4.5 Article

Catalyst-Free [3+2] Cycloaddition of Isoquinolinium/Pyridinium Ylides and Electron-Deficient Alkenes

相关参考文献

注意:仅列出部分参考文献,下载原文获取全部文献信息。
Article Chemistry, Organic

[3+2] cycloaddition for the assembly of indolizine-based heterocyclic sulfonyl fluorides

Huan Xiong et al.

Summary: This article presents a method for the construction of indolizine-based heterocyclic sulfonyl fluorides through [3 + 2] cycloaddition reaction. The method features mild conditions, high efficiency, easily obtained starting materials, and a broad substrate scope, which holds great potential value in medicinal chemistry and other related disciplines.

ORGANIC CHEMISTRY FRONTIERS (2023)

Article Chemistry, Organic

Highly Enantioselective Synthesis of [1,2,4]Triazino[5,4-a]isoquinoline Derivatives via (3+3) Cycloaddition Reactions of Diazo Compounds and Isoquinolinium Methylides

Wei Wu et al.

Summary: An array of chiral [1,2,4]triazino[5,4-a]isoquinoline derivatives were synthesized in excellent yields and enantioselectivities through a new highly asymmetric (3 + 3) cycloaddition reaction. The reaction was facilitated by a bifunctional chiral phasetransfer catalyst and density functional theory calculations revealed the catalyst's role in the deprotonation/protonation process. The obtained products were transformed into densely functionalized polycyclic heterocompounds with multiple stereocenters.

ORGANIC LETTERS (2022)

Article Chemistry, Organic

Cu-Catalyzed Oxidative [3+2] Annulation of 2-(Pyridine-2-yl)acetates with Maleimides: Synthesis of 1H-Pyrrolo[3,4-b]indolizine-1,3-diones

Kai-Hong Lv et al.

Summary: A novel protocol for the synthesis of highly functionalized indolizine derivatives, known as 1H-pyrrolo[3,4-b]-indolizine-1,3-diones (PIZDOs), has been developed through regioselective oxidative [3 + 2] annulation. The cascade oxidative reaction was achieved by heating a mixture of 2-(pyridine-2-yl)acetates and maleimides in the presence of Ag2CO3 and Cu(OAc)center dot H2O catalyst in chlorobenzene. The method allows for the one-pot oxidative annulation reaction to synthesize functionalized PIZDOs instead of multiple steps reactions, making it suitable for both combinatorial and parallel syntheses of PIZDOs.

JOURNAL OF ORGANIC CHEMISTRY (2022)

Article Chemistry, Multidisciplinary

Acid-Promoted Redox-Annulation toward 1,2-Disubstituted-5,6-dihydropyrrolo[2,1-α]isoquinolines: Synthesis of the Lamellarin Core

Guo-Quan Hou et al.

Summary: An efficient synthesis method for a variety of 1,2-disubstituted-5,6-dihydropyrrolo[2,1-alpha]isoquinoline derivatives has been reported. This method involves an acid promoted cyclization reaction between 1,2,3,4-tetrahydroisoquinoline (THIQ) and substituted alpha,beta-unsaturated aldehyde derivatives. The reaction yields structurally diverse multisubstituted dihydropyrrolo[2,1-alpha]isoquinolines in moderate to good yields, which serve as the core scaffold of the marine natural alkaloid lamellarins.

ACS OMEGA (2022)

Article Chemistry, Organic

Transition metal-free annulative vinylene transfer via the 1,3-dipolar reaction of N-ylides: access to benzo-fused indolizines

Limin Zhao et al.

Summary: An efficient metal-free protocol for the synthesis of benzo-fused indolizines has been developed using 1,3-dipolar cycloadditions of N-ylides with vinylene carbonate. Vinylene carbonate serves as an acetylene surrogate without the need for an external oxidant. This transformation allows for the direct construction of versatile benzo-fused indolizine derivatives in moderate to good yields.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

Article Chemistry, Organic

Tungsten catalysed decarboxylative [3+2] cycloaddition aromatization: one-pot synthesis of trifluoromethyl-pyrrolo[2,1-a]isoquinolines with visible light irradiation

Daohong Yu et al.

Summary: A synthetic method for constructing trifluoromethyl-pyrrolo[2,1-a]isoquinolines via decarboxylation and photocatalytic reactions is described. This method exhibits broad substrate compatibility and enables facile access to pharmaceutically active derivatives.

ORGANIC CHEMISTRY FRONTIERS (2022)

Article Chemistry, Multidisciplinary

Asymmetric Catalytic Synthesis of Hexahydropyrrolo-isoquinolines via Three-Component 1,3-Dipolar-Cycloaddition

Zhaojing Li et al.

Summary: An asymmetric three-component 1,3-dipolar cycloaddition has been achieved using a chiral catalyst, resulting in a series of hexahydropyrrolo-isoquinolines with excellent diastereo- and enantioselectivities.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

Article Chemistry, Organic

Iron Catalyzed [3+2] Cycloaddition of Tetrahydroisoquinoline: Synthesis of Dihydropyrrolo[2,1-a]isoquinolines

Si-Wei Liu et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2020)

Review Chemistry, Organic

[3+2]-Cycloaddition of Catalytically Generated Pyridinium Ylide: A General Access to Indolizine Derivatives

Shanliang Dong et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2020)

Review Chemistry, Organic

New applications of pyridinium ylides toward heterocyclic synthesis

Liya D. Funt et al.

TETRAHEDRON (2020)

Article Chemistry, Multidisciplinary

Diversified Transformations of Tetrahydroindolizines to Construct Chiral 3-Arylindolizines and Dicarbofunctionalized 1,5-Diketones

Dong Zhang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Organic

Synthesis of Indolizines from Pyridinium Salts and Ethyl Bromodifluoroacetate

Xiaoya Hou et al.

ORGANIC LETTERS (2020)

Article Chemistry, Applied

Direct Synthesis of Dihydropyrrolo[2,1-a]Isoquinolines through FeCl3 Promoted Oxidative Aromatization

Hai-Lei Cui et al.

ADVANCED SYNTHESIS & CATALYSIS (2019)

Article Chemistry, Organic

Diastereoselective Synthesis of Polycyclic Indolizines with 2-(2-Enynyl)pyridines and Enamines

Stalin R. Pathipati et al.

ORGANIC LETTERS (2018)

Article Chemistry, Multidisciplinary

Asymmetric Synthesis of Tetrahydroindolizines by Bimetallic Relay Catalyzed Cycloaddition of Pyridinium Ylides

Dong Zhang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Review Biochemistry & Molecular Biology

Pyrrolizidine alkaloids: occurrence, biology, and chemical synthesis

Jeremy Robertson et al.

NATURAL PRODUCT REPORTS (2017)

Article Chemistry, Organic

Iron-Catalyzed Indolizine Synthesis from Pyridines, Diazo Compounds, and Alkynes

Tim Douglas et al.

ORGANIC LETTERS (2017)

Article Chemistry, Organic

A [3+2] - [4+2] - [3+2] cycloaddition sequence of isoquinolinium ylide

Ruzhang Liu et al.

ORGANIC CHEMISTRY FRONTIERS (2017)

Article Chemistry, Multidisciplinary

Catalytic Asymmetric [3+1]-Cycloaddition Reaction of Ylides with Electrophilic Metallo-enolcarbene Intermediates

Yongming Deng et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Review Chemistry, Multidisciplinary

The cycloaddition reaction using visible light photoredox catalysis

Yu Liu et al.

SCIENCE CHINA-CHEMISTRY (2016)

Article Chemistry, Multidisciplinary

Stereoselective Synthesis of Tetrahydroindolizines through the Catalytic Formation of Pyridinium Ylides from Diazo Compounds

Jonathan Day et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

N-Heterocyclic carbene-catalyzed [2+3] cyclocondensation of α-chloroaldehydes with azomethine imines

Zhong-Hua Gao et al.

CHEMICAL COMMUNICATIONS (2015)

Article Chemistry, Multidisciplinary

Phosphine-catalyzed dearomatizing [3+2] annulations of isoquinolinium methylides with allenes

Zhi-Jun Jia et al.

CHEMICAL COMMUNICATIONS (2015)

Article Chemistry, Organic

Synthesis of lndolizine Derivatives by Pd-Catalyzed Oxidative Carbonylation

Tongyu Xu et al.

ORGANIC LETTERS (2015)

Article Chemistry, Organic

Synthesis of Lepadiformine Using a Hydroamination Transform

M. Greg Tabor et al.

ORGANIC LETTERS (2015)

Article Chemistry, Organic

Electrophilicities of 1,2-Disubstituted Ethylenes

Dominik S. Allgaeuer et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2014)

Article Chemistry, Multidisciplinary

Nucleophilicity Parameters of Pyridinium Ylides and Their Use in Mechanistic Analyses

Dominik S. Allgaeuer et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

Article Chemistry, Organic

A Modular Synthesis of Polysubstituted Indolizines

Murat Kucukdisli et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2012)

Review Chemistry, Organic

REACTIONS OF PYRIDINIUM N-YLIDES AND THEIR RELATED PYRIDINIUM SALTS

Akikazu Kakehi

HETEROCYCLES (2012)

Article Chemistry, Multidisciplinary

Enantioselective Michael/Cyclization Reaction Sequence: Scaffold-Inspired Synthesis of Spirooxindoles with Multiple Stereocenters

Yiming Cao et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

Article Chemistry, Multidisciplinary

Organocatalytic enantioselective (3+2) cycloaddition using stable azomethine ylides

Naiara Fernandez et al.

CHEMICAL COMMUNICATIONS (2011)

Article Chemistry, Multidisciplinary

Visible light mediated azomethine ylide formation-photoredox catalyzed [3+2] cycloadditions

Magnus Rueping et al.

CHEMICAL COMMUNICATIONS (2011)

Article Chemistry, Organic

Pyridinium Ylids in Heterocyclic Synthesis

Jan Jacobs et al.

CURRENT ORGANIC CHEMISTRY (2011)

Article Chemistry, Multidisciplinary

Pyridine Activation via Copper(I)-Catalyzed Annulation toward indolizines

Jose Barluenga et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

Review Biochemistry & Molecular Biology

Indolizidine and quinolizidine alkaloids

Joseph P. Michael

NATURAL PRODUCT REPORTS (2008)

Review Biochemistry & Molecular Biology

Indolizidine and quinolizidine alkaloids

Joseph P. Michael

NATURAL PRODUCT REPORTS (2007)

Article Chemistry, Organic

Asymmetric synthesis of enantioenriched (+)-elaeokanine A

R. Karl Dieter et al.

JOURNAL OF ORGANIC CHEMISTRY (2006)

Review Plant Sciences

Alkaloids from amphibian skin: A tabulation of over eight-hundred compounds

JW Daly et al.

JOURNAL OF NATURAL PRODUCTS (2005)

Article Chemistry, Organic

Novel bioactive isoquinoline alkaloids from Carduus crispus

QY Zhang et al.

TETRAHEDRON (2002)