Synthesen in der heterocyclischen Reihe, XV. Über 1‐[3‐Aryl‐isoindolyl‐(1)‐imino]‐3‐aryl‐1H‐isoindole

Abstract

Synthesen in der heterocyclischen Reihe, XV 2) ijber 1-[3-Aryl-isoindolyl-(l)-i1nino]-3-aryl-lH-isoindoleAus o-Cyan-benzophenon und Formamid erhalt man neben 3-Formamino-I-0x0-3-phenylisoindolin (5) das rotviolette I-[3-Phenyl-isoindolyl-(l)-imino]-3-phenyl-lH-isoindol (I).1 sowie an den Phenylkernen substituierte Analoga von 1 entstehen aus Phthalodinitrilen und Arylmagnesiumbromiden. Syntheses in the Heterocyclic Series, XVz) l-(3-Arylisoindol-l-ylimino)-3-aryl-lH-isoindoleso-Cyanobenzophenone reacts with formamide to give 3-formylamino-I-0x0-3-phenylisoindoline (5) and the redviolet 3-phenyl-l-(3-phenylisoindol-l -ylimino)-1 H-isoindole (1). Analogues of 1 substituted in the phenyl rings are obtained by treatment of phthalodinitriles with arylmagnesium bromides.

Azadipyrromethenes: from traditional dye chemistry to leading edge applications

“…21 Alternatively, the product could be obtained by reacting 2-cyanobenzophenone 27 with formamide, but in this case the yield was lower at 10%. 21 More recently, Riede and co-workers optimized these conditions and suggested a plausible mechanism for the formation of the azadiisoindolynmethane (Scheme 12). 22 The optimal conditions found were the addition of 1 equiv.…”

Synthesis and Characterization of Near‐Infrared Absorbing Benzannulated Aza‐BODIPY Dyes

“…[15] In the first method, compound 1 was treated with aryl magnesium bromides. After steam distillation and recrystallization of the crude product from pyridine, the aza-diisoindolmethines 9 were isolated in low yields.…”

“…Synthesis: The synthesis of aza-diisoindolmethines and their corresponding boron difluoride complexes D reported in the literature either start from phthalodinitrile (1) or from 2-cyanobenzophenone (4). [15] In the first method, compound 1 was treated with aryl magnesium bromides. After steam distillation and recrystallization of the crude product from pyridine, the aza-diisoindolmethines 9 were isolated in low yields.…”

“…[12][13][14] Thus, the treatment of 1-phenylisoindole with nitrous acid results in an oxidative dimerization as well as a ring-opening reaction of the starting material, instead of the formation of the corresponding 3-nitroso derivative as an intermediate for D. [13,14] Nevertheless, a few aza-diisoindolmethines D have been prepared, but the applied preparation method suffers from very low yields. [11,15] Hence, to date, no large series of aza-diisoindolmethines D has been synthesized and investigated.…”

From Fluorine to Fluorene—A Route to Thermally Stable aza‐BODIPYs for Organic Solar Cell Application

“…As the reproduction of the literature procedure for the complexation reaction of 1a -c led to signifi cant amounts of unreacted starting material and decomposition, this step was optimized by using higher excess of base (10 equivalents (eq.)) [ 12 ] After further adjustment of the amount of solvent, the literature yields could be signifi cantly increased to 80%-90% for all three BF 2 -complexes. as well as by carrying out the reaction in dichloromethane at room temperature overnight.…”