Synthesis of 10H‐indolo[1,2‐a]indole Derivatives via Intramolecular Cycloaddition and H‐Migration

2021 ◽  
Author(s):  
Yulei Zhao ◽  
Shuai Li ◽  
Yuhang Fan ◽  
Xuqiang Guo ◽  
Xin Jiao ◽  
...  
Keyword(s):  
Indole Derivatives ◽  
Intramolecular Cycloaddition

Hydroxylamines as One-Atom Nitrogen Sources for Metal-Catalyzed Cycloadditions

Synthesis ◽  
2021 ◽  
Author(s):  
Xinjun Luan ◽  
Jingxun Yu
Keyword(s):  
Transition Metal ◽  
Nitrogen Source ◽  
Nucleophilic Reagent ◽  
Nitrogen Sources ◽  
Short Review ◽  
Indole Derivatives ◽  
Electrophilic Amination ◽  
Intramolecular Cycloaddition ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

AbstractTransition-metal-catalyzed C–N bond formation is one of the most important pathways to synthesize N-heterocycles. Hydroxylamines can be transformed into a nucleophilic reagent to react with a carbon cation or coordinate with a transition metal; it can also become an electrophilic nitrogen source to react with arenes, alkenes, and alkynes. In this short review, the progress made on transition-metal-catalyzed cycloadditions with hydroxylamines as a nitrogen source is summarized.1 Introduction2 Cycloaddition To Form Aziridine Derivatives2.1 Intramolecular Cycloaddition To Form Aziridine Derivatives2.2 Intermolecular Cycloaddition To Form Aziridine Derivatives3 Cycloaddition To Form Indole Derivatives4 Cycloaddition To Form Other N-Heterocycles4.1 Aza-Heck-Type Amination Reactions4.2 Nitrene Insertion Amination Reactions4.3 Intramolecular Nucleophilic and Electrophilic Amination Reactions5 Conclusion and Outlook

Synthesis and Reactivity of Uhle’s Ketone and its Derivatives

Synthesis ◽  
2020 ◽  
Author(s):  
Francesca Bartoccini ◽  
Giovanni Piersanti
Keyword(s):  
Indole Alkaloids ◽  
Ring Expansion ◽  
Preparative Method ◽  
Structural Motif ◽  
Indole Derivatives ◽  
Carbonyl Carbon ◽  
Bioactive Substances ◽  
Intramolecular Cycloaddition ◽  
Bioactive Natural Products ◽  
The Subject

The Uhle’s ketone and its derivatives are highly versatile intermediates for the synthesis of a variety of 3,4-fused tricyclic indole frameworks, i.e. indole alkaloids of the ergot family, that are found in various bioactive natural products and pharmaceuticals. Therefore, the development of a convenient preparative method for this structural motif as well as its opportune/useful derivatization have been the subject of longstanding interest in the fields of synthetic organic chemistry and medicinal chemistry. Herein, we summarize recent and less recent methods for the preparation of Uhle’s ketone and its derivatives as well as its main reactivity towards the synthesis of bioactive substances. Regarding the preparation, it can be roughly classified into two categories: a) using 4-unfunctionalized and 4-functionalized indole derivatives as starting materials to construct a fused six-member ring, and b) constructing the indole ring through intramolecular cycloaddition. Principally, the reactivity of the cyclic Uhle’s ketone shown here is derived from the classical electrophilicity of the carbonyl carbon or the acidity of the α-hydrogen and, though less intensively investigated, chemical reactions that induce ring expansion to form novel ring skeletons.

ChemInform Abstract: Pyrazolo(1,5-a)indole Derivatives. Part 1. Intramolecular Cycloaddition of 2-Allylphenylhydrazones.

ChemInform ◽  
2010 ◽  
Vol 22 (1) ◽  
pp. no-no
Author(s):  
H. KATAYAMA ◽  
N. TAKATSU ◽  
H. KITANO ◽  
Y. SHIMAYA
Keyword(s):  
Indole Derivatives ◽  
Intramolecular Cycloaddition

scholarly journals Pyrazolo(1,5-a)indole derivatives. Part 1. Intramolecular cycloaddition of 2-allylphenylhydrazones.

1990 ◽  
Vol 38 (5) ◽  
pp. 1129-1135 ◽  
Author(s):  
Hajime KATAYAMA ◽  
Noriyuki TAKATSU ◽  
Haruko KITANO ◽  
Yukari SHIMAYA
Keyword(s):  
Indole Derivatives ◽  
Intramolecular Cycloaddition

Catalytic enantioselective synthesis of indolizino[8,7-b]indole alkaloid derivatives based on the tandem reaction of tertiary enamides

2021 ◽  
Author(s):  
Xin-Ming Xu ◽  
Ming Xie ◽  
Jiazhu Li ◽  
Mei-Xiang Wang
Keyword(s):  
Indole Alkaloid ◽  
Enantioselective Synthesis ◽  
High Yield ◽  
Tandem Reaction ◽  
Indole Derivatives

An exquisite Pybox/Cu(OTf)2-catalyzed asymmetric tandem reaction of tertiary enamides was developed, which enabled the expeditious synthesis of indolizino[8,7-b]indole derivatives in high yield, excellent enantioselectivity and diastereoselectivity.

Recent Developments on Synthesis of Indole Derivatives Through Green Approaches and Their Pharmaceutical Applications

2020 ◽  
Vol 24 (22) ◽  
pp. 2665-2693
Author(s):  
Dipayan Mondal ◽  
Pankaj Lal Kalar ◽  
Shivam Kori ◽  
Shovanlal Gayen ◽  
Kalpataru Das
Keyword(s):  
Biological Activities ◽  
Synthetic Methods ◽  
Pharmaceutical Chemistry ◽  
Indole Derivatives ◽  
Biological Studies ◽  
Recent Developments ◽  
Pharmaceutical Industries ◽  
Green Methodology ◽  
Conventional Methods ◽  
High Yields

Indole moiety is often found in different classes of pharmaceutically active molecules having various biological activities including anticancer, anti-viral, anti-psychotic, antihypertensive, anti-migraine, anti-arthritis and analgesic activities. Due to enormous applications of indole derivatives in pharmaceutical chemistry, a number of conventional synthetic methods as well as green methodology have been developed for their synthesis. Green methodology has many advantages including high yields, short reaction time, and inexpensive reagents, highly efficient and environmentally benign over conventional methods. Currently, the researchers in academia as well as in pharmaceutical industries have been developing various methods for the chemical synthesis of indole based compounds via green approaches to overcome the drawbacks of conventional methods. This review reflects the last ten years developments of the various greener methods for the synthesis of indole derivatives by using microwave, ionic liquids, water, ultrasound, nanocatalyst, green catalyst, multicomponent reaction and solvent-free reactions etc. (please see the scheme below). Furthermore, the applications of green chemistry towards developments of indole containing pharmaceuticals and their biological studies have been represented in this review.

C-3 Functionalization of Indole Derivatives with Isoquinolines

2016 ◽  
Vol 20 (20) ◽  
pp. 2038-2054 ◽  
Author(s):  
István Szatmári ◽  
Judit Sas ◽  
Ferenc Fülöp
Keyword(s):  
Indole Derivatives

Defensive Role of Plant-Derived Secondary Metabolites: Indole and Its’ Derivatives

2020 ◽  
Vol 9 (2) ◽  
pp. 78-88
Author(s):  
Mulugeta Mulat ◽  
Raksha Anand ◽  
Fazlurrahman Khan
Keyword(s):  
Biofilm Formation ◽  
Growth And Development ◽  
Functional Role ◽  
Plant Pathogens ◽  
Bacterial Species ◽  
Indole Derivatives ◽  
Resistance Level ◽  
Defensive Role ◽  
Insect Attack

The diversity of indole concerning its production and functional role has increased in both prokaryotic and eukaryotic systems. The bacterial species produce indole and use it as a signaling molecule at interspecies, intraspecies, and even at an interkingdom level for controlling the capability of drug resistance, level of virulence, and biofilm formation. Numerous indole derivatives have been found to play an important role in the different systems and are reported to occur in various bacteria, plants, human, and plant pathogens. Indole and its derivatives have been recognized for a defensive role against pests and insects in the plant kingdom. These indole derivatives are produced as a result of the breakdown of glucosinolate products at the time of insect attack or physical damages. Apart from the defensive role of these products, in plants, they also exhibit several other secondary responses that may contribute directly or indirectly to the growth and development. The present review summarized recent signs of progress on the functional properties of indole and its derivatives in different plant systems. The molecular mechanism involved in the defensive role played by indole as well as its’ derivative in the plants has also been explained. Furthermore, the perspectives of indole and its derivatives (natural or synthetic) in understanding the involvement of these compounds in diverse plants have also been discussed.

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