A suitable and effective Q-tube-assisted strategy for the synthesis of novel, unrivalled thiochromeno[4,3-]pyridine and chromeno[4,3-]pyridine derivatives has been sophisticated, which includes ammonium acetate-mediated cyclocondensation reactions between 3-oxo-2-arylhydrazonopropanals and heterobenzocyclic ketones such as thiochroman-4-one and chroman-4-one, respectively. The high-pressure Q-tube reactor was shown to be superior to conventional heating. Furthermore, this Q-tube reactor-assisted protocol is safe owing to facile pressing and sealing, a broad substrate scope, and simple work-up and purification processes, as well as being scalable and having a high atom economy. The proposed mechanistic route includes two sequential dehydrative stages. In this investigation, X-ray crystallographic analysis was performed to authenticate the targeted products.
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http://dx.doi.org/10.1021/acsomega.1c05347 | DOI Listing |
ACS Omega
December 2021
Chemistry Department, Faculty of Science, Kuwait University, P.O. Box 5969, Safat 13060, Kuwait.
A suitable and effective Q-tube-assisted strategy for the synthesis of novel, unrivalled thiochromeno[4,3-]pyridine and chromeno[4,3-]pyridine derivatives has been sophisticated, which includes ammonium acetate-mediated cyclocondensation reactions between 3-oxo-2-arylhydrazonopropanals and heterobenzocyclic ketones such as thiochroman-4-one and chroman-4-one, respectively. The high-pressure Q-tube reactor was shown to be superior to conventional heating. Furthermore, this Q-tube reactor-assisted protocol is safe owing to facile pressing and sealing, a broad substrate scope, and simple work-up and purification processes, as well as being scalable and having a high atom economy.
View Article and Find Full Text PDFJ Org Chem
January 2018
Chemical Sciences and Technology Division, CSIR-National Institute for Interdisciplinary Science and Technology (NIIST), Thiruvananthapuram 695 019, India.
A simple and efficient one-pot annulation of arylidenones, alkynes, and nitriles in the presence of BF·OEt is described. A highly functionalized variety of N-substituted pyridine-fused chromeno and pyrano derivatives were obtained with satisfactory yields under mild reaction conditions. The method was proven to be valid for the synthesis of a diverse library of chromeno[3,4-c]pyridines, thiochromeno[3,4-c]pyridines, pyrano[3,4-c]pyridines, and thiopyrano[3,4-c]pyridine derivatives from readily accessible substrates.
View Article and Find Full Text PDFActa Crystallogr Sect E Struct Rep Online
March 2008
College of Chemistry and Molecular Engineering, Qingdao University of, Science and Technology, Qingdao 266042, People's Republic of China.
In the crystal structure of the title compound, C(24)H(14)Cl(3)NO(2)S, the tetra-hydro-pyridine ring adopts a half-chair conformation and both pendant benzene rings are oriented nearly perpendicular to the thio-chromeno[2,3-b]pyridine system.
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