Carbodiimide-based synthesis of N-heterocycles: moving from two classical reactive sites to chemical bond breaking/forming reaction

Wang, Yang; Zhang, Wen‐Xiong; Xi, Zhenfeng

doi:10.1039/c9cs00478e

Cited by 101 publications

(61 citation statements)

References 352 publications

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“…2,8,19 However, many of these methods need the use of expensive catalysts and toxic reagents. 20,21 In addition, direct functionalization of the heterocyclic rings for synthesis of compounds derived from quinoline is relatively less common as it often requires harsh reaction conditions and suffers from poor selectivity.…”

Section: Introductionmentioning

confidence: 99%

Enzymatic approaches to site-selective oxidation of quinoline and derivatives

et al. 2022

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Section: Introductionmentioning

confidence: 99%

Enzymatic approaches to site-selective oxidation of quinoline and derivatives

et al. 2022

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“…[3] Theclassical synthetic methods for their preparation usually suffer from specific reaction conditions, toxic reagents,a nd especially generation of (over)stoichiometric amounts of waste. [4] To overcome these problems, alcohols have been introduced as starting materials for the synthesis of N-heterocycles since many of them can be easily obtained from abundant biomass. [5] Thef irst report in this area applying heterogeneous materials dates back to 1982, when Mares and co-workers discovered that alcohols can be converted to aldehydes by Mo/Rh bimetallic catalysts producing only hydrogen as byproduct.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of N‐Heterocycles via Oxidant‐Free Dehydrocyclization of Alcohols Using Heterogeneous Catalysts

Sun

Shan

et al. 2021

Angew Chem Int Ed

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N‐Heterocycles, such as pyrroles, pyrimidines, quinazolines, and quinoxalines, are important building blocks for organic chemistry and the fine‐chemical industry. For their synthesis, catalytic borrowing hydrogen and acceptorless dehydrogenative coupling reactions of alcohols as sustainable reagents have received significant attention in recent years. To overcome the problems of product separation and catalyst reusability, several metal‐based heterogeneous catalysts have been reported to achieve these transformations with good yields and selectivity. In this Minireview, we summarize recent developments using both noble and non‐noble metal‐based heterogeneous catalysts to synthesize N‐heterocycles from alcohols and N‐nucleophiles via acceptorless dehydrogenation or borrowing hydrogen methodologies. Furthermore, this Minireview introduces strategies for the preparation and functionalization of the corresponding heterogeneous catalysts, discusses the reaction mechanisms and the roles of metal electronic states, and the influence of support Lewis acid–base properties on these reactions.

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“…Deep attention to the fundamental role of organic building blocks based on carbon–nitrogen (C–N) bonding in pharmaceutical and industrial fields justifies the demand for the synthesis of these compounds. [ 1–3 ] Nowadays, extensive research is carried out to provide these structures in affordable conditions. Most of these building blocks are vital compounds found in structures of the human body, such as pyrimidines in DNA structures or amino acids in proteins.…”

Section: Introductionmentioning

confidence: 99%

Carbon–nitrogen bond formation using modified graphene oxide derivatives decorated with copper complexes and nanoparticles

Mirza‐Aghayan

Saeedi

Boukherroub

2021

Applied Organom Chemis

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Several catalytic reactions such as Ullmann, Chan–Lam, Huisgen 1,3‐dipolar cycloaddition, [2 + 3] cycloaddition, condensation, and coupling reactions under suitable conditions have been used for the synthesis of fundamental structures containing a carbon–nitrogen (C–N) bond. Graphene oxide (GO) and its derivatives as heterogeneous catalysts have attracted considerable attention for the synthesis of organic building blocks. Loading of GO derivatives with copper complexes or nanoparticles, as one of the most abundant and low toxic transition metals, allowed to design new composites with predominant ability to C–N bond formation. In this review article, we present a comprehensive overview on the synthesis of building blocks containing a C–N bond such as amines, triazoles, tetrazoles, propargyl amines, imidazoles, and benzodiazepines using GO derivatives loaded with copper complexes or nanoparticles.

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Carbodiimide-based synthesis of N-heterocycles: moving from two classical reactive sites to chemical bond breaking/forming reaction

Abstract: The extensive synthetic application of carbodiimides in various types of N-heterocyclic systems from the 1980s to today is outlined.

Cited by 101 publications

References 352 publications

Enzymatic approaches to site-selective oxidation of quinoline and derivatives

Enzymatic approaches to site-selective oxidation of quinoline and derivatives

Synthesis of N‐Heterocycles via Oxidant‐Free Dehydrocyclization of Alcohols Using Heterogeneous Catalysts

Carbon–nitrogen bond formation using modified graphene oxide derivatives decorated with copper complexes and nanoparticles

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