One-pot synthesis of 4H-Chromene and Dihydropyrano[3,2-c]chromene derivatives in hydroalcoholic media

Abstract

4H-Cromenos e diidropirano[3,2-c]cromenos são obtidos em rendimentos bons a excelentes através de um procedimento simples, brando e eficiente usando poli(N,N´-dibromo-N-etil-benzeno-1,3-dissulfonamida) [PBBS] e N,N,N´,N´-tetrabromobenzeno-1,3-dissulfonamida [TBBDA] como catalisadores. 4H-Chromenes and dihydropyrano[3,2-c]chromenes are obtained in good to excellent yields by a simple, mild and efficient procedure using poly(N,N'-dibromo-N-ethyl-benzene-1,3-disulfonamide) [PBBS] and N,N,N',N'-tetrabromobenzene-1,3-disulfonamide [TBBDA ] as catalysts.

Novel bis(dihydropyrano[3,2‐c]chromenes): Synthesis, Antiproliferative Effect and Molecular Docking Simulation

“…Previously, impressive endeavors have been made in the synthesis of pyrano[3,2-c] chromenes 4 as an important class of compounds. Several methods have been accounted for to the synthesis of this class of compounds, including the reaction of aromatic aldehydes 1, malononitrile 2, and 4-hydroxycoumarin 3 in the presence of homogeneous or heterogeneous catalysts under conventional heating, microwave irradiation, or ultrasound irradiation (Scheme 1) [25][26][27][28][29][30][31][32][33][34][35][36][37].…”

Theoretical and Experimental Approaches Aimed at Drug Design Targeting Neurodegenerative Diseases

“…Remarkably, docking analysis (on the basis of the binding energy calculation), predicted the activity of these compounds, showing that the most active molecule of this new series had the best energy score [19]. Other compounds like dyhidropyrano[c]chromene derivatives have been used as cognitive enhancers in the treatment of different NDD [38]. Diverse protocols of green chemistry have been adapted to obtain this scaffold.…”

“…Similarly, Majid and co-workers carried out an scheme involving the use of morpholine as a friendly organocatalyst and water as a solvent in the one-pot synthesis of dihydropyrano[c]chromene derivatives 33 ( Figure 8) [40]. Other compounds like dyhidropyrano[c]chromene derivatives have been used as cognitive enhancers in the treatment of different NDD [38]. Diverse protocols of green chemistry have been adapted to obtain this scaffold.…”

Reactions of salicylaldehyde and enolates or their equivalents: versatile synthetic routes to chromane derivatives

“…In another approach, Ghorbani-Vaghei and co-workers used a N , N , N ’, N ’-tetrabromobenzene-1,3-disulfonamide (TBBDA) mediated Knoevenagel reaction of salicylaldehyde ( 5 ) and two equivalents of malononitrile ( 20 ) or its derivative 29 to give the corresponding 2-aminochromene derivatives 22 and 37 in 92 and 82% yields respectively (Scheme 13) [26]. It is instructive to note that TBBDA is a versatile reagent in organic synthesis and has been reported to be efficient in oxidation of primary and secondary alcohols [27], in bromination of aromatic compounds [28], as catalytic reagents for silylation of alcohols, phenols, and thiols using hexamethyldisilazane [29], in conversion of urazoles to triazolinediones [30], and in oxidation of 1,3,5-trisubstituted pyrazolines [31].…”