Investigation of the synthesis of isoindolene and isoquinoline derivatives

Abstract

Isoindoles and isoquinolines, as well as their isomers indoles and quinolines respectively are an essential class of heteroaromatic compounds. They attract the attention of many researchers due to their wide applications in different areas. The preparation of these heterocyclics from their first isolation until now, different methodologies applied, favor one method over others is depending on the easy of preparing them taking the time and toxicity and other factors in perspective. Recently there are different precursors which have been used to synthesis these heterocyclics in one step reaction which attract the attention to the ease of preparing them. This thesis will introduce isoquinoline and isoindole briefly, followed by their applications in which participate in various areas. After that, it will focus on the precursors which are recently used to synthesize them in different conditions such as catalyst, for example, Copper, Zinc, Titanium, Lanthanide, Palladium. When different types of amines applied, the outcome of preparation of isoquinoline and isoindoles seems affected by the type of the amines, some give a good yield while others give mixtures. The ring closure, whether 5-Exo-dig or 6-endo-dig of these precursors is affected by the catalysts. Therefore, (z)-1-(4-Methoxyphenylmethylene)-1H-isoindol-3-amine has been synthesized by using 2-bromobenzonitrile and 4-ethynylanisole in the presence of palladium PdCl2(MeCN)2. Introducing Copper to this reaction conditions lead to the promoting of homocoupling product and other unknown products. 3-(p-Methoxyphenyl)isoquinolin-1-amine 33 and (Z)-2-(4-Methoxystyryl)benzonitrile 34 are obtained from treatment of 2-alkynylbenzonitrile and Pd(OAc)2 and KOAc and NH4OAc and PPh3 and DMF in microwave vial that placed in a preheated oil bath at 150 oC producing 33 and 34. The reaction takes a long time as well as the starting materials remain. Different optimization was utilized producing 33 and 34 with no presence of starting materials as well as the time is shortened.