Abstract
4,4′-(1,3-Phenylenebis(oxy))dianiline 1 is an aromatic diamine compound and has been very less utilized in the organic synthesis. Different diimines and diamides were synthesized by reacting compound 1 with aromatic and heterocyclic compounds having different functionalities. These longer electron rich spacer molecules were synthesized to utilize them in the near future in making macrocycles of different sizes and functionalities. A hydrazide was also prepared from a diamide spacer molecule containing ester group. A diamide prepared containing nibrobenzene moiety was further reduced to amine to obtain longer spacer diamine molecule than the starting molecule 1.
Highlights
The condensation of primary amines with carbonyl group was discovered in 1864 by Schiff [1] and has been always the reaction of interest to chemists up to date in the fields of macrocyclic and supramolecular chemistry
Different units containing amide bond were synthesized by reacting acyl halides and esters with diamine 1
Amide units synthesized from acyl chlorides were easy to give amide containing compounds as compared to esters
Summary
The condensation of primary amines with carbonyl group was discovered in 1864 by Schiff [1] and has been always the reaction of interest to chemists up to date in the fields of macrocyclic and supramolecular chemistry. The more interesting case is the cyclization of dicarbonyl compounds with diamines which can produce verity of products like [1+1]condensation, [2+1]-condensation or [1+2]-condensation products, and so forth These types of reactions lead to macrocylization after [2+2]-condensation occurs. Leading towards different topologically important macrocycles, two different types of macrocycles were the targets These macrocycles can be electron donors, that is, macrocycles having electron rich heteroatoms and having the donating power to catch or cage the cation inside the ring which can be used as artificial ion channel for cations in the future. For the synthesis of donor macrocycles, many units were synthesized which can be used as electrophiles or nucleophile These groups will be used in different combinations to make macrocycles. These units can be divided into three subgroups according to the functional groups they have, for example, amides, imines, and other units
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