Potentiality and Synthesis of O- and N-Heterocycles: Pd-Catalyzed Cyclocarbonylative Sonogashira Coupling as a Valuable Route to Phthalans, Isochromans, and Isoindolines

被引：50

作者：

Albano, Gianluigi ^{[1
]}

Aronica, Laura Antonella ^{[1
]}

机构：

[1] Univ Pisa, Dipartimento Chim & Chim Ind, Via G Moruzzi 13, I-56124 Pisa, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 48期

关键词：

Carbonylation; Cross-coupling; Phthalans; Isochromans; Isoindolines; Oxygen heterocycles; Nitrogen heterocycles; DIELS-ALDER REACTION; FUNCTIONALIZED ORGANOLITHIUM COMPOUNDS; POLYCYCLIC AROMATIC-HYDROCARBONS; TRICYCLIC SULTAM LIBRARY; PICTET-SPENGLER REACTION; C-H FUNCTIONALIZATION; ONE-POT SYNTHESIS; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS;

D O I：

10.1002/ejoc.201701041

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 anti-mycotics, 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. Cyclo-carbonylative 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.

引用

页码：7204 / 7221

页数：18

共 398 条

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