A Versatile and Regiospecific Synthesis of Functionalized 1,3-Diarylisobenzofurans

Abstract

A convenient, versatile, and regiospecific synthesis of functionalized 1,3-diarylisobenzofurans has been developed. It involves chemoselective addition of arylmagnesium reagents to the aldehyde function of o-aroylbenzaldehydes, themselves readily obtained by lead tetraacetate oxidation of N-aroylhydrazones of salicylaldehydes. Various functional groups, including nitro, iodo, or ester functionalities, have thus been positioned with complete regiospecificity on the 1,3-diphenylisobenzofuran backbone.

Diversity‐Oriented Synthesis of Calothrixins and Ellipticines

“…The mechanistic studies performed by Kotali and Katritzky showed that this rearrangement occurs through 1,3,4‐oxadiazoline and 1,3‐dioxane intermediates 7b. Einhorn et al8a and Dong et al8b also utilised this method for the synthesis of a range of o ‐diacylbenzenes. Although there are various reports on the formation of o ‐diacylbenzenes by LTA‐mediated oxidation, as mentioned above,7 so far this reaction has not been explored with heterocyclic aromatic compounds such as indoles, quinoline, and pyridines.…”

Structure and Dynamics of the Excited States of 1,3‐Diarylisobenzofurans: An Experimental and Theoretical Study

“…A series of variously substituted diphenylisobenzofurans was synthesized by a previously described versatile method (16). The studied molecules are represented in Fig.…”

“…The photochemical and photophysical properties of the IBFs are expected to be altered by the introduction of various substituents or functional groups at selected positions of the 1,3‐diarylisobenzofuran backbone. New versatile and regiospecific synthesis of functionalized IBF derivatives have been developed recently (15–17), giving a straightforward access to previously unknown compounds, and thus providing a library of diversely substituted IBFs. A thorough inspection of the events following the absorption of a photon is described hereafter.…”

Acid‐Induced Rearrangement of Cycloadducts from Cyclopropenecarboxylates and 1,3‐Diarylisobenzofurans

“…Hexane and AcOEt for the chromatography were distilled before use. Cyclopropenes and 1,3‐diarylisobenzofurans were prepared following known procedures . Reactions were monitored by the TLC analysis using Silufol UV‐254 plates.…”