Powerful approach to synthesis of fused oxa-aza[3.3.3]propellanes via chemoselective sequential MCR in a single pot

Design, synthesis, and DNA interaction studies of furo-imidazo[3.3.3]propellane derivatives: Potential anticancer agents

“…Although, there are over 10,000 representatives of this chemical class, new propellanecontaining natural products still being discovered, with unique structures and activity profiles [1]. Several propellanes exhibiting antiviral [2], antifungal [3], antibiotic [4,5] and anticancer [6][7][8][9] activities have been previously described. For example, Dichrocephone B, that was isolated from Dichrocephala benthamii, contains a [3.3.3] propellane core structure fused to a unique oxetane ring ( Fig.…”

“…Several methods are reported for the synthesis of heterocylic [3.3.3]propellanes. Oxa-aza [3.3.3]propellanes were synthesized by Alizadeh et al [4,[22][23][24], Yavari et al [25], Chen et al [26] and Zhang et al [27]. Hassan et al reported the formation of oxaaza-and bisoxathia-aza [3.3.3]-propellanes via nucleophilic addition of symmetrical and unsymmetrical N 1 ,N 2 -disubstituted-1,2-dicarbothioamides on dicyanomethylene-1,3-indanedione 1 [28].…”

One-pot, sequential four-component synthesis of novel heterocyclic [3.3.3] propellane derivatives at room temperature

“…22, 23 Propellanes due to their challenging framework and broad spectra of biological and pharmacological activities, constitute an interesting class of compounds in organic chemistry.…”

“…Recently, there have been some reports about the synthesis of propellane compounds from ninhydrin [25][26][27][28][29][30][31][32] and acenaphthoquinone. [32][33][34] In continuation of our research on the synthesis of biologically important heterocycles and green chemistry protocols, [35][36][37][38][39][40][41][42][43][44][45][46][47] we report a simple and efficient method for the synthesis of novel propellane derivatives via a one-pot, sequential four-component condensation reaction between acenaphthoquinone (1), malono derivatives (2), primary amines (4) and b-ketoester or b-diketone (5) derivatives in the presence of triethylamine in ethanol at room temperature (Scheme 1).…”

Domino Knoevenagel Condensation/Aza‐Ene Addition/N‐Cyclization Route to Functionalized Imidazo[1,2‐a]pyridines and Pyrido[1,2‐a]pyrimidines

“…For instance, the reaction of heterocyclic ketene aminals with reagents that contain bis(electrophilic) groups such as 1,3‐dicarbonyl,10a 2‐(1,3‐dioxo‐1 H ‐indenylidene)malononitrile,10b benzylidenemalononitrile,10c 3‐methyl‐1‐phenyl‐1 H ‐pyrazol‐5(4 H )‐one,10d allene,10e β ‐oxodithioester,10f ethyl 4,4,4‐trifluorobut‐2‐ynoate,10g isatin,10h 4‐methyleneoxetan‐2‐one,10i and methyl vinyl ketone10j moieties have been investigated. However, reports of the syntheses of imidazo[1,2‐ a ]pyridines and pyrido[1,2‐ a ]pyrimidines that have a spirooxindole ring at the C‐7 and C‐8 positions, respectively, are limited 11.…”