Ketocalix[6]arene 2e was prepared by CrO3 oxidation of the methylene groups of 2a, followed by hydrolysis of the acetate groups. 2e undergoes intramolecular SNAr reactions under the usual methylation conditions (MeI, base), yielding mono- and dixanthone calixarene derivatives.
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http://dx.doi.org/10.1021/ol070870m | DOI Listing |
ACS Omega
November 2024
Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., Stavropol 355017, Russia.
A cascade transformation of C2-quaternary indoxyls leading to an efficient assembly of complex (dihydro)indolo[1,2-]quinolin-5-one ring systems is reported. The method involves the gram-scale preparation of 2-(2-aryl-3-oxoindolin-2-yl)-2-phenylacetonitriles which are then converted with methyl ketones to the corresponding 2-(2-oxo-2-aryl(alkyl)ethyl)-2-phenylindolin-3-ones. The latter can either be isolated with good yields (75-96%) or, in the case of -nitroacetophenone, used for further base-assisted intramolecular SAr cyclization resulting in indoxyl-fused quinolone-4 hybrids (up to 95%).
View Article and Find Full Text PDFYakugaku Zasshi
October 2024
Faculty of Pharmaceutical Sciences, Showa Pharmaceutical University.
Bioorg Chem
October 2024
Organic and Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology, 4, Raja S. C. Mullick Road, Kolkata 700032, India. Electronic address:
An unprecedented metal-free synthesis of fused quinoxaline 1,5-disubstituted-[1,4]-diazepine hybrids have been reported under mild conditions through a domino intermolecular SAr followed by an internal nucleophile-triggered intramolecular SAr pathway. Our strategy offers the flexibility for the introduction of a broad variety of functionalities at the N-1 position of fused diazepine moiety by using suitable diamine tails to design structurally diverse scaffolds. The DNA binding properties of representative quinoxaline diazepine hybrids were studied using UV-vis absorbance and EtBr displacement assay and were found to be governed by the functionalities at the N-1 position.
View Article and Find Full Text PDFJ Org Chem
August 2024
Department of Pharmaceutical Technology (Process Chemistry), National Institute of Pharmaceutical Education and Research, S. A. S. Nagar, Punjab 160062, India.
A reductive amidation of unactivated esters with nitroarenes, a key step in the telescopic synthesis of tetrahydropyrrolo[1,2-]quinoxalinones and tetrahydropyrido[1,2-]quinoxalinones, is reported. The process involves an intermolecular base-mediated SAr reaction, followed by intramolecular reductive amidation employing sodium dithionite. The substrate scope coupled with the demonstration of the synthesis of pharmaceuticals is reported.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
September 2024
Key Laboratory of Chemical Biology and Traditional Chinese Medicine, Ministry of Educational of China, Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha, 410081, China.
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