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Potentiality and Synthesis of O‐ and N‐Heterocycles: Pd‐Catalyzed Cyclocarbonylative Sonogashira Coupling as a Valuable Route to Phthalans, Isochromans, and Isoindolines
Author(s) -
Albano Gianluigi,
Aronica Laura Antonella
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701041
Subject(s) - isoindoline , sonogashira coupling , chemistry , combinatorial chemistry , nitrogen atom , catalysis , organic chemistry , palladium , ring (chemistry)
Oxygen and nitrogen heterocycle systems are found in a vast number of natural substrates and biologically active molecules. In particular, phthalan, isochroman, and isoindoline scaffolds are present in many classes of products such as antimycotics, antibiotics, antioxidants, pigments, and fluorophores. Therefore several procedure dedicated to the building of such heterocycles have been developed. In this review a detailed analysis of literature data relating to these scaffolds is described. Particular attention has been devoted to their biological and chemical potentiality, and an in‐depth investigation into the most important synthetic methods is reported. Cyclocarbonylative Sonogashira coupling of suitable alcohols and amides has been carefully considered, because it represents a valuable and atom‐economic route for the construction of alkylidenephthalans, ‐isochromans, and ‐isoindolines.