Regioselective [3+2]‐Spiroannulation and [4+n]‐Annulation Approaches through Activation of C−H Bond Facilitated by Ru(II) as Catalyst: Role of Solvent Selectivity DOI
Rahul Dev Mandal, Anindita Sarkar, Dwaipayan Das

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(8), С. 1863 - 1876

Опубликована: Фев. 21, 2024

Abstract Ru(II)‐catalyzed and solvent‐switched [3+2]‐spiroannulation [4+n] (n=1, 2, 3) annulations of 2‐aryl quinazolinone or 2‐aryl‐2,3‐dihydrophthalazine‐1,4‐diones with ynones alkynyl alcohol 1,3‐diynes under mild reaction conditions have been analyzed. These reactions take place in the presence appropriate solvent features a redox‐neutral pathway. Ynone serves as an ‘atypical one‐carbon unit’ [4+1] annulation generates tetrasubstituted carbon center bearing diverse heterocycles through [3+2] strategies. Post transformations synthesized spiro‐products augments potential developed methodology.

Язык: Английский

Photoredox streamlines electrocatalysis: photoelectrosynthesis of polycyclic pyrimidin-4-ones through carbocyclization of unactivated alkenes with malonates DOI

Minglin Tao,

Feng Qin,

Kaixing Gong

и другие.

Green Chemistry, Год журнала: 2024, Номер 26(7), С. 4199 - 4208

Опубликована: Янв. 1, 2024

A new photoelectrocatalytic mode permits the synthesis of polycyclic pyrimidin-4-ones through dehydrogenative cyclization malonates with unactivated alkenes.

Язык: Английский

Процитировано

15

Synthesis of Substituted 1‐Hydroxy‐2‐Naphthaldehydes by Rhodium‐Catalyzed C−H Bond Activation and Vinylene Transfer of Enaminones with Vinylene Carbonate DOI
Min Liu, Kelu Yan, Jiangwei Wen

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2021, Номер 364(3), С. 512 - 517

Опубликована: Ноя. 30, 2021

Abstract The rhodium(III)‐catalyzed C−H bond activation and vinylene transfer of enaminones with carbonate have been proposed for the synthesis substituted 1‐hydroxy‐2‐naphthaldehydes in 49–84% yields. Several preliminary mechanistic studies hydroxyl‐directed derivatization reactions were also performed. This method offers an alternative approach 1‐hydroxy‐2‐naphthaldehydes. magnified image

Язык: Английский

Процитировано

48

Rhodium-Catalyzed Dehydrogenative Annulation of N-Arylmethanimines with Vinylene Carbonate for Synthesizing Quinolines DOI
Yan Hu, Jiang Nan,

Jiacheng Yin

и другие.

Organic Letters, Год журнала: 2021, Номер 23(21), С. 8527 - 8532

Опубликована: Окт. 20, 2021

Here we report a novel Rh-catalyzed C−H/C−H alkenylation of N-arylmethanimines with vinylene carbonate acting as unit. Forty examples C3,C4-nonsubstituted quinolines were achieved from commercially available starting materials. This identified process features an exceedingly simple system, lower loading catalyst, and the capacity for postfunctionalization bioactive molecules.

Язык: Английский

Процитировано

46

Recent advances in the synthesis of 2,3-fused quinazolinones DOI

Wang Wang,

Pei‐Sen Zou,

Li Pang

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(32), С. 6293 - 6313

Опубликована: Янв. 1, 2022

As one of the most important structural units in pharmaceuticals and medicinal chemistry, quinazolinone its derivatives exhibit a wide range biological pharmacological activities, including anti-inflammatory, antitubercular, antiviral, anticancer etc. In particular, 2,3-fused quinazolinones have attracted much attention because rings fused to 2,3-positions improve their rigidity planarity. Their synthetic strategies made great advances recent years. Therefore, this review focuses on novel for synthesis from 2017 2022, such as difunctionalization alkenes, ring-opening easily available small rings, dehydrogenative cross-coupling reactions, transition-metal catalyzed cyclizations, cycloadditions, other cascade reactions.

Язык: Английский

Процитировано

33

Synthesis of (2H)-Indazoles and Dihydrocinnolinones through Annulation of Azobenzenes with Vinylene Carbonate under Rh(III) Catalysis DOI
Min Seo Park,

Kyeongwon Moon,

Harin Oh

и другие.

Organic Letters, Год журнала: 2021, Номер 23(14), С. 5518 - 5522

Опубликована: Июль 6, 2021

The Rh(III)-catalyzed C–H functionalization and subsequent intramolecular cyclization between azobenzenes vinylene carbonate is described herein. Depending on the electronic property of azobenzenes, this transformation results in formation (2H)-indazoles or dihydrocinnolin-4-ones through generation ortho-alkylated azo-intermediates followed by decarboxylation. Surprisingly, acts as an acetaldehyde acetyl surrogate to enable [4 + 1] 2] annulation reaction. This characterized its mild reaction conditions, simplicity, excellent functional group compatibility.

Язык: Английский

Процитировано

39

Rhodium-catalysed direct formylmethylation using vinylene carbonate and sequential dehydrogenative esterification DOI

Moena Kato,

Koushik Ghosh, Yuji Nishii

и другие.

Chemical Communications, Год журнала: 2021, Номер 57(67), С. 8280 - 8283

Опубликована: Янв. 1, 2021

A rhodium-catalysed direct formylmethylation adopting vinylene carbonate as an ethynol equivalent is reported.

Язык: Английский

Процитировано

37

Synthesis of aminoisoquinolines via Rh-catalyzed [4 + 2] annulation of benzamidamides with vinylene carbonate DOI
Xin Huang, Yingying Xu,

Jianglian Li

и другие.

Chinese Chemical Letters, Год журнала: 2021, Номер 32(11), С. 3518 - 3521

Опубликована: Май 7, 2021

Язык: Английский

Процитировано

36

Manganese-Catalyzed [4 + 2] Annulation of N–H Amidines with Vinylene Carbonate via C–H Activation DOI
Yudong Li, Huan Wang, Ying Li

и другие.

The Journal of Organic Chemistry, Год журнала: 2021, Номер 86(24), С. 18204 - 18210

Опубликована: Ноя. 25, 2021

Manganese-catalyzed C-H bond functionalization of aryl amidines for the synthesis 1-aminoisoquinolines in presence vinylene carbonate has been developed. The reaction features a broad substrate scope and proceeds under mild conditions with only anion as byproduct.

Язык: Английский

Процитировано

34

Rh(III)-Catalyzed Synthesis of Indazolo[2,3-a]quinolines: Vinylene Carbonate as C1 and C2 Building Blocks DOI
Wei Hu, Chao Pi, Di Hu

и другие.

Organic Letters, Год журнала: 2022, Номер 24(14), С. 2613 - 2618

Опубликована: Апрель 4, 2022

A rhodium-catalyzed cyclization of azobenzenes and vinylene carbonate via C-H bond activation to construct indazolo[2,3-a]quinolines has been developed. This protocol offers an efficient method for synthesis the titled products in good yields with broad functional group tolerance. In this reaction, three C-C bonds C-N are formed one pot, (VC) acts as C1 C2 synthons well "vinylene transfer" agent acylation reagent construction target-fused heterocycles. Moreover, exhibit favorable fluorescence properties, which indicate their potential application fluorescent materials biosensors.

Язык: Английский

Процитировано

28

Ruthenium-catalyzed oxidative coupling of vinylene carbonate with isoxazoles: access to fused anthranils DOI
Pravin Kumar, Manmohan Kapur

Chemical Communications, Год журнала: 2022, Номер 58(28), С. 4476 - 4479

Опубликована: Янв. 1, 2022

A ruthenium-catalyzed oxidative coupling of vinylene carbonate with isoxazoles has been developed to achieve the direct C-H formylmethylation a diverse array arylisoxazoles utilizing isoxazole ring as directing group. simple manipulation established reaction conditions leads formation fused-anthranils. Importantly, functions both formylmethyl cation equivalent through decarboxylation process and an acetylene equivalent. Control experiments were conducted elucidate plausible mechanism. This methodology is expected provide facile expeditious approach for synthesis

Язык: Английский

Процитировано

25