A Review on Molecular Iodine Catalyzed/Mediated Multicomponent Reactions DOI

Monika,

Chander Chander,

Sita Ram

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2022, Номер 12(1)

Опубликована: Ноя. 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.

Язык: Английский

Ultrasound-Promoted Synthesis of α-Thiocyanoketones via Enaminone C═C Bond Cleavage and Tunable One-Pot Access to 4-Aryl-2-aminothiazoles DOI
Yunyun Liu, Tao Zhang, Jie‐Ping Wan

и другие.

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(12), С. 8248 - 8255

Опубликована: Май 26, 2022

Ultrasound has been successfully employed to promote the thiocyanation of C═C bond in enaminones for synthesis α-thiocyanoketones and 2-aminothiazoles. The reactions with ammonium thiocyanate provide ultrasound irradiation at room temperature. More interestingly, simply further heating vessel after ultrasonic leads selective 2-aminothiazoles an unconventional 4-aryl substructure.

Язык: Английский

Процитировано

30

Formal [4+1] Annulation of Azoalkenes with CF3-Imidoyl Sulfoxonium Ylides and Dual Double Bond Isomerization Cascade: Synthesis of Trifluoromethyl-Containing Pyrazole Derivatives DOI
Yue Sun,

Zuguang Yang,

Shu‐Ning Lu

и другие.

Organic Letters, Год журнала: 2022, Номер 24(37), С. 6822 - 6827

Опубликована: Сен. 9, 2022

A straightforward strategy for the metal-free construction of trifluoromethyl-containing pyrazole derivatives has been achieved from readily available α-halo hydrazones and CF3-imidoyl sulfoxonium ylides. The cascade transformation proceeds through formal [4+1] cycloaddition followed by an unexpected dual double bond isomerization. protocol features mild conditions, easy operation, excellent substrate compatibility, good regioselectivity. synthetic utility is demonstrated scale-up reaction further elaboration obtained products.

Язык: Английский

Процитировано

30

Synthesis of homophthalimide spironaphthalenones through [5 + 1] spiroannulation of aryl/alkenyl enaminones with diazo homophthalimides DOI

Chun Xia Yang,

Xinying Zhang, Xuesen Fan

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(17), С. 4282 - 4288

Опубликована: Янв. 1, 2023

Presented herein is a novel synthesis of homophthalimide spironaphthalenones from the cascade reaction enaminones with diazo homophthalimides.

Язык: Английский

Процитировано

21

Recent Advancement on Selectfluor Mediated Synthesis of Heterocyclic Molecules DOI Open Access
Sukanya Das, Rudra Narayan Das, Tapas Ghosh

и другие.

The Chemical Record, Год журнала: 2025, Номер unknown

Опубликована: Янв. 16, 2025

Abstract Selectfluor, [1‐chloromethyl‐4‐fluoro‐1,4‐diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)], is a highly valuable reagent in contemporary chemistry, serving not only as an electrophilic fluorinating agent but also effective catalyst the synthesis of various pharmaceutically relevant heterocycles. This review article seeks to present comprehensive overview significant heterocyclic ring formations facilitated by selectfluor. Both metal‐free and metal‐catalyzed recent advancement on selectfluor mediated cyclisation processes are discussed this mainly over last eight years (2017‐April 2024).

Язык: Английский

Процитировано

1

Recent Advances in the Use of Dimethyl Sulfoxide as a Synthon in Organic Chemistry DOI
Hao Lü, Tong Zhou, Lifen Peng

и другие.

Topics in Current Chemistry, Год журнала: 2022, Номер 380(6)

Опубликована: Окт. 28, 2022

Язык: Английский

Процитировано

29

Electrochemical Synthesis of Polysubstituted Sulfonated Pyrazoles via Cascade Intermolecular Condensation, Radical–Radical Cross Coupling Sulfonylation, and Pyrazole Annulation DOI
Jiajun Feng, Yuzhi Wang,

Luoyu Gao

и другие.

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(19), С. 13138 - 13153

Опубликована: Сен. 27, 2022

Electrochemical synthesis of polysubstituted sulfonated pyrazoles from enaminones and sulfonyl hydrazides was established under metal-free, exogenous-oxidant-free, mild conditions. By judicious choice different electrochemical reaction conditions, NH2-functionalized or N,N-disubstituted can react with aryl/alkyl to afford tetra- trisubstituted in moderate good yields, respectively. The gram-scale transformation demonstrated the efficiency practicability this synthetic strategy. In addition, NH-pyrazole be obtained via dissociation N-tosyl group. Mechanistic studies reveal that cascade proceeded sequence intermolecular condensation, radical-radical cross coupling sulfonylation, pyrazole annulation.

Язык: Английский

Процитировано

26

Thiazole-5-carbaldehyde Synthesis by Cascade Annulation of Enaminones and KSCN with Dess–Martin Periodinane Reagent DOI
Kang Chen,

Baoli Zhao,

Yunyun Liu

и другие.

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(21), С. 14957 - 14964

Опубликована: Окт. 19, 2022

The Dess-Martin periodinane (DMP) reagent-mediated reactions of tertiary enaminones with potassium thiocyanate for the synthesis thiazole-5-carbaldehydes are developed. product formation involves cascade hydroxyl thiocyanation C═C double bond, intramolecular hydroamination C≡N and thiazole annulation by condensation on ketone carbonyl site, representing novel reaction pathways in between salt. DMP plays dual roles mediating free radical inducing unconventional selective thiazole-5-carbaldehyde masking situ generated formyl group during process.

Язык: Английский

Процитировано

25

Copper-Promoted Aerobic Oxidative [3+2] Cycloaddition Reactions of N,N-Disubstituted Hydrazines with Alkynoates: Access to Substituted Pyrazoles DOI

Xiaoying Zou,

Lvyin Zheng,

Xiaoya Zhuo

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(4), С. 2190 - 2206

Опубликована: Фев. 1, 2023

A copper-promoted aerobic oxidative [3+2] cycloaddition reaction for the synthesis of various substituted pyrazoles from N,N-disubstituted hydrazines with alkynoates in presence bases is developed. This work involves a direct C(sp3)-H functionalization and formation new C-C/C-N bonds. In this strategy, inexpensive easily available Cu2O serves as promoter air acts green oxidant. The exhibits advantages high atom step economy, regioselectivity, easy operation.

Язык: Английский

Процитировано

15

Unlock the C–N Bond Amidation of Enaminones: Metal-Free Synthesis of Enamides by Water-Assisted Transamidation DOI

Haozhi Wu,

Kang Chen, Yunyun Liu

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 89(1), С. 216 - 223

Опубликована: Дек. 18, 2023

The C–N bond transamidation of primary amides with N,N-dimethyl enaminones has been efficiently realized by heating in the presence trifluoromethanesulfonic acid (TfOH). method enables practical synthesis valuable enamides without use any metal reagent. In addition, this protocol can also be expanded to reactions sulfonamides, and late-stage functionalization on sulfonamide drugs such as Celecoxib Valdecoxib verified. Moreover, participation water assisting process identified isotope labeling experiments using D2O, disclosing a new possibility designing catalytic tactic other reactions.

Язык: Английский

Процитировано

14

Photocatalytic Annulation of Enaminones with Thioureas for the Synthesis of 2-Aminothiazoles via Tandem C–S and C–N Bond Formation DOI
Changfeng Wan, Jie‐Ping Wan,

Qihui Huang

и другие.

Synthesis, Год журнала: 2024, Номер 56(16), С. 2565 - 2571

Опубликована: Апрель 26, 2024

Abstract Visible-light photocatalytic reactions between enaminones and thioureas leading to thiazole products have been achieved. The annulation process consists of tandem C–S C–N bond formation by running under air atmosphere at ambient temperature. Broad substrate tolerance the sustainable protocol has verified practical synthesis divergent thiazoles with both monocyclic fused cyclic structures.

Язык: Английский

Процитировано

6