A newly synthesized N,N'-dipropyl-substituted isoindigo derivative, namely, 1-propyl-3-(1-propyl-1,2-dihydro-2-oxo-3H-indol-3-ylidene)-1,3-dihydro-2H-indol-2-one, CHNO, was found to have three polymorphic forms (denoted Forms I, II and III) under various crystallization conditions. Crystal structure analysis indicated that Form III had a significantly different molecular conformation from the other two polymorphs. Their different packing arrangements were correlated with differences in the intermolecular interactions. Thermal measurements revealed that Forms I and II are enantiotropically related, and Form II exhibits thermally dynamic behaviour.
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http://dx.doi.org/10.1107/S2053229624002481 | DOI Listing |
Org Biomol Chem
November 2024
College of Chemistry and Chemical Engineering, Taishan University, Tai'an, Shandong, 271000, P. R. China.
The first example of an efficient protocol for the reduction of disubstituted methyleneindolinones, isoindigos and tetrasubstituted olefins for the synthesis of 3-substituted 2-oxindoles, dihydroisoindigos and tetrasubstituted ethane derivatives using an L-amino acid ester as an attractive biomimetic reducing agent has been developed. This new protocol has the advantages of mild reaction conditions without the need for any metal catalysts, a broad substrate scope (31 examples), excellent yields (90-98%) and good functional group tolerance, providing an operationally simple and practically useful methodology for reductive reactions. The L-amino acid derivative, which is cheap, nontoxic and easy to handle, serves as a new biomimetic reducing agent for use in organic chemistry, providing a novel and promising approach for future applications in reductive reactions.
View Article and Find Full Text PDFBeilstein J Org Chem
November 2024
Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany.
Indigo, indirubin, and isoindigo derivatives have been used for centuries as pigments. Since the 1990s, a new aspect of the chemistry of this type of compounds is their activity against various types of cancer. -Glycosides of indigo, indirubin, and isoindigo, blue, red, and yellow sugars, turned out to be of special interest because of their high cancerostatic activity and structural novelty.
View Article and Find Full Text PDFChemistry
December 2024
Key Laboratory of Optoelectronic Chemical Materials and Devices, School of Optoelectronic Materials & Technology, Ministry of Education, Jianghan University, Wuhan, 430056, P. R. China.
Isoindigo, an electron-withdrawing building block for polymeric field-effect transistors, has long been considered to be non-fluorescent. Moreover, using electron-deficient heterocycle to replace the phenyl ring in the isoindigo core for better electron transport behaviour is synthetically challenging. Here we report the syntheses of a series of tetrazaisoindigos, including pyrazinoisoindigo (PyrII), pyrimidoisoindigo (PymII) and their hybrid (PyrPymII), and the investigation on their photophysical and electric properties.
View Article and Find Full Text PDFOrg Biomol Chem
April 2024
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China.
Considering the importance of developing powerful catalysts and the pharmacophore characteristics of indole derivatives, we describe a switchable approach for the iron-catalyzed oxidative C(sp)-H functionalization of indolin-2-ones. Selective transformations displayed excellent activity and chemoselectivity using FeCl as the catalyst, air as the oxidant, and alcohol as the solvent. By manipulating the reaction conditions, particularly the choice of solvent, catalyst loading, and reaction sequence, a series of valuable indole derivatives, including isatins and symmetrical and nonsymmetrical isoindigos, were selectively synthesized in good to excellent yields.
View Article and Find Full Text PDFActa Crystallogr C Struct Chem
April 2024
Graduate School of Environment and Information Sciences, Yokohama National University, 79-7 Tokiwadai, Yokohama 240-8501, Japan.
A newly synthesized N,N'-dipropyl-substituted isoindigo derivative, namely, 1-propyl-3-(1-propyl-1,2-dihydro-2-oxo-3H-indol-3-ylidene)-1,3-dihydro-2H-indol-2-one, CHNO, was found to have three polymorphic forms (denoted Forms I, II and III) under various crystallization conditions. Crystal structure analysis indicated that Form III had a significantly different molecular conformation from the other two polymorphs. Their different packing arrangements were correlated with differences in the intermolecular interactions.
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