An advanced and novel one-pot synthetic method for diverse benzo[c]chromen-6-ones by transition-metal free mild base-promoted domino reactions of substituted 2-hydroxychalcones with β-ketoesters and its application to polysubstituted terphenyls

Abstract

Novel and efficient one-pot syntheses of a variety of benzo[c]chromen-6-one derivatives were accomplished using Cs2CO3-promoted reactions between substituted 2-hydroxychalcones and β-ketoesters. These reactions involved domino Michael addition/intramolecular aldol/oxidative aromatization/lactonization and provided a rapid synthetic route for the production of biologically interesting novel benzo[c]chromen-6-one molecules bearing several different substituents on benzene rings. As an application of this methodology, several synthesized benzo[c]chromen-6-ones were transformed into highly functionalized novel terphenyls.

DMAP-Catalyzed Reaction of Diethyl 1,3-Acetonedicarboxylate with 2-Hydroxybenzylideneindenediones: Facile Synthesis of Fluorenone-Fused Coumarins

“…Although the crude NMR spectrum indicated that 2,4-dihydroxybenzylideneindenedione managed to yield the desired coumarin 5k, the compound was tedious to purify. Based on our findings and the literature, 30…”

“…28 The base-mediated reactions of diethyl 1,3-acetonedicarboxylate with 2-hydroxychalcones have been employed in the synthesis of benzene fused coumarins (Scheme 1). [29][30][31] O OMe However, the reaction of substituted -keto esters with 2-(2-hydroxybenzylidene) of both cyclic and acyclic 1,3-dicarbonyl compounds have never been studied. This type of reactions could provide a template for the synthesis of a wide variety of new fused coumarins.…”

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.…”

Recent Progress in Transition‐Metal‐Free, Base‐Mediated Benzannulation Reactions for the Synthesis of a Diverse Range of Aromatic and Heteroaromatic Compounds

“…Similarly, we investigated a new and efficient method for the synthesis of biologically interesting benzo[ c ]chromen‐6‐one derivatives 26 from readily available substituted 2‐hydroxychalcones 24 and β‐ketoesters 25 through tandem Michael addition/intramolecular aldol/aromatization/lactonization reactions by using two equivalents of Cs 2 CO 3 (Scheme ) . The synthetic utility of this method was demonstrated by the conversion of benzo[ c ]chromen‐6‐one derivatives into pharmaceutically important terphenyls ( 27 ) in good yields by using MeI in the presence of KOH in wet DMSO at room temperature.…”