Facile synthesis of dihydroisobenzofuran derivatives via a one-pot sequential Passerini-azide/Ag(I)-catalyzed cyclization process DOI

Yan Luo,

Haifeng Yu,

Yang Li-na

и другие.

Tetrahedron, Год журнала: 2024, Номер 158, С. 133984 - 133984

Опубликована: Апрель 13, 2024

Язык: Английский

Visible-light-induced cascade reaction: a sustainable approach towards molecular complexity DOI
Sumit Ghosh, Pranjal Pyne,

Anogh Ghosh

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(8), С. 1591 - 1628

Опубликована: Янв. 1, 2023

Photoredox catalysis has demonstrated rapid evolution in the field of synthetic organic chemistry. On other hand, splendour cascade reactions providing complex molecular architectures renders them a cutting-edge research area. Therefore, merging photocatalysis with synthesis brings out paradigm immense potential. The development photocascade for target molecule particular skeleton and stereochemical framework presents certain challenges but provides robust environmentally benign alternative. This comprehensive review assembles all accomplishments highlights visible-light-induced literature coverage up to October 2022.

Язык: Английский

Процитировано

30

Chemodivergent Synthesis of Benzofurans and 2,3‐Dihydrobenzofurans via Tandem Oxidative Annulation of Enaminones and Salicylaldehydes DOI
Xiyan Duan, Hui Li, Junqi Wang

и другие.

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(15), С. 1727 - 1733

Опубликована: Март 26, 2024

Comprehensive Summary Chemodivergent synthesis of benzofurans and 2,3‐dihydrobenzofurans has been realized. Under a reaction system consisting DBDMH K 2 CO 3 as promotors, controlled conditions enabled the formation two sets valuable heterocycles from tandem transformation enaminones salicylaldehydes. The key to success was identification parameters, in which imine intermediate formed by transient halogenation coupling substitution processes underwent either aldol condensation/annulation or hydrolysis/aldol condensation. additives NH 4 Cl Fe (SO ) unique selectivity this reaction. A broad substrate scope salicylaldehydes employed reaction, demonstrating excellent functional group tolerance versatility.

Язык: Английский

Процитировано

7

Development of novel transition metal-catalyzed synthetic approaches for the synthesis of a dihydrobenzofuran nucleus: a review DOI Creative Commons

Rabia Ashraf,

Ameer Fawad Zahoor, Kulsoom Ghulam Ali

и другие.

RSC Advances, Год журнала: 2024, Номер 14(21), С. 14539 - 14581

Опубликована: Янв. 1, 2024

The synthesis of dihydrobenzofuran scaffolds bears pivotal significance in the field medicinal chemistry and organic synthesis. These heterocyclic hold immense prospects owing to their significant pharmaceutical applications as they are extensively employed essential precursors for constructing complex frameworks. Their versatility importance make them an interesting subject study researchers scientific community. While exploring synthesis, have unveiled various novel efficient pathways assembling core. In wake extensive data being continuously reported each year, we outlined recent updates (post 2020) on methodological accomplishments employing catalytic role several transition metals forge functionalities.

Язык: Английский

Процитировано

6

A TBADT photocatalyst-enabled radical-induced cyclization pathway to access functionalized dihydrobenzofurans DOI

Punith S Gowda,

Duddu S. Sharada,

Gedu Satyanarayana

и другие.

Chemical Communications, Год журнала: 2023, Номер 59(59), С. 9094 - 9097

Опубликована: Янв. 1, 2023

Herein, this work describes a photoinduced visible light-mediated radical cyclization for constructing dihydrobenzofuran (DHB) scaffolds. Notably, cascade photochemical process is tolerable with various aromatic aldehydes and diverse alkynyl aryl ethers proceeds via an intramolecular 1,5-hydrogen atom transfer (HAT) pathway. Significantly, acyl C-H activation under mild conditions has been achieved without the use of additives or reagents. The photocatalyst, tetrabutylammonium decatungstate (TBADT), plays important role in present strategy by facilitating well-known hydrogen during course reaction.

Язык: Английский

Процитировано

11

Thiol-Triggered Tandem Dearomative Michael Addition/Intramolecular Henry Reaction of 2-Nitrobenzofurans: Access to Sulfur-Containing Polyheterocyclic Compounds DOI

Jun-Rui Zhuo,

Jian‐Qiang Zhao, Lei Yang

и другие.

Organic Letters, Год журнала: 2024, Номер 26(13), С. 2623 - 2628

Опубликована: Март 24, 2024

An efficient dearomative cyclization of 2-nitrobenzofurans via a thiol-triggered tandem Michael addition/intramolecular Henry reaction has been developed. A range thiochromeno[3,2-b]benzofuran-11-ols and tetrahydrothieno[3,2-b]benzofuran-3-ols could be obtained in up to 99% yield >20:1 dr. The valuable thiochromone fused benzofurans prepared with the 2-mercaptobenzaldehyde reaction/rearomatization/oxidative dehydrogenation process one-pot two-step operation. mechanism for was tentatively proposed.

Язык: Английский

Процитировано

4

DBU-catalyzed annulation strategy for modular assembly of 2,3-difunctionalized dihydrobenzofurans DOI

Lili Yuan,

Jie Wang, Qiang Tang

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

An organocatalytic approach for the construction of 2,3-dihydrobenzofuran scaffold through a formal [4 + 1] annulation 2-(2-nitrovinyl)phenols and α-bromoacetophenones in presence 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) has been developed. This protocol could be easily performed one mmol scale, giving broad range derivatives moderate to excellent yields remarkable diastereoselectivity (>20 : 1 dr general) with good functional group tolerance.

Язык: Английский

Процитировано

0

Chalcogen dihydrobenzofuran compounds as potential neuroprotective agents: an in vitro and in silico biological investigation DOI

Tácia Katiane Hall,

Larissa Sander Magalhães,

Mariana Parron Paim

и другие.

Biochimie, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Язык: Английский

Процитировано

0

The literature of heterocyclic chemistry, part XXII, 2022 DOI
Галина А. Газиева, Yu. B. Evdokimenkova, N. O. Soboleva

и другие.

Advances in heterocyclic chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Язык: Английский

Процитировано

0

Base‐Mediated [4+1] Annulation Strategy for Modular Assembly of Alkynyl/Carboxylated Dihydrobenzofurans DOI Open Access

Yangzilin Kong,

Yinsong Wu,

Yanan Liu

и другие.

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

Опубликована: Март 17, 2025

Abstract An efficient and operational [4+1] annulation strategy toward functional dihydrobenzofurans from 2‐bromomalonates in situ generated alkynyl o ‐quinone methides (from ‐hydroxyphenyl propargylamines) has been developed. Without the need for pre‐dried solvent inert atmosphere protection, a broad range of substituted propargylamines are well‐tolerated, producing expected alkynyl/carboxylated with good to high yields. Furthermore, gram‐scale synthesis valuable alkenyl/carboxylated construction were conducted provide great potential value medicinal chemistry other related disciplines.

Язык: Английский

Процитировано

0

Three-Component 1,3-Difunctionalization of Carbonyl Ylides with Water and Azadienes for the Synthesis of Dihydroisobenzofurans DOI
Haiqing Wang,

Yunzhe Wang,

Jie Ren

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 27, 2025

Multicomponent reactions are an efficient and widely employed synthetic strategy, known for their capability to rapidly effectively construct complex molecular architectures from multiple starting materials. This work presents a chemo- diastereoselective three-component reaction the 1,3-difunctionalization of transient carbonyl ylides with H2O azadienes, facilitated by synergistic catalysis Rh2(OAc)4 phosphoric acid. strategy provides protocol synthesis highly functionalized dihydroisobenzofurans in high yields (up 94%) good diastereoselectivities 91:9 dr). Additionally, subsequent transformations nucleophiles enable structurally diverse compounds enhanced (dr >95:5).

Язык: Английский

Процитировано

0