Halogen cation-promoted and solvent-regulated electrophilic cyclization for the regioselective synthesis of 3-haloquinolines and 3-halospirocyclohexadienones DOI
Jianming Li, Chengxiao Liu, Zihan Zhao

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(11), P. 2440 - 2446

Published: Jan. 1, 2023

A novel approach for the production of halogen cations through reaction halogens with silver ions is described in this paper. On basis, regioselective synthesis 3-haloquinolines and 3-halospirocyclohexadienones realized solvent regulation. The gram-scale compatibility complex substrates demonstrate synthetic potential protocol, which will be an appealing strategy organic synthesis.

Language: Английский

Photo-Thermo-Mechanochemical Approach to Synthesize Quinolines via Addition/Cyclization of Sulfoxonium Ylides with 2-Vinylanilines Catalyzed by Iron(II) Phthalocyanine DOI
Luyao Liu,

Jingyang Lin,

Mingxuan Pang

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(5), P. 1146 - 1151

Published: Feb. 3, 2022

A novel photo-thermo-mechanochemical approach to assembling quinolines catalyzed by iron(II) phthalocyanine has been realized for the first time. This transformation features a cost-efficient catalytic system and operational simplicity, is free of solvent, shows good substrate tolerance, providing green alternative existing thermal approaches. Mechanistic experiments demonstrate that in-situ-formed secondary amine may be key intermediate further cyclization/aromatization process.

Language: Английский

Citations

29

Recent advances in iodine–DMSO mediated C(sp3)–H functionalization of methyl-azaarenes via Kornblum oxidation DOI
Swadhin Swaraj Acharya,

Sagarika Patra,

Liza Mama Barad

et al.

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(17), P. 7614 - 7638

Published: Jan. 1, 2024

In the iodine–DMSO medium, methyl group of azaarenes is converted into aldehyde via Kornblum oxidation and trapped in situ by nucleophiles to create azaarene-linked functionalized scaffolds.

Language: Английский

Citations

7

A Review on Molecular Iodine Catalyzed/Mediated Multicomponent Reactions DOI

Monika,

Chander Chander,

Sita Ram

et al.

Asian Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 12(1)

Published: Nov. 26, 2022

Abstract In multicomponent reactions, three or more reactants combine in one pot to form a product without the isolation of intermediate and most contribute newly formed reducing number steps involved waste generated. Molecular iodine is mild, efficient, relatively nontoxic, inexpensive, commercially available, catalyzes various organic reactions due its Lewis acidic behaviour. The development catalyzed by molecular indeed good green alternative for synthetic chemistry. aim this article review all important reported since 2013 order envisage some new efficient protocols synthesis structurally complex molecules.

Language: Английский

Citations

20

FeCl3/KI‐Catalyzed Tandem Oxidative Cyclization for Switchable Total Synthesis of Luotonin A, B and Derivatives DOI

Song Yingchun,

Ming‐Xuan Wang,

Yun‐Ying Yi

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(6), P. 1348 - 1355

Published: Jan. 13, 2024

Abstract A total synthesis strategy was developed for the of luotonin A, B and their analogues using synergistic FeCl 3 /KI‐catalyzed oxidative cyclization. This protocol utilizes cheap widely available N ‐propargyl 2‐methyl‐quinazolinones arylamines under mild conditions, it has a wide substrate scope high atom economy. Different natural products (luotonin derivatives) can be synthesized via unique switchable approach. Further transformations from to E structural modification demonstrate potential applications this method. Moreover, camptothecin also modified with reported afford hydroxyl‐substituted product.

Language: Английский

Citations

4

α‐Halocarbonyls as a Valuable Functionalized Tertiary Alkyl Source DOI Creative Commons
Takashi Nishikata

ChemistryOpen, Journal Year: 2024, Volume and Issue: unknown

Published: July 11, 2024

Abstract This review introduces the synthetic organic chemical value of α‐bromocarbonyl compounds with tertiary carbons. compound a carbon has been used primarily only as radical initiator in atom transfer polymerization (ATRP) reactions. However, recent development photo‐radical reactions (around 2010), research on use alkyl precursors became popular 2012). As more examples were reported, studied not radicals but also for their applications organometallic and ionic That is, act nucleophiles well electrophiles. The carbonyl group is attractive because it allows skeleton to be converted after reaction, being applied total synthesis. In our survey until 2022, can perform full range necessary synthesis, including multi‐component reactions, cross‐coupling, substitution, cyclization, rearrangement, stereospecific asymmetric α‐Bromocarbonyl have created new trend alkylation, which then had limited reaction patterns focuses how chemistry.

Language: Английский

Citations

4

Iodine and DMSO as Surrogate of Hazardous Metal and Non‐Metal Reagents in Organic Synthesis DOI
Reetu Reetu,

Sangita Kalita,

Sonali Prava Dash

et al.

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(3)

Published: Jan. 17, 2024

Abstract Organic synthesis involves the production of important chemical structures using scalable and cost‐effective methods that are also environmentally friendly. In this review, a detailed analysis use iodine DMSO in various synthetic routes for preparation valuable targets presented. These reduce acceptance on expensive additives reagents, offer more sustainable solution these scaffolds.

Language: Английский

Citations

3

One-Pot Total Synthesis of Natural Products Nitramarine, Nitraridine, and Analogues via a Cascade Oxidation/Pictet–Spengler Condensation/Annulation Process DOI

Song Yingchun,

Wenhui Cao,

Ming‐Xuan Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12832 - 12841

Published: Aug. 9, 2024

A cascade oxidation/Pictet–Spengler condensation/annulation process has been developed for the one-pot total synthesis of nitramarine, nitraridine, and their analogues. The procedure proceeded with easily available quinolines tryptophan derivatives. simple metal-free approach, wide substrate scope, functional group tolerance make it applicable diverse bioactive Furthermore, bioactivity evaluation identified two promising leading compounds 5d 5e potent antitumor proliferative activity against breast cancer cells.

Language: Английский

Citations

3

Deaminative Cyclization of Tertiary Amines for the Synthesis of 2-Arylquinoline Derivatives with a Nonsubstituted Vinylene Fragment DOI
Qinghe Gao,

Yimei Guo,

Zhenhua Sun

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 25(1), P. 109 - 114

Published: Dec. 9, 2022

With triethylamine as a vinylene source, convenient protocol for the regioselective synthesis of β,γ-nonsubstituted 2-arylquinolines from aldehydes and arylamines has been accomplished. The deaminative cyclization is also extended to long-chain tertiary alkylamines, enabling diverse alkyl groups be concurrently installed into pyridine rings. This process demonstrates new conversion pathway simultaneous dual C(sp3)-H bond functionalization amines, wherein transient acyclic enamines generated in situ undergo Povarov reaction.

Language: Английский

Citations

14

Metal-free three-component assemblies of anilines, α-keto acids and alkyl lactates for quinoline synthesis and their anti-inflammatory activity DOI

Lizhu Huang,

Lu Yang,

Jie‐Ping Wan

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(21), P. 4385 - 4390

Published: Jan. 1, 2022

A metal-free three-component protocol for quinoline synthesis is developed by using alkyl lactates, anilines and α-keto acids. In vitro experiments disclose the attractive anti-inflammatory activity of these compounds.

Language: Английский

Citations

12

Generation of azaarene nitrile oxides from methyl azaarenes and t-BuONO enabling the synthesis of furoxans and 1,2,4-oxadiazoles DOI

Xiangjin Zhang,

Jian-Kang Cao,

Junjie Ren

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(4), P. 1121 - 1126

Published: Jan. 1, 2022

A high-efficiency strategy for the synthesis of furoxans and 1,2,4-oxadiazoles has been developed, using tert -butyl nitrite (TBN) as nitrogen source. Azaarene nitrile oxides were generated in situ via methyl azaarenes functionalization.

Language: Английский

Citations

10