4.8 Article

Synthesis of Indole-Fused Oxepines via C-H Activation Initiated Diastereoselective [5+2] Annulation of Indoles with 1,6-Enynes

Related references

Note: Only part of the references are listed.
Review Chemistry, Multidisciplinary

Transition Metal-Catalyzed Intermolecular Cascade C-H Activation/Annulation Processes for the Synthesis of Polycycles

Liangliang Song et al.

Summary: Multiple strategies have been developed for the synthesis of polycycles, relying on transition metal-catalyzed C-H activation followed by intermolecular annulation reactions. These methods offer rapid, concise, and efficient construction of diverse polycycles.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

Article Chemistry, Organic

Rh(III)-Catalyzed [3+2] Annulation and C-H Alkenylation of Indoles with 1,3-Diynes by C-H Activation

Sanjeev Kumar et al.

Summary: The Rh(III)-catalyzed [3+2] annulations and C2-alkenylations of indoles with 1,3-diynes described in this study deliver synthetically important 3H-pyrrolo[1,2-a]indol-3-ones and highly functionalized tetrasubstituted olefin derivatives, with high efficiency and broad functional group compatibility. Additionally, the method has been successfully extended to the synthesis of bis-annulated and trisubstituted alkenes, as well as for the core structure synthesis of protein kinase C inhibitors and melatonin analogues.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Organic

Formal (3+4)-Annulation of Propargylic p-Quinone Methides with 2-Indolylmethanols: Synthesis of Polysubstituted Indole-Fused Oxepines

Zong-Wang Qiu et al.

Summary: A novel Bronsted acid catalyzed (3 + 4)-annulation method has been developed for the synthesis of polysubstituted indole-fused oxepines with high yields. This method explores the use of 2-indolylmethanols as four-atom synthons for the first time under Bronsted acid conditions.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Organic

Rh(III)-Catalyzed Divergent Synthesis of Alkynylated Imidazo[1,5-a]indoles and α,α-Difluoromethylene Tetrasubstituted Alkenes

Fei Zhao et al.

Summary: In this study, alkynylated imidazo[1,5-a]indoles and alpha,alpha-difluoromethylene tetrasubstituted alkenes were successfully synthesized via Rh(III)-catalyzed [4 + 1] annulation/alkyne moiety migration and C-H alkenylation/DG migration, showing excellent product selectivity, high yields, and good tolerance of functional groups.

ORGANIC LETTERS (2021)

Article Chemistry, Organic

Regioselective cascade annulation of indoles with alkynediones for construction of functionalized tetrahydrocarbazoles triggered by Cp*RhIII-catalyzed C-H activation

Jiaxu Tang et al.

Summary: This study presents an efficient regioselective and stereoselective cascade annulation of indoles with alkynediones via Cp*Rh-III-catalyzed indole C2-H activation using N-carboamide directing groups, providing valuable intermediates for the total synthesis of related indole alkaloids. The methodology offers a novel and straightforward approach to the synthesis of free (NH) tetrahydrocarbazoles and pyridoindolones with continuous quaternary carbons in good to excellent yields and wide substrate scope, demonstrating the C2 and C3 difunctionalization of indoles in one-pot.

ORGANIC CHEMISTRY FRONTIERS (2021)

Review Chemistry, Multidisciplinary

Total Synthesis of Natural Products with Bridged Bicyclo[m.n.1] Ring Systems via Type II [5+2] Cycloaddition

Long Min et al.

ACCOUNTS OF CHEMICAL RESEARCH (2020)

Article Chemistry, Organic

Metal-Catalyzed Regiospecific (4+3) Cyclization of 2-Indolylmethanols withortho-Quinone Methides

Si-Jia Zhou et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2020)

Article Chemistry, Multidisciplinary

Double annulation ofortho- andperi-C-H bonds of fused (hetero)arenes to unusual oxepino-pyridines

Majji Shankar et al.

CHEMICAL SCIENCE (2020)

Review Chemistry, Multidisciplinary

Synthetic applications of type II intramolecular cycloadditions

Long Min et al.

CHEMICAL SOCIETY REVIEWS (2020)

Article Chemistry, Multidisciplinary

Allylic Acetals as Acrolein Oxonium Precursors in Tandem C-H Allylation and [3+2] Dipolar Cycloaddition

Heeyoung Lee et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Catalytic Asymmetric (4+3) Cyclizations of In Situ Generated ortho-Quinone Methides with 2-Indolylmethanols

Meng Sun et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Re-Catalyzed Annulations of Weakly Coordinating N-Carbamoyl Indoles/Indolines with Alkynes via C-H/C-N Bond Cleavage

Yunhui Yang et al.

CHEMISTRY-A EUROPEAN JOURNAL (2019)

Article Chemistry, Multidisciplinary

Concise Synthesis of Polysubstituted Carbohelicenes by a C-H Activation/Radical Reaction/C-H Activation Sequence

Jiangliang Yin et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Review Chemistry, Multidisciplinary

A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry

Carlo Sambiagio et al.

CHEMICAL SOCIETY REVIEWS (2018)

Article Chemistry, Organic

Arylative Cyclization of Indole-1-carboxamides with 1,6-Enynes for the Synthesis of Polycyclic Indole Scaffolds

Chatrala Ravikumar Reddy et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2017)

Article Chemistry, Multidisciplinary

Stereoselective Synthesis of Tetrasubstituted Alkenes via a Cp*CoIII-Catalyzed C-H Alkenylation/Directing Group Migration Sequence

Hideya Ikemoto et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Review Chemistry, Organic

Transition metal-catalyzed C-H bond functionalizations by the use of diverse directing groups

Zhengkai Chen et al.

ORGANIC CHEMISTRY FRONTIERS (2015)

Article Chemistry, Multidisciplinary

Tunable Arylative Cyclization of 1,6-Enynes Triggered by Rhodium(III)-Catalyzed C-H Activation

Yuki Fukui et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Article Chemistry, Organic

Controlling bacterial behavior with indole-containing natural products and derivatives

Roberta J. Melander et al.

TETRAHEDRON (2014)

Review Chemistry, Multidisciplinary

Marine Indole Alkaloids: Potential New Drug Leads for the Control of Depression and Anxiety

Anna J. Kochanowska-Karamyan et al.

CHEMICAL REVIEWS (2010)

Review Chemistry, Multidisciplinary

Catalytic Functionalization of Indoles in a New Dimension

Marco Bandini et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

Article Biochemistry & Molecular Biology

Alstilobanines A-E, new indole alkaloids from Alstonia angustiloba

Koichiro Koyama et al.

BIOORGANIC & MEDICINAL CHEMISTRY (2008)

Article Chemistry, Multidisciplinary

Intra- and intermolecular reactions of indoles with alkynes catalyzed by gold

Catalina Ferrer et al.

CHEMISTRY-A EUROPEAN JOURNAL (2007)

Review Chemistry, Multidisciplinary

Convergent strategies for syntheses of trans-fused polycyclic ethers

M Inoue

CHEMICAL REVIEWS (2005)

Review Chemistry, Multidisciplinary

Synthesis and functionalization of Indoles through palladium-catalyzed reactions

S Cacchi et al.

CHEMICAL REVIEWS (2005)

Review Biochemistry & Molecular Biology

Simple indole alkaloids and those with a non-rearranged monoterpenoid unit

M Somei et al.

NATURAL PRODUCT REPORTS (2005)

Review Chemistry, Multidisciplinary

Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis

A Deiters et al.

CHEMICAL REVIEWS (2004)

Article Chemistry, Multidisciplinary

Angustilodine, an unusual pentacyclic indole alkaloid from Alstonia

TS Kam et al.

HELVETICA CHIMICA ACTA (2004)