Transition Metal-Catalyzed Intramolecular Cyclization of Propargyl Alcohols and Their Derivatives for the Synthesis of Highly Substituted Five-Membered Oxygen Heterocycles

The most recent advances in the construction of oxygen heterocycles by the directing-group-assisted transition-metal-catalyzed direct oxidative annulation of arenes with diverse alkynes are summarized in this review. More than 140 recent research papers and many closely related reviews are referenced in this paper. Nine different oxygen heterocycles frameworks are discussed. Several traditional transition-metal catalysts as well as some classical non-noble metals are utilized to promote the annulation. Three plausible controlling models are disclosed to clarify the excellent regioselectivity outcomes achieved in case of unsymmetrical alkyne substrates.1 Introduction2 Coumarins3 I socoumarins and Their Analogues4 2-Pyrones and Their Analogues5 Chromones and Chroman-4-ones6 Chromenes and Isochromenes7 Fused Polycyclic Oxygen Heteroaromatics8 Benzofurans, Dihydrobenzofurans, and Furans9 Phthalides and Benzofuranones10 Benzoxepines11 Conclusion

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

Molecules ◽

10.3390/molecules25143147 ◽

2020 ◽

Vol 25 (14) ◽

pp. 3147 ◽

Cited By ~ 3

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.

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

RSC Advances ◽

10.1039/c5ra00404g ◽

2015 ◽

Vol 5 (26) ◽

pp. 20108-20114 ◽

Cited By ~ 11

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.

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