Recent Advances in the Light-assisted Synthesis of Ring Junction Nitrogen Heterocycles DOI

Periasamy Vinoth Kumar,

Kumar Aravindraj,

Gunabalan Madhumitha

et al.

Current Organic Chemistry, Journal Year: 2023, Volume and Issue: 27(12), P. 997 - 1009

Published: June 1, 2023

Abstract: Nitrogen ring junction heterocycles play a crucial role in synthetic organic chemistry due to their remarkable activity. The fused nitrogen compounds are abundant nature; they have excellent biological activity and used against various health issues. To make selective products from the heterocycles, expensive chemicals catalysts, like transition metal complexes composites, required. neglect drawbacks of conventional synthesis methods long reaction times, by-product formation, lower selectivity, low yields, an alternative nonconventional light-mediated techniques can be opted for. light source uses radical mechanism that reduces provides regio-selective product, increases yield, decreases time, is cost-effective, does not require special catalysts or chemicals. There variety sources, viz., UV, visible, IR, laser, X-ray. visible light, white, green, blue LED sources widely photochemical method. This review emphasizes nitrogen-ring heterocyclic compounds.

Language: Английский

Palladium-Catalyzed Allylation of Endocyclic 1-Azaallyl Anions DOI
Xiaoyu Yang, Biao Zhang,

Junhao Ruan

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8896 - 8905

Published: June 10, 2024

Endocyclic 1-azaallyl anions engage allyl acetates in a palladium-catalyzed allylation followed by reduction to give unprotected 2-(hetero)aryl-3-allylpiperidines and 2-allyl-3-arylmorpholines, products not easily accessible other means. The group is then readily transformed into variety of functional groups. Preliminary studies on the asymmetric variant reaction using an enantiomerically pure BI-DIME-type ligand provide product with moderate enantioselectivity. Computational suggest that energy barriers inner-sphere reductive elimination outer-sphere nucleophilic substitution are almost same, which makes both them possible pathways. In addition, mechanism displays enantiodiscriminating C–C bond forming step, while much less selective, combined

Language: Английский

Citations

1

Direct Thioamination of Cyclohexanones via Difunctionalization with Thiophenol and Aniline DOI

Minli Tang,

Li Zhang, Guojiang Mao

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(13), P. 2205 - 2210

Published: May 20, 2022

Abstract A synthetic method of o ‐sulfanylanilines from cyclohexanones, amines, and thiophenols under transition‐metal‐free conditions is disclosed. This the first report on direct thioamination cyclohexanones via N ‐iodosuccinimide (NIS) promoted oxidative dehydroaromatization. Non‐aromatic were smoothly dehydrogenated, acted as an aryl source using oxygen a green oxidant. The capacity resultant for synthesis ‐arylphenothiazines has been further demonstrated. magnified image

Language: Английский

Citations

7

A facile synthesis of α,β-unsaturated imines via palladium-catalyzed dehydrogenation DOI Creative Commons
Chunyang Zhao, Rong-Wan Gao,

Wenxuan Ma

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: May 21, 2024

Abstract The dehydrogenation adjacent to an electron-withdrawing group provides efficient access α , β -unsaturated compounds that serving as versatile synthons in organic chemistry. However, the -desaturation of aliphatic imines has hitherto proven be challenging due easy hydrolysis and preferential dimerization. Herein, by employing a pre-fluorination palladium-catalyzed reaction sequence, abundant simple amides are amendable rapid construction complex molecular architectures produce imines. Mechanistic investigations reveal Pd(0)/Pd(II) catalytic cycle involving oxidative H–F elimination N -fluoroamide followed smooth in-situ generated imine intermediate. This protocol exhibits excellent functional tolerance, even carbonyl groups compatible without any competing dehydrogenation, allowing for late-stage functionalization bioactive molecules. synthetic utility this transformation been further demonstrated diversity-oriented derivatization concise formal synthesis (±)-alloyohimbane.

Language: Английский

Citations

1

Reusable Ni‐immobilized MOF Catalyst for Dehydrogenation of N‐heterocycles Under Milder Conditions DOI Open Access
Debasis Banerjee,

Motahar Sk,

Shadab Saifi

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 10, 2024

Herein, we have demonstrated the design and synthesis of a novel Ni-immobilized MOF as heterogeneous catalyst for dehydrogenation N-heterocycles. A series five six-membered N-heteroarenes bearing one or more heteroatoms were synthesized in up to 98 % yield (>33 examples). Late stage functionalization β-glucuronides inhibitor, antimalarial drug quinine, nonsteroidal anti-inflammatory (NSAID) indomethacin obtained under milder reactions conditions. mechanistic studies revealed detection H

Language: Английский

Citations

1

Recent Advances in the Light-assisted Synthesis of Ring Junction Nitrogen Heterocycles DOI

Periasamy Vinoth Kumar,

Kumar Aravindraj,

Gunabalan Madhumitha

et al.

Current Organic Chemistry, Journal Year: 2023, Volume and Issue: 27(12), P. 997 - 1009

Published: June 1, 2023

Abstract: Nitrogen ring junction heterocycles play a crucial role in synthetic organic chemistry due to their remarkable activity. The fused nitrogen compounds are abundant nature; they have excellent biological activity and used against various health issues. To make selective products from the heterocycles, expensive chemicals catalysts, like transition metal complexes composites, required. neglect drawbacks of conventional synthesis methods long reaction times, by-product formation, lower selectivity, low yields, an alternative nonconventional light-mediated techniques can be opted for. light source uses radical mechanism that reduces provides regio-selective product, increases yield, decreases time, is cost-effective, does not require special catalysts or chemicals. There variety sources, viz., UV, visible, IR, laser, X-ray. visible light, white, green, blue LED sources widely photochemical method. This review emphasizes nitrogen-ring heterocyclic compounds.

Language: Английский

Citations

3