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An Efficient Method for the Synthesis of New Non‐Symmetrical Naphthalenediimides
Author(s) -
AlatorreBarajas José A.,
RamírezZatarain Sandy D.,
OchoaTerán Adrián,
Cordova Jesus,
ReynosoSoto Edgar A.,
Chávez Daniel,
MirandaSoto Valentín,
LabastidaGalván Victoria,
Ordoñez Mario
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201802168
Subject(s) - toluene , imide , regioselectivity , yield (engineering) , chemistry , solvent , organic chemistry , medicinal chemistry , catalysis , materials science , metallurgy
Abstract Herein we report an efficient synthesis of a series of non‐symmetrical naphthalenediimides (NDIs) bearing different neutral, electron‐donating and electron‐withdrawing groups in the imide moieties. The success of this method is based in the regioselective synthesis and isolation of pure carbamoyl naphthoic anhydride acid intermediates (CNA) in good yields (54 to 99%) and high purity, from the reaction of naphthalenetetracarboxylic dianhydride acid (NDA) with one equivalent of different primary amines and THF as solvent. The CNA intermediates were refluxed in toluene and gave the naphthalenemonoimides (NMI) in 55 to 89% yields and high purity. The N ‐benzyl NMI was used as starting material in the synthesis of non‐symmetrical NDIs ( 1 a ‐ m ) in 27 to 80% yield with several amines bearing different substituted benzylic groups. In addition, this methodology was extended to obtain other new NDIs ( 1 n‐r ) in good yields (67‐90%) and purity.