Cyclization Reactions for the Synthesis of Phthalans and Isoindolines­

Abstract

Oxygen and nitrogen heterocycles are present in a vast number of natural substrates and biologically active molecules. In particular, phthalan and isoindoline subunits are found in many classes of products such as antibiotics, antioxidants, antimycotics, pigments, and fluorophores. Therefore several procedures dedicated to the construction of these heterocycles have been developed. In this review, a detailed analysis of the literature data regarding the synthesis of these nuclei via cyclization reactions is reported.1 Introduction2 Phthalans2.1 Oxa-Pictet–Spengler Reaction2.2 Garratt–Braverman Cyclization2.3 Diels–Alder and Related Reactions2.4 [2+2+2] Cyclotrimerization of Alkynes2.5 Cycloetherification of ortho-Substituted Aromatics2.6 Tandem Carbonylative Sonogashira Coupling–Cyclization Reactions3 Isoindolines3.1 Amination of Dihalides3.2 Intramolecular Hydroamination3.3 Diels–Alder and Related Reactions3.4 [2+2+2] Cycloaddition Reactions3.5 Tandem Carbonylative Sonogashira Coupling–Cyclization Reactions4 Conclusions