scholarly journals Synthesis of Medium-Sized Heterocycles by Transition-Metal-Catalyzed Intramolecular Cyclization

Molecules ◽  
2020 ◽  
Vol 25 (14) ◽  
pp. 3147 ◽  
Author(s):  
Mickael Choury ◽  
Alexandra Basilio Lopes ◽  
Gaëlle Blond ◽  
Mihaela Gulea
Keyword(s):  
Transition Metal ◽  
Intramolecular Cyclization ◽  
Biologically Active ◽  
Conformational Constraints ◽  
Synthesis Strategy ◽  
Gold Silver ◽  
Copper Gold ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed ◽  
Active Natural

Medium-sized heterocycles (with 8 to 11 atoms) constitute important structural components of several biologically active natural compounds and represent promising scaffolds in medicinal chemistry. However, they are under-represented in the screening of chemical libraries as a consequence of being difficult to access. In particular, methods involving intramolecular bond formation are challenging due to unfavorable enthalpic and entropic factors, such as transannular interactions and conformational constraints. The present review focuses on the synthesis of medium-sized heterocycles by transition-metal-catalyzed intramolecular cyclization, which despite its drawbacks remains a straightforward and attractive synthesis strategy. The obtained heterocycles differ in their nature, number of heteroatoms, and ring size. The methods are classified according to the metal used (palladium, copper, gold, silver), then subdivided according to the type of bond formed, namely carbon–carbon or carbon–heteroatom.

scholarly journals Transition-metal-catalyzed intramolecular cyclization of amido(hetero)arylboronic acid aldehydes to isoquinolinones and derivatives

RSC Advances ◽  
2015 ◽  
Vol 5 (26) ◽  
pp. 20108-20114 ◽  
Author(s):  
C. S. Marques ◽  
D. Peixoto ◽  
A. J. Burke
Keyword(s):  
Transition Metal ◽  
Intramolecular Cyclization ◽  
Arylboronic Acid ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

We report an innovative and simple three step high yielding synthesis of a library of 14 chiral isoquinolinone and azepinone derivatives with benzyl, pyridyl and thiophene cores starting from amidoarylboronic acid aldehydes.

scholarly journals Recent Advances in Transition Metal-Catalyzed Reactions of Oxabenzonorbornadiene

2019 ◽  
Vol 16 (4) ◽  
pp. 460-484 ◽  
Author(s):  
Rebecca Boutin ◽  
Samuel Koh ◽  
William Tam
Keyword(s):  
Transition Metal ◽  
Structural Features ◽  
Metal Catalysts ◽  
Single Step ◽  
Transition Metal Catalysts ◽  
Biologically Active ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed ◽  
Work Done

Background: Oxabenzonorbornadiene (OBD) is a useful synthetic intermediate capable of undergoing multiple types of transformations due to three key structural features: a free alkene, a bridged oxygen atom, and a highly strained ring system. Most notably, ring-opening reactions of OBD using transition metal catalysts and nucleophiles produce multiple stereocenters in a single step. The resulting dihydronaphthalene framework is found in many natural products, which have been shown to be biologically active. Objective: This review will provide an overview of transition metal-catalyzed reactions from the past couple of years including cobalt, copper, iridium, nickel, palladium and rhodium- catalyzed reactions. In addition, the recent derivatization of OBD to cyclopropanated oxabenzonorbornadiene and its reactivity will be discussed. Conclusion: It can be seen from the review, that the work done on this topic has employed the use of many different transition metal catalysts, with many different nucleophiles, to perform various transformations on the OBD molecule. Additionally, depending on the catalyst and ligand used, the stereo and regioselectivity of the product can be controlled, with proposed mechanisms to support the understanding of such reactions. The use of palladium has also generated a cyclopropanated OBD, with reactivity similar to that of OBD. An additional reactive site exists at the distal cyclopropane carbon, giving rise to three types of ring-opened products.

Recent Advances in the Transition Metal Catalyzed Addition of Carboxylic Acids to Alkynes

2021 ◽  
Vol 25 ◽  
Author(s):  
Victorio Cadierno
Keyword(s):  
Natural Products ◽  
Transition Metal ◽  
Carboxylic Acids ◽  
Heterocyclic Compounds ◽  
Biologically Active ◽  
Recent Advances ◽  
Enol Esters ◽  
Cascade Processes ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

: Recent advances in the metal-catalyzed hydrofunctionalization of alkynes with carboxylic acids are comprehensively reviewed. Both inter- and intramolecular processes, leading respectively to enol esters and lactones, are discussed, as well as the involvement of these transformations in the synthesis of natural products and biologically active molecules, and the assembly of elaborated heterocyclic compounds though cascade processes. Literature published since 2011 is covered.

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