valine-derived amide phosphine-catalyzed [3+2] cyclization of MBH carbonates and N-(2-tert-butylphenyl)maleimides via asymmetric desymmetrization. Bicyclic N-aryl succinimide derivatives bearing three continuous chiral centers with a remote C–N atropisomeric chirality were constructed stereospecifically enantioselectively. A wide variety could be employed in this process to deliver highly optically pure moderate excellent yields.

Language: Английский

Citations

6
Chemodivergent Synthesis of Sulfonamide and Sulfones from N-Tosylhydrazones by Switching Catalyst and Temperature DOI

Jingru Jin,

Chunyan Li, Rui Wang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(32), P. 6012 - 6017

Published: Aug. 9, 2023

A catalyst- and temperature-controlled selective synthesis of sulfonamide sulfones from N-tosylhydrazones MBH carbonates has been developed. The use palladium catalysts exclusively leads to products at room temperature, whereas the is dominant for a coupling reaction without catalysis. Importantly, or exhibits high nucleophilicity rather than carbene reactivity in these transformations.

Language: Английский

Citations

4
Tunable Regioselective Allylic Alkylation/Iodination of Imidazoheterocycles in Water DOI

Suvam Paul,

Tathagata Choudhuri,

Sourav Das

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(3), P. 1492 - 1504

Published: Jan. 12, 2024

The switchable roles of allylic alcohol and molecular iodine as reagents catalysts have been demonstrated in the regioselective alkylation iodination imidazoheterocycles employing mixture alcohol-I2. First, we explored catalytic activity for allylation using an aqueous medium. a library other electron-rich heterocycles like indole, pyrazole, 4-hydroxy coumarin, 6-amino uracil has achieved by this methodology. efficiency I2 catalyst N-allylation azoles also demonstrated. Next, shown that could be beneficial under room temperature. Mechanistic studies indicate activation took place probably through halogen bonding, NMR show reaction did not proceed ether formation.

Language: Английский

Citations

1
Squaramide-catalyzed asymmetric regioselective allylic alkylation of 4-aminopyrazolones with Morita–Baylis–Hillman carbonates DOI

Aiqi Xue,

Shiqiang Wei,

Xingfu Wei

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(35), P. 7173 - 7179

Published: Jan. 1, 2023

An efficient squaramide-catalyzed asymmetric allylic alkylation of 4-aminopyrazolones with various MBH carbonates via different pathways has been described. This method provides access to a series pyrazolone derivatives bearing nitrogen-containing quaternary stereocenter in high yields excellent enantioselectivities and regioselectivities under mild conditions. In addition, we utilized the target products construct range bi-heterocyclic skeletons through [3 + 2] cycloadditions. These novel hybrid heterocycles would be promising candidates for drug-discovery programs chemical biology.

Language: Английский

Citations

2
Directed Regioselective Arylation of Imidazo[1,2-a]pyridine-3-carboxamides using Rh(III) catalysis. DOI
Kousar Jahan,

M. SOOD,

Osheen Jain

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(35), P. 7121 - 7127

Published: Jan. 1, 2024

We introduced, for the first time, N -methoxyamide directed proximal C–H bond activation of imidazo[1,2- a ]pyridines C(sp 2 )–C(sp ) formation via transition metal catalysed approach to obtain C-5 arylated ]pyridines.

Language: Английский

Citations

0
Five-membered ring systems: With more than 1 N atom DOI
Larry Yet

Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 211 - 257

Published: Jan. 1, 2024

Language: Английский

Citations

0
Eco-friendly K-10 Clay-Mediated [3 + 3] Spiroannulation of Morita–Baylis–Hillman Adduct of Isatin with Anthracene: Synthesis of Green Fluorophore Compounds DOI Creative Commons

Vadivel Vaithiyanathan,

Sivaprakasam Sivaraman

ACS Omega, Journal Year: 2023, Volume and Issue: 9(1), P. 934 - 941

Published: Dec. 20, 2023

An easy and simple spiroannulation of the Morita–Baylis–Hillman adduct isatin derivatives with anthracene was achieved in moderate-to-good yields (37–75%). The spiroderivatives synthesized this work exhibited green fluorescence properties. reaction occurred metal-free eco-friendly K-10 clay-mediated conditions. final products have multiple structural features such as 3-spirooxindole, fluorophoric anthracene, phenanthracene, phenalene, perylene cores.

Language: Английский

Citations

1
DABCO-catalyzed mono- and bisallylation of β,γ-unsaturated ketones with Morita-Baylis-Hillman carbonates DOI
Guizhou Yue,

Biao Du,

Qiumi Wang

et al.

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(35), P. 15446 - 15451

Published: Jan. 1, 2024

Mono- and bisallylation of β,γ-unsaturated ketones with MBH carbonates in the presence DABCO at rt, offered α-2-alkoxycarbonyl, α,α-di(2-alkoxycarbonyl) α,γ-di(2-alkoxycarbonyl) α,β-unsaturated moderate to excellent yields.

Language: Английский

Citations

0