Potentiality and Synthesis of O‐ and N‐Heterocycles: Pd‐Catalyzed Cyclocarbonylative Sonogashira Coupling as a Valuable Route to Phthalans, Isochromans, and Isoindolines. Issue 48 (24th October 2017)

• Record Type: Journal Article
• Authors: Albano, Gianluigi; Aronica, Laura Antonella
• Is Part Of: European journal of organic chemistry. Issue 48(2017)
• Page Start: 7204
• Page End: 7221
• Publication Date: 2017-10-24
• Subjects: Carbonylation -- Cross‐coupling -- Phthalans -- Isochromans -- Isoindolines -- Oxygen heterocycles -- Nitrogen heterocycles; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201701041
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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. Abstract : This microreview covers the biological activities and chemical properties of phthalans, isochromans, and isoindolines, as well as the synthetic methodologies used for their preparation, with particular attention to application of cyclocarbonylative Sonogashira coupling for the preparation of alkylidene derivatives.