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

From Alkynes to Heterocycles through Metal-Promoted Silylformylation and Silylcarbocyclization Reactions

“…We really hope that the present review may stimulate further research in the field of silylformylation and silylcarbocyclization reactions, and in particular for the preparation of new biologically relevant Oand N-heterocycles, as a valid alternative to the most common cycloaddition [110][111][112] or cross-coupling reactions [113][114][115][116]. Moreover, the recent studies on CO surrogates [117][118][119] may be a strong stimulus for innovative and safer development of new silylcarbonylation processes.…”

“…Synthesis of tosylindolinols and tosyltetrahydroisoquinolinols via heteroatom-promoted SiCAC with several ArMe2SiH. and N-heterocycles, as a valid alternative to the most common cycloaddition [110][111][112] or cross-coupling reactions [113][114][115][116]. Moreover, the recent studies on CO surrogates [117][118][119] may be a strong stimulus for innovative and safer development of new silylcarbonylation processes.…”

Supported Metal Catalysts for the Synthesis of N-Heterocycles

“…Nitrogen-containing heterocycles represent important scaffolds for a large number of natural products [1,2], biologically active compounds with pharmaceutical interest [3,4], materials for chemical industry (e.g., pigments in paints, varnishes and plastics) [5] and organic optoelectronics (e.g., polymeric active layers for electroluminescent devices or organic photovoltaic cells) [6][7][8]. This explains the great and continuous interest of the Organic Chemistry community in the development of efficient and convenient methodologies for the preparation of N-heterocycles [9][10][11][12].…”

Organocatalytic Synthesis of Highly Functionalized Heterocycles by Enantioselective aza-Morita–Baylis–Hillman-Type Domino Reactions

“…[41][42][43][44][45][46][47][48][49][50][51][52] 41,42) Isoindoline skeletons are standard structures in a variety of natural products and pharmaceuticals, such as nuevamine 53) and pagoclone, 54) as well as their functionalized derivatives. 55) As such, these materials show a range of biological potencies involving anti-leukemic, anxiolytic, anti-tumoral, and potent endothelin A receptor antagonist activities. [53][54][55] Due to the numerous potential applications of these heterocycles, the development of efficient and novel synthetic approaches for isoindolines has received special attention.…”

“…55) As such, these materials show a range of biological potencies involving anti-leukemic, anxiolytic, anti-tumoral, and potent endothelin A receptor antagonist activities. [53][54][55] Due to the numerous potential applications of these heterocycles, the development of efficient and novel synthetic approaches for isoindolines has received special attention. 56) However, very few studies have addressed the catalytic preparation of 1,3disubstituted isoindolines.…”