New Preparation of 1,2,4,5‐Tetraoxanes.

Abstract

Other 6-membered heterocycles R 0670New Preparation of 1,2,4,5-Tetraoxanes. -A new convenient synthesis of spirocyclic tetraoxanes is presented, involving the reaction of gem-bis(hydroperoxy)cycloalkanes, e.g. (I), with acetals or ketals catalyzed by BF3·OEt2. A wide range of acetals of alicyclic and acyclic carbonyl compounds is tolerated. In most cases, a mixture of unsymmetrical and symmetrical tetraoxanes is obtained, the latter by bis (hydroperoxide) dimerization. -(TERENT'EV, A. O.; KUTKIN, A. V.; STARIKOVA, Z. A.; ANTIPIN, M. Y.; OGIBIN*, Y. N.; NIKISHIN, G.

Synthesis and Antileishmanial Activity of 1,2,4,5-Tetraoxanes against Leishmania donovani

“…The structures of the 15 tetraoxanes assayed against intramacrophage amastigote forms of L. donovani differ only in the chemical nature of the cyclohexyl substituent (Table 1). From this library, only compounds L137 [40], LC140 [14], L153 [41], and LC163 [19] were previously reported in the context of antiparasitic chemotherapy (compound LC163 was disclosed by our group). For comparative purposes, we have also evaluated the activity of a small library of 1,2,4-trioxolanes and that of the known peroxide-based antiplasmodial drugs dihydroartemisinin (DHA) and artesunate (ATS) ( Table 1).…”

Mild and Efficient Strontium Chloride Hexahydrate-Catalyzed Conversion of Ketones and Aldehydes into Corresponding gem- Dihydroperoxides by Aqueous H2O2

“…In recent years, much research has been directed towards gem -dihydroperoxides (DHPs) [ 1 ], due to their importance as useful intermediates in the synthesis of various peroxides, including tetraoxanes [ 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 ], and their analogues such as silatetroxanes [ 10 ], spirobisperoxyketals [ 11 ], and tetroxycycloalkanes [ 12 ], and epoxidation of α,β-unsaturated ketones [ 13 ]. These compounds have also recently been utilized as effective reagents in: (i) oxidation of various compounds [ 14 ] such as sulfides [ 15 ], (ii) enantioselective oxidation of 2-substituted 1,4-naphthoquinones [ 16 ], and (iii) as initiators in polymerization reactions [ 17 , 18 ].…”

Two-Step Synthesis of Achiral Dispiro-1,2,4,5-tetraoxanes with Outstanding Antimalarial Activity, Low Toxicity, and High-Stability Profiles

“…There are many methods available for the synthesis of 1,2,4,5-tetraoxanes, and these reactions are highly dependent on substrate, temperature, concentration, pH, addition mode, solvent, and type of substrate. [15][16][17][18][19][20][21][22][23][24][25][26][27] Here, we present a two-step synthesis of a range of achiral dispiro 1,2,4,5-tetraoxanes with highly potent antimalarial activity. These compounds are rapidly synthesized from inexpensive, readily available starting materials.…”

“…They are achiral and easily prepared from inexpensive materials. There are many methods available for the synthesis of 1,2,4,5-tetraoxanes, and these reactions are highly dependent on substrate, temperature, concentration, pH, addition mode, solvent, and type of substrate. – …”