Nickel‐Catalyzed Annulation of o‐Haloarylamidines with Aryl Acetylenes: Synthesis of Isoquinolone and 1‐Aminoisoquinoline Derivatives DOI
Hao Xie,

Qiaoyan Xing,

Zhifei Shan

et al.

Advanced Synthesis & Catalysis, Journal Year: 2019, Volume and Issue: 361(8), P. 1896 - 1901

Published: Feb. 11, 2019

Abstract An efficient method for the synthesis of substituted 1(2 H )‐isoquinolone derivatives via nickel‐catalyzed annulation 2‐halobenzamidines with aryl alkynes in presence water is described. Benzo[4,5]imidazo[2,1‐ a ]isoquinolines were formed as dominated products when dry dimethyl sulfoxide was used solvent. Furthermore, benzyl amidines substrates, debenzylation reaction occured to provide various 1‐aminoisoquinoline products. magnified image

Language: Английский

Recent advances in the synthesis of carbazoles from indoles DOI

Trapti Aggarwal,

Sushmita Sushmita,

Akhilesh K. Verma

et al.

Organic & Biomolecular Chemistry, Journal Year: 2019, Volume and Issue: 17(36), P. 8330 - 8342

Published: Jan. 1, 2019

Synthesis of carbazoles using indoles as precursors through CH activation/annulation.

Language: Английский

Citations

80

Aerobic Oxidative Functionalization of Indoles DOI

Saiwen Liu,

Feng Zhao, Xing Chen

et al.

Advanced Synthesis & Catalysis, Journal Year: 2020, Volume and Issue: 362(18), P. 3795 - 3823

Published: May 18, 2020

Abstract The synthetic methodology for direct indole functionalizations is of great significance in chemistry and has been intensively investigated the last few decades. From perspective green chemistry, oxygen best choice as terminal oxidant molecular synthesis. Hence, aerobic oxidative functionalization indoles became a hot research topic decade. Numerous efficient protocols this field have discovered that enable facile transformations to related valuable compounds, which are summarized discussed detail review. magnified image

Language: Английский

Citations

72

Benzannulation strategies for the synthesis of carbazoles, indolocarbazoles, benzocarbazoles, and carbolines DOI
Ankush Banerjee,

Samrat Kundu,

Arya Bhattacharyya

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(11), P. 2710 - 2771

Published: Jan. 1, 2021

This review presents a critical and authoritative analysis of several exciting benzannulation approaches developed in the past decade for construction carbazoles, indolocarbazoles, benzocarbazoles, carbolines.

Language: Английский

Citations

71

Three-component synthesis of 2-heteroaryl-benzothiazoles under metal-free conditions DOI
Guozheng Li, Hao Xie, Jinjin Chen

et al.

Green Chemistry, Journal Year: 2017, Volume and Issue: 19(17), P. 4043 - 4047

Published: Jan. 1, 2017

2-Heteroaryl-benzothiazole derivatives were selectively prepared from anilines, 2-methylquinolines and elemental sulfur under metal-free conditions.

Language: Английский

Citations

80

Bismuth(III) Triflate Catalyzed Three-Component Reactions of Indoles, Ketones, and α-Bromoacetaldehyde Acetals Enable Indole-to-Carbazole Transformation DOI
Yanlong Gu, Wenbo Huang, Shaomin Chen

et al.

Organic Letters, Journal Year: 2018, Volume and Issue: 20(14), P. 4285 - 4289

Published: July 6, 2018

A three-component reaction of indoles, α-bromoacetaldehyde acetals, and ketones was developed by using bismuth(III) triflate as the catalyst to realize a straightforward approach for synthesizing carbazole derivatives. The established mechanistically through autotandem catalysis Bi(OTf)3 in following two steps: (i) Friedel–Crafts-type alkylation indole with acetal, which produced tryptaldehyde-type intermediate (ii) [4 + 2] annulation this ketone component.

Language: Английский

Citations

58

Three‐Component Thieno[2,3‐b]indole Synthesis from Indoles, Alkenes or Alkynes and Sulfur Powder under Metal‐Free Conditions DOI
Bin Li, Penghui Ni, Huawen Huang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2017, Volume and Issue: 359(24), P. 4300 - 4304

Published: Oct. 3, 2017

Abstract A Bronsted acid promoted three‐component synthesis of substituted thieno[2,3‐ b ]indole has been developed starting from indoles, alkenes or alkynes, and sulfur powder. N , ‐Dimethylformamide plays an important role to convert the materials into fused products. Various functional groups attached substrates were well tolerated afford corresponding products in moderate good yields under very simple reaction conditions. magnified image

Language: Английский

Citations

55

Benzannulation of 2‐Alkenylindoles using Aldehydes by Sequential Triple‐Relay Catalysis: A Route to Carbazoles and Carbazole Alkaloids DOI
Ankush Banerjee, Samrat Sahu, Modhu Sudan Maji

et al.

Advanced Synthesis & Catalysis, Journal Year: 2017, Volume and Issue: 359(11), P. 1860 - 1866

Published: April 13, 2017

Abstract Benzannulation of 2‐alkenylindoles with readily available aldehydes, under one‐pot sequential triple‐relay‐catalysis, provides an easy access to several structurally unique carbazoles including 2‐ and 3‐alkenylcarbazoles. This protecting group‐free method enabled synthesis alkaloids such as hyellazole 6‐chlorohyellazole, the formal syntheses seven other alkaloids. Construction core structure, present in murastifoline A, murrafoline E, related was also demonstrated. Even conjugated 3,3′‐biscarbazoles can be synthesized by one‐pot, two‐fold triple‐relay catalysis . magnified image

Language: Английский

Citations

54

Diastereoselective construction of carbazole-based spirooxindoles via the Levy three-component reaction DOI

Shao‐Cong Zhan,

Jing Sun,

Ruzhang Liu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2019, Volume and Issue: 18(1), P. 163 - 168

Published: Dec. 2, 2019

The CuSO4 catalyzed three-component reaction of indole-2-acetate, aromatic aldehydes and 3-methyleneoxindoles in toluene at 130 °C afforded polysubstituted spiro[carbazole-3,3'-indolines] good yields with high diastereoselectivity. When isatylidene malononitriles were used as dienophiles, regio-isomeric spiro[carbazole-2,3'-indolines] selectively obtained. A similar 2-arylidene-1,3-indanediones resulted spiro[carbazole-3,2'-indenes] satisfactory stereochemistry the diastereoisomers spiro compounds was clearly elucidated by analysis NMR spectra determination fourteen single crystal structures. mechanism included formation reactive 2,3-dimethyleneindoline a sequential Diels-Alder reaction.

Language: Английский

Citations

49

A Three-Component Strategy for Benzoselenophene Synthesis under Metal-Free Conditions Using Selenium Powder DOI
Penghui Ni, Jing Tan, Wenqi Zhao

et al.

Organic Letters, Journal Year: 2019, Volume and Issue: 21(10), P. 3518 - 3522

Published: May 6, 2019

An efficient three-component benzoselenophenes formation has been developed from substituted indoles, acetophenones, and selenium powder under metal-free conditions. 2-Aryl indoles played an important role to promote benzoselenophene acetophenone derivatives powder. One C–C two C–Se bonds were selectively formed provide 40 new in good yields.

Language: Английский

Citations

43

Recent advances in the transition metal-free oxidative dehydrogenative aromatization of cyclohexanones DOI

Kun Deng,

Huawen Huang, Guo‐Jun Deng

et al.

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(29), P. 6380 - 6391

Published: Jan. 1, 2021

Cyclohexanone is a simple and widely available raw material that can be obtained from lignin biomass, highlighting its renewable sustainable features. Cyclohexanone, as an important synthon in organic chemistry, has been demonstrated to viable for constructing functionalized arenes benzoheteroarenes, with recent extensive development on transition metal-free oxidative dehydrogenative aromatization. This review focuses research progress the derivation of cyclohexanones via

Language: Английский

Citations

33