An efficient approach to synthesize N-aryl pyrroles via Lewis acid-mediated 1,5-hydride shift and isomerization of 2-(3-pyrroline-1-yl)arylaldehydes has been achieved in up to 89% yield. This methodology is applicable to the synthesis of fluorazene derivatives as electron donor (D)/acceptor (A) molecules.
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http://dx.doi.org/10.1039/c4ob02009j | DOI Listing |
Chem Asian J
January 2025
Department of Chemistry, Indian Institute of Technology Guwahati, Assam, 781039, India.
An asymmetric synthesis of C-N atropisomers with pyrrole, oxindole and succinimide moities was developed via organocatalytic desymmetric Michael addition of 3-pyrrolyloxindole with prochiral N-aryl maleimides. The C-N atropisomers were obtained in acceptable yields with high diastero- and enantioselectivities (>20 : 1 dr, up to >99 % ee). C-N Rotational energy barrier has also been determined.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
September 2024
Instituto Investigaciones Químicas (CSIC-US), Centro de Innovación en Química Avanzada (ORFEO-CINQA), C/ Américo Vespucio 49, 41092, Sevilla, Spain.
A ruthenium-catalyzed reductive amination via asymmetric transfer hydrogenation (ATH) has been used to perform an efficient dynamic kinetic resolution (DKR) of N-aryl 2-formyl pyrroles decorated with a phosphine moiety positioned at the ortho' position. The strategy relies on the labilization of the stereogenic axis in the substrate facilitated by a transient Lewis acid-base interaction (LABI) between the carbonyl carbon and the phosphorus center. The reaction features broad substrate scope of aliphatic amines and N-aryl pyrrole scaffolds, and proceeds under very mild conditions to afford P,N atropisomers in good to high yields and excellent enantioselectivities (up to 99 % ee) for both diphenyl and dicyclohexylphosphino derivatives.
View Article and Find Full Text PDFJ Org Chem
April 2024
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, Warsaw 01-224, Poland.
A straightforward route to 1,4-dihydropyrrolo[3,2-]pyrroles comprised of two electron-withdrawing quinoline or tetrazolo[1,5-]quinoline scaffolds has been developed. The versatile multicomponent reaction affording 1,4-dihydropyrrolo[3,2-]pyrroles combined with intramolecular direct arylation enables assembly of these products in just three steps from anilines with overall yields exceeding 30%. The planarized, ladder-type heteroacenes possess up to 14 conjugated rings.
View Article and Find Full Text PDFBioorg Chem
April 2024
Department of Medicinal Chemistry, Faculty of Pharmacy, Minia University, 61519 Minia, Egypt. Electronic address:
Two new series of N-aryl acetamides 6a-o and benzyloxy benzylidenes 9a-p based 2-oxoindole derivatives were designed as potent antiproliferative multiple kinase inhibitors. The results of one-dose NCI antiproliferative screening for compounds 6a-o and 9a-p elucidated that the most promising antiproliferative scaffolds were 6f and 9f, which underwent five-dose testing. Notably, the amido congener 6f was the most potent derivative towards pancreatic ductal adenocarcinoma MDA-PATC53 and PL45 cell lines (IC = 1.
View Article and Find Full Text PDFJ Org Chem
January 2024
School of Chemical Engineering and Technology, Sun Yat-sen University, Zhuhai 519082, P. R. China.
A general and efficient CuI/-carbazolyl-1-pyrrole-2-carbohydrazide catalyst system was developed for the -arylation of cyclopropylamine using aryl bromides at room temperature. Herein, 5 mol % CuI and 5 mol % of the ligand were used to synthesize -aryl cyclopropylamines in moderate to excellent yields. This protocol was scaled up to produce the desired product at gram levels and has been generalized for C-N coupling between aryl bromides and amines at room temperature.
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