One-pot synthesis of functionalized benzo[c]coumarins and their precursors via the reaction of 2-(polyfluoroalkyl)chromones with 4-alkyl-3-cyanocoumarins

Abstract

2-(Polyfluoroalkyl)chromones react with 4-alkyl-3-cyanocoumarins in dichloromethane in the presence of triethylamine to give a wide variety of functionalized benzo[c]coumarin derivatives in good yields.

Ethyl 10-cyano-7-hydroxy-6-oxo-3-phenyl-8,9,10,10a-tetrahydro-6H-benzo[c]chromene-10-carboxylate

“…From a Cambridge Structural Database search (Groom et al, 2016), we found compounds identified by refcodes OKEYUB (Xiao et al, 2021), QABVEY (Wang et al, 2021), ALTENU (McPhail et al, 1973), AMUYIS (Alzaydi et al, 2016), ANOVEG (Sosnovskikh et al, 2016), ANOVIK (Sosnovskikh et al, 2016), BUWJEK (Parveen et al, 2015), BUXLOW (Fatunsin et al, 2010), DIPTUR (Casiraghi et al, 1986), DISJAS (Lee et al, 2013), SEDFEN (Appel et al, 2006), SIVQIZ (Poudel & Lee, 2014), SIJZER (Hussain et al, 2007), TUPJOE (Siegel et al, 2010), ZAQHIK (Dasari et al, 2012) and IZACIY (Duan et al, 2021) to be similar to the title compound.…”

Synthesis and Biological Properties of Coumarin Derivatives. A Review

“…From commercially available 4-hydroxycoumarin, Zhang et al [86] In the presence of phosphorous oxychloride as cyclizing agent, the cyclocondensation reaction of 2-oxo-2H-chromene-3-carboxylic acid and 4-amino-5-hydrazinyl-4H-[1,2,4]-triazole-3-thiol led to coumarin-substituted fused [1,2,4] 3,4]thiadiazole derivatives, Scheme 60. [87] Talhi et al [88] synthesized hydroxylated polyfunctionalized benzo[c]coumarins by a tandem pathway in one-pot conditions involving unprotected monohydroxy-3-(acetoacetyl)coumarin as an active methylene Michael donor with 4-oxo-4H-chromene-3-carboxylic acid as a Michael acceptor in the presence of a catalytic amount of 4-pyrrolidin-1-ylpyridine, Scheme 61.…”

“…Talhi et al [88] . synthesized hydroxylated polyfunctionalized benzo[c]coumarins by a tandem pathway in one‐pot conditions involving unprotected monohydroxy‐3‐(acetoacetyl)coumarin as an active methylene Michael donor with 4‐oxo‐4 H ‐chromene‐3‐carboxylic acid as a Michael acceptor in the presence of a catalytic amount of 4‐pyrrolidin‐1‐ylpyridine, Scheme 61.…”

Silver-catalysed three-component reactions of alkynyl aryl ketones, element selenium, and boronic acids leading to 3-organoselenylchromones

“…Despite the existence of a large number of synthetic approaches to functionalized chromone derivatives, 16 methods to access selenofunctionalized chromones have been less reported. A general approach for the construction of 3-organoselenylchromone is the direct introduction of selenium at the 3-position of the chromone backbone through a selenofunctionalization reaction, using diselenide, 17 sodium seleninate, 18 KSeCN, 19 and selenium dioxide 20 as the selenium source.…”