Abstract:
Chromone-3-carboxamides react with cyanothioacetamide in the presence of NaOEt in boiling ethanol to form 5-oxo-2-thioxo-1,5-dihydro-2H-chromeno[4,3-b]pyridine-3-carbonitriles (67–87% yields), whereas their reaction with N-methylcyanothioacetamide and a catalytic amount of Et3N in boiling ethanol affords 5-cyano-2-(2-hydroxyphenyl)-1-methyl-6-thioxo-1,6-dihydropyridine-3-carboxamides in 57–73% yields.
Citation:
M. Yu. Kornev, D. S. Tishin, V. Ya. Sosnovskikh, “Reactions of chromone-3-carboxamides with 2-cyanothioacetamides”, Mendeleev Commun., 29:1 (2019), 67–68
Linking options:
https://www.mathnet.ru/eng/mendc1424
https://www.mathnet.ru/eng/mendc/v29/i1/p67
This publication is cited in the following 6 articles:
Magdy A. Ibrahim, Al-Shimaa Badran, “Novel Heteroannulated Chromeno[2,3-b]pyridines and Related Compounds Using 6-Methylchromone-3-carbonitrile”, HETEROCYCLES, 104:4 (2022), 707
Shrishnu Kumar Kundu, Susanta Patra, Chayan Sardar, Sunil Kumar Bhanja, Prasanta Patra, “Synthesis of 5H-Chromeno[4,3-b]pyridin-5-one derivatives as a backbone of natural product polyneomarline C scaffolds in presence of Et3N and NH4OAc in EtOH”, Chim.Tech.Acta, 9:2 (2022)
Nikita M. Chernov, Roman V. Shutov, Nadezhda Yu. Sipkina, Maxim N. Krivchun, Igor P. Yakovlev, “A Flexible Synthetic Approach to Fluorescent Chromeno[4,3‐b]pyridines and Pyrano[3,2‐c]chromenes from Electron‐Deficient 3‐Vinylchromones”, ChemPlusChem, 86:9 (2021), 1256
Prasanta Patra, Gandhi Kumar Kar, “The synthesis, biological evaluation and fluorescence study of chromeno[4,3-b]pyridin/quinolin-one derivatives, the backbone of natural product polyneomarline C scaffolds: a brief review”, New J. Chem., 45:6 (2021), 2879
Al-Shimaa Badran, Aya Ahmed, Magdy A. Ibrahim, “Chemical Transformation of Chromones into Coumarins”, HETEROCYCLES, 102:12 (2021), 2277
Dmitrii Y. Demin, Ksenia A. Myannik, Konstantin A. Lyssenko, Mikhail M. Krayushkin, Vladimir N. Yarovenko, “Synthesis of Polyfunctionalized Thiophenes and Pyrido[3,2‐c]Coumarines from 3‐Carbamoyl/3‐Thiocarbamoyl Chromones”, ChemistrySelect, 4:20 (2019), 6090
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