Oxidative organocatalytic chemoselective <i>N</i>-acylation of heterocycles with aromatic and conjugated aldehydes

Ta, Linda; Sundén, Henrik

doi:10.1039/c7cc08672e

Cited by 27 publications

(28 citation statements)

References 56 publications

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“…In this reaction, 6amino-1H-indazole (45 a) was treated with an aldehyde (45 b) in presence of carbene X1, Kharasch oxidant X2 and base DBU in DCM at room temperature to prepare desired N-1 acylated indazole (45 c) with 69% of yield (Scheme 45). [109] Vannucci and his group established an electrochemical synthetic procedure for selective N-1 acylation of 1H-indazole (46 a). The in situ anionic indazole was prepared first with the help of anion pool approach and then it was treated with acid anhydride which resulted in N-1 acylated indazole (46 b) (Scheme 46).…”

Section: Acylationmentioning

confidence: 99%

Direct Catalytic Functionalization of Indazole Derivatives

2020

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Indazoles are a very important class of N‐containing heterocycles with a wide range of biological and medicinal properties. The presence of different functionalities on indazole moieties enhances its biological activities. Hence, the preparation of indazole compounds bearing functional groups has gained a significant interest to the organic synthetic chemists. A large effort has been made to develop efficient and new methods for the functionalization of indazoles. Direct catalytic functionalization is a very powerful tool for facile synthesis of important indazole derivatives due to its straightforwardness. This review summarizes developments on direct functionalizations of indazoles published in the last two decades.

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Section: Acylationmentioning

confidence: 99%

Direct Catalytic Functionalization of Indazole Derivatives

2020

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“…Formation of this intermediate is usually carried out via the reaction of NHCs with α,β-unsaturated enol esters or ethers [ 84 , 85 , 86 ], ynals [ 87 , 88 , 89 , 90 ], 2-bromoenals [ 91 , 92 , 93 , 94 ], or acyl fluorides [ 95 , 96 ]. Moreover, formation α,β-unsaturated acylazolium is possible via two-electron oxidation of Breslow intermediate [ 97 , 98 , 99 , 100 , 101 , 102 , 103 ].…”

Section: Coates–claisen and Ireland–coates–claisen Rearrangementsmentioning

confidence: 99%

Organocatalytic Name Reactions Enabled by NHCs

et al. 2020

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Giving reactions the names of their discoverers is an extraordinary tradition of organic chemistry. Nowadays, this phenomenon is much rarer, although already named historical reactions are still often developed. This is also true in the case of a broad branch of N‑heterocyclic carbenes catalysis. NHCs allow many unique synthetic paths, including commonly known name reactions. This article aims to gather this extensive knowledge and compare historical reactions with current developed processes. Furthermore, this review is a great opportunity to highlight some of the unique applications of these procedures in the total synthesis of biologically active compounds. Hence, this concise article may also be a source of knowledge for scientists just starting their adventure with N‑heterocyclic carbene chemistry.

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“…More recently, Ta and Sunden developed a clever and chemoselective NHC‐catalyzed oxidative amidation strategy for the synthesis of N ‐acylated indoles ( 37 ) under mild conditions (Scheme a) . This method provided synthetically valuable acyl indoles in good‐to‐excellent yields with broad substrate scope.…”

Section: Synthesis Of Amides From Aldehydesmentioning

confidence: 99%

Carbonyl Compounds′ Journey to Amide Bond Formation

Reddy

Beatriz

Lima

2019

Chemistry An Asian Journal

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The formation of amide bonds is one of the most stimulating emerging areas in organic and medicinal chemistry.A mides are recognized as central building blocks in a plethora of interesting pharmaceuticals, proteins, peptides, polymers, naturalp roducts, functional materials, andb iologically relevant carbocyclic or heterocyclic molecules, and they are also found in av ariety of industrial fields. Therefore, a review of recent developments and challenges in the formation of amide bonds from carbonyl compounds is particular-ly important. Herein, we have scrutinized ar ange of metalcatalyzed andm etal-free approaches for the synthesis of amides from aldehydes, ketones, and oximes. In addition, this Minireview highlightsr elevant mechanistic studies, as well as the potential applications of these methods in the synthesis of candidate drug molecules. We hope that the data compiled herein will encourage further progress in this notable area of chemistry research.

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Oxidative organocatalytic chemoselective N-acylation of heterocycles with aromatic and conjugated aldehydes

Cited by 27 publications

References 56 publications

Direct Catalytic Functionalization of Indazole Derivatives

Direct Catalytic Functionalization of Indazole Derivatives

Organocatalytic Name Reactions Enabled by NHCs

Carbonyl Compounds′ Journey to Amide Bond Formation

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