A novel one-pot multicomponent synthesis of α-aminocarbonyl N-acylhydrazones starting from readily available hydrazonoyl chlorides, isocyanides, and carboxylic acids is reported. The strategy exploits the ability of the carboxylic acid as a third component to suppress all competing reactions between nitrile imines and isocyanides, channeling the course of the reaction toward the formation of this novel class of compounds.
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http://dx.doi.org/10.1021/ol502515b | DOI Listing |
Sci Rep
November 2024
Applied Organic Chemistry Department, National Research Centre, Dokki, 12622, Cairo, Egypt.
Future Med Chem
October 2024
Department of Organic & Medicinal Chemistry, Faculty of Pharmacy, University of Sadat City, 32897, Egypt.
This research aims to expand the established pharmacological space of tumor-associated carbonic anhydrases (TACAs) by exploring the synthetically accessible chemical space of 3-substituted coumarins, with the help of pharmacology prediction. 52 novel 3-substituted coumarins were sketched, prioritizing synthetic feasibility. Their pharmacological potentials were estimated using a custom machine-learning approach.
View Article and Find Full Text PDFOrg Biomol Chem
September 2024
Gansu International Scientific and Technological Cooperation Base of Water-Retention Chemical Functional Materials, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, China.
Aromatic 1,2,4-diazaphospholes featuring distinct hybrid-mode nitrogen atoms (N(λσ), N(λσ)) and low-valent phosphorus atoms (λσ) exhibited the characteristic of serving as unique hybrid ligands. This study presented a one-pot reaction involving the base-promoted stepwise cyclization of hydrazonoyl chlorides and [BuN][P(SiCl)] to yield 1,2,4-diazaphospholes, providing an effective method for synthesizing such compounds.
View Article and Find Full Text PDFRSC Adv
August 2024
Department of Chemistry, Faculty of Science, Cairo University Giza 12613 Egypt +202 35727556 +202 35676602.
A series of novel piperazine-based bis(thiazoles) 13a-d were synthesized in moderate to good yields reaction of the bis(thiosemicarbazones) 7a, b with an assortment of -acetyl--aryl-hydrazonoyl chlorides 8a-f. Similar treatment of the bis(thiosemicarbazone) 7a, b with -aryl--phenylhydrazonoyl chlorides 10a, b afforded the expected bis(thiadiazole) based piperazine products 13b-d in reasonable yields. Cyclization of 7a, b with two equivalents of α-haloketones 14a-d led to the production of the corresponding bis(4-arylthiazol)piperazine derivatives 15a-h in good yields.
View Article and Find Full Text PDFCurr Org Synth
July 2024
Department of Pharmaceutical Sciences, School of Pharmacy, The University of Jordan, Amman, 11942, Jordan.
Background: Hydrazonoyl chloride, accessible from the respective 5-amino-8-fluoro- 4-oxoquinoline-3-carboxylate, undergoes a reaction with sec-cyclic amines to generate N1-(1- ethyl-8-fluoro-4-oxoquinolin-5-yl)amidrazone carboxylates.
Introduction: A novel set of N1-(1-ethyl-8-fluoro-4-oxoquinolin-5-yl)amidrazone carboxylates (7a-h) incorporating N-piperazines or related congeners was synthesized interaction of the hydrazonoyl chloride (6), accessible from the respective 5-amino-8-fluoro-4-oxoquinoline-3-carboxylate, with the appropriate sec-cyclic amine. These new compounds were characterized by HNMR, C-NMR, and HRMS spectral data and screened for their anticancer activities.
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