Green synthesis of polysubstituted pyrroles through a domino sequence of aza-Claisen rearrangement/nucleophilic addition/oxidation/acylation DOI
Alexandra S. Golubenkova, Никита Е. Голанцов, А. В. Варламов

и другие.

AIP conference proceedings, Год журнала: 2022, Номер 2390, С. 020019 - 020019

Опубликована: Янв. 1, 2022

A pseudo three-component reaction of 2-imidazolines with electron-deficient alkynes furnishes 1,2,2,3-tetrasubstituted imidazolidines containing N-vinylpropargylamine moiety. Heating in aerobic conditions butyl acetate solution leads to highly functionalized pyrroles through aza-Claisen rearrangement/nucleophilic addition/oxidation/acylation.

Язык: Английский

X‐yne click polymerization DOI Creative Commons

Xinyao Fu,

Anjun Qin, Ben Zhong Tang

и другие.

Aggregate, Год журнала: 2023, Номер 4(5)

Опубликована: Май 6, 2023

Abstract Alkyne‐based click polymerizations have been nurtured into a powerful synthetic technique for the preparation of new polymers with advanced structures and versatile properties. Among them, emerging thiol‐yne, hydroxyl‐yne, amino‐yne made remarkable progress from reactions to applications. These avoid usage inherently dangerous monomers are safer operate than classical azide‐alkyne polymerization (AACP), making them more prospective diverse To greatly promote alkyne‐based beyond AACP, concept “X‐yne polymerization” is proposed unify where “X” denotes that can react alkynes under mild reaction conditions, including thiols, alcohols, amines, other promising ones. In this review, we mainly present brief account X‐yne discuss in detail challenges opportunities field.

Язык: Английский

Процитировано

60

The chemistry of heterocycles in the 21st century DOI
Valery N. Charushin, Egor V. Verbitskiy, О. Н. Чупахин

и другие.

Russian Chemical Reviews, Год журнала: 2024, Номер 93(7), С. RCR5125 - RCR5125

Опубликована: Июль 1, 2024

The chemistry of heterocyclic compounds has traditionally been and remains a bright area chemical science in Russia. This is due to the fact that many heterocycles find widest application. These are key structural fragments most drugs, plant protection agents. Many natural also derivatives heterocycles. At present, more than half hundreds millions known collective review devoted achievements Russian chemists this field over last 15–20 years. presents leading heterocyclists representing both RAS institutes university science. It worth noting wide scope review, terms geography author teams, covering whole our large country, diversity research areas. Practically all major types represented review. special attention focused on practical applications design new drugs biologically active compounds, high-energy molecules, materials for organic electronics photovoltaics, ligands coordination chemistry, other rapidly developing advances would not be possible without development fundamental transformations chemistry.<br> Bibliography — 2237 references.

Язык: Английский

Процитировано

35

Pd-Catalyzed Triple-Fold C(sp2)–H Activation with Enaminones and Alkenes for Pyrrole Synthesis via Hydrogen Evolution DOI
Leiqing Fu, Yunyun Liu, Jie‐Ping Wan

и другие.

Organic Letters, Год журнала: 2021, Номер 23(11), С. 4363 - 4367

Опубликована: Май 20, 2021

The synthesis of NH-free pyrroles via Pd-catalyzed annulation enaminones and alkenes is reported. With the catalysis Pd(II), activation triple C(sp2)-H bonds, including one internal bond in enaminone, has been activated to provide various pyrroles. interesting evolution hydrogen gas from reactions observed by a detector.

Язык: Английский

Процитировано

66

Recent advances in the syntheses of pyrroles DOI Creative Commons
Tao Shi,

Gaofeng Yin,

Xiaodong Wang

и другие.

Green Synthesis and Catalysis, Год журнала: 2022, Номер 4(1), С. 20 - 34

Опубликована: Июнь 23, 2022

The pyrrole moiety is an important structural motif in functional materials, natural products, and pharmaceuticals. More more synthetic strategies toward pyrroles have emerged, where various efficient building blocks are developed these synthons enable the syntheses of with different numbers components. However, no review specifically summarizes according to type number employed blocks. To aid researchers design appropriate substrates for synthesis, herein we summarized advances classified reactions into four categories components, which may shed light on developing methods substituted pyrroles.

Язык: Английский

Процитировано

46

Synthesis of Tetrasubstituted Pyrroles via DBU-Mediated Cyclization of Unactivated Propargyl Tertiary Amines DOI
Pengyu Zhou, Tiantian Zhang, Q. Richard Lu

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 10, 2025

Compared with the well-developed cyclization of functionalized propargylamines, use unactivated tertiary propargylamines to access pyrroles remains challenging. Herein, we report an efficient method for constructing tetrasubstituted via a DBU-mediated intramolecular cycloaddition N-alkyl propargylamines. This reaction employs dihydropyrrole intermediates, followed by oxidation produce in presence 2,3-dichloro-5,6-dicyano-p-benzoquinone. In addition, broad substrate scope, high atom economy, selectivity, and simple operation are also advantages this protocol.

Язык: Английский

Процитировано

0

Recent advances in metal-free catalysts for the synthesis of N-heterocyclic frameworks focusing on 5- and 6-membered rings: a review DOI Creative Commons
Hai Truong Nguyen,

The Thai Nguyen,

Vinh Thanh Chau Doan

и другие.

RSC Advances, Год журнала: 2025, Номер 15(13), С. 9676 - 9755

Опубликована: Янв. 1, 2025

The tremendous potential of transition metal-free multi-component reactions (MCR) in the synthesis N-heterocyclic frameworks is examined this review, offering a complete overview subject matter. discussion on mechanistic rationale reaction routes and intermediates provides profound insights into underlying changes, encouraging deeper investigation various molecular frameworks. This review serves as doorway to study practicality exploiting these for efficient uncomplicated specific nitrogen heterocycles. Specifically, we reveal catalysts field. Because their extensive scope diversity, enable heterocycles that contain nitrogen, which include 5-membered (carbazole, pyrimidines, pyrroles) 6-membered rings (piperidine, pyridine, quinoline, diazinane, pyrazine, quinoxaline, 1,2,3-triazine). In addition, compatibility with functional groups substrates not only increases synthetic value compounds but also broadens relevance domains medical chemistry, materials science, other relevant areas study. To motivate future development field, successful examples described highlight powerful instruments quick general, thorough insightful examination catalysts, highlighting contemporary organic revolutionize field heterocycle synthesis.

Язык: Английский

Процитировано

0

Solvent and Water Enabled Control of Alkyne-Base Polymerization Triggered by a Spontaneous Imine-Yne Click Reaction DOI
Jie Chen, Xinyu Xu, Qing Xia

и другие.

Macromolecules, Год журнала: 2024, Номер 57(5), С. 1970 - 1978

Опубликована: Фев. 22, 2024

The control of the polymer structure is a pivotal factor in imparting wide range desirable properties to polymers. However, existing methods often entail harsh conditions and laborious procedures. In this study, we demonstrate that solvent water play crucial role facile regulation cyclic imidazolidine linear dienamine units chains produced by polymerization imidazolines ester alkynes, which was triggered spontaneous imine-yne click reaction. Notably, when carried out acetonitrile, yielded polymers predominantly feature structures (up 96%), whereas those synthesized chloroform presence are characterized 91%). These structural variances give rise diverse polymers, including variations glass transition temperatures, Raman signals, nontraditional luminescence, refractive indices, etc. Moreover, reaction mechanism unambiguously proposed based on model studies, shedding light underlying chemical processes driving these distinct results. ability through solvents offers promising avenue for tailoring properties, unlocking new opportunities advanced materials design.

Язык: Английский

Процитировано

3

Catalytic asymmetric interrupted Attanasi reaction: access to fused 2,3-dihydropyrroles with vicinal quaternary carbons DOI

Yun‐Xuan Chen,

Tian‐Jiao Han,

Xiao Xiao

и другие.

Chemical Communications, Год журнала: 2023, Номер 59(52), С. 8103 - 8106

Опубликована: Янв. 1, 2023

The first catalytic asymmetric interrupted Attanasi reaction has been established. Under the catalysis of a bifunctional organocatalyst, condensation cyclic β-keto esters with azoalkenes readily occurred, delivering variety bicyclic fused 2,3-dihydropyrroles vicinal quaternary stereogenic centers in good yields and to excellent enantioselectivities (27 examples, up 96% yield 95% ee).

Язык: Английский

Процитировано

8

Direct Access to 4-Substituted Isoquinolones via a Sequential Pd-Catalyzed Cyclization/Base-Promoted Aromatization/Ring-Opening of N-Propargyl-1,3-oxazolidines DOI

Xianjun Xu,

Liangliang Song, Huangdi Feng

и другие.

Molecular Catalysis, Год журнала: 2022, Номер 522, С. 112231 - 112231

Опубликована: Март 17, 2022

Язык: Английский

Процитировано

9

Amine-catalyzed metal-free deamination of propargylamines with water toward chalcones DOI
Pengyu Zhou, Liliang Huang,

Yujuan Xie

и другие.

Molecular Catalysis, Год журнала: 2022, Номер 534, С. 112808 - 112808

Опубликована: Ноя. 18, 2022

Язык: Английский

Процитировано

9