Two versatile routes towards Cerpegin and analogues: applications of a one pot reaction to new analogues of Cerpegin

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“…Similarly, diazonium salt (2) was easily coupled with ethyl cyanoacetate to give 2- In this study, the reactivity of the enaminonitrile moiety in compound (1) was investigated aiming to annulate the fused pyrimidine analogues. As follows, the enaminonitrile derivative The recorded mass spectrum at m/z 429.00 corresponds to the formula C23H19N5O2S, besides its ( 1 H NMR) at δ 2.58 (s, 3H, CH3) further supported the formation of methylthio derivative (12). The synthetic efficiency of the methylthio compound (12) was scrutinized in this work.…”

“…As follows, the enaminonitrile derivative The recorded mass spectrum at m/z 429.00 corresponds to the formula C23H19N5O2S, besides its ( 1 H NMR) at δ 2.58 (s, 3H, CH3) further supported the formation of methylthio derivative (12). The synthetic efficiency of the methylthio compound (12) was scrutinized in this work.…”

“…Pyrimidine (1,3diazine), an essential nucleus in DNA and RNA, was found to have wide spectrum of biological activities [7]. Pyrimidine derivatives have gained interest in the field of drug research since they exhibited a broad range of biological activities including antimicrobial [8], antitumor [9], bronchodilator [10], antihistaminic [11], antihypersentensive [12], anti-psoriasis [13] and antipyretic [14] activity. Besides, the pyridopyrimidine are a critical class of annulated uracils with biological importance due to their linking with the purine and pyridine system [15].…”

Cerpegin-derived furo[3,4-c]pyridine-3,4(1H,5H)-diones enhance cellular response to interferons by de novo pyrimidine biosynthesis inhibition

“…The general procedure used for the synthesis of substituted cerpegin analogs was described in our previous reports [43,45]. Initial (E)-ethyl 4-(2-(dimethylamino)vinyl)-5,5disubstituted-2-oxo-2,5-dihydrofuran-3-carboxylates (II) were synthesized according to previously described methods [43][44][45][46]. Briefly, condensation of 2-oxo-2,5-dihydrofurans (I; 10 mmol) and DMF/DMA (1.44 ml; 12 mmol) was achieved in 3 h in boiling anhydrous xylene (10 ml) to give the corresponding compounds (II) in yields of up to 80-90% (Scheme 1).…”

Synthesis of Annulated and Spirocyclic Butenolide Derivatives by Condensation of Malonates with Cyclic α-Hydroxy β-Dicarbonyl Compounds

“…Such a structural motif could be accessible by vinylogization of an α-hydroxy ketone 5 (acyloin) by aldol (or Knoevenagel if R 1 is an electron-withdrawing group) condensation with an enolate derived from carboxylic acid derivative 4. 4 Since we had recently discovered a simple access to acyloins by cerium-catalyzed, aerobic α-hydroxylation of β-oxoesters, 5 we considered these products to be perfect 1,2-dioxy-functionalized building blocks for the construction of butenolide derivative rings by cyclocondensation with malonates. Scheme 1 Strigol (1) and Carlactone (2), two naturally occurring strigolactones, and a retrosynthetic approach to butenolides 3…”