Synthesis of isoindoles and related iso-condensed heteroaromatic pyrroles

Abstract

Over the past few years, isoindoles have found wide application in materials science. Isoindole containing BODIPY dyes are highly fluorescent materials and have been extensively used in various fields of science. Phthalocyanines, metal containing cyclic tetramers of isoindole, form coordination complexes with most elements of the periodic table. These complexes are intensely coloured and are used as pigments and dyes. However, isoindoles are relatively unstable 10π-heteroaromatic systems and few synthetic methods provide these compounds in good yields. This tutorial review will give an overview of the reported synthetic methods towards isoindoles and related heteroaromatic systems over a time span of approximately 10 years (2000 to current), including the applications where they have been reported. The importance of the field will be illustrated and factors influencing product stability will be discussed.

Picomolar Inhibitors of HIV Reverse Transcriptase Featuring Bicyclic Replacement of a Cyanovinylphenyl Group

“…7a, 7d, 7e , and 7b represent a ‘nitrogen walk’ around the 5-membered ring; the remaining isoindole isomer was excluded as such structures are labile. 20 Furthermore, benzothiophenes were not considered as they appeared less promising in initial structure building than the benzofurans, and they are both prone to have metabolic liabilities. 8 It was also anticipated that a substituent R” would be utilized as indicated in 5 , so the methylated analogs 7l – 7r were modeled.…”

An efficient synthesis of N-substituted pyrroles catalyzed by MgI2 etherate

“…In view of their important significance, preparation of pyrroles has attracted considerable attention of chemists in recent years. Many methodologies have been developed for the construction of the pyrrole moiety regarded as skeleton (Fang et al, 2012;Heugebaert et al, 2012). Among them, the Paal-Knorr synthesis remains the most useful preparative method for generating pyrroles (Aghapoor et al, 2012;Balme, 2012;Rahmatpour, 2012).…”

Convenient Synthesis of Novel Nitrogen Bridgehead Heterocycles Utilizing 3‐Mercapto‐6H‐[1,2,4,5]oxatriazino[3,2‐a]isoindol‐6‐one as a New Synthon

“…Thus, herein, we report coalescing of isoindole, azine, and azole moieties in single molecules. Isoindole‐based compounds construct one of the most impressive classes of compounds in organic chemistry, so they have attracted scientists for a long time and can be seen in diverse natural and pharmaceutical compounds . In addition, isoindoles have found interesting applications as dyes and a marker in analytical chemistry (staining of primary amines) .…”