Synthesis of Non-symmetrical Dispiro-1,2,4,5-Tetraoxanes and Dispiro-1,2,4-Trioxanes Catalyzed by Silica Sulfuric Acid

被引：12

作者：

Amado, Patricia S. M. ^{[1
,2
,3
]}

Frija, Luis M. T. ^{[4
]}

Coelho, Jaime A. S. ^{[5
]}

O'Neill, Paul M. ^{[3
]}

Cristiano, Maria L. S. ^{[1
,2
]}

机构：

[1] Univ Algarve, Ctr Marine Sci CCMAR, P-8005039 Faro, Portugal

[2] Univ Algarve, FCT, Dept Chem & Pharm, P-8005039 Faro, Portugal

[3] Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England

[4] Univ Lisbon, Ctr Quim Estrutural CQE, Inst Super Tecn, P-1049001 Lisbon, Portugal

[5] Univ Lisbon, Fac Ciencias, Ctr Quim Estrutural CQE, P-1749016 Lisbon, Portugal

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 15期

关键词：

PLASMODIUM-FALCIPARUM; GEM-DIHYDROPEROXIDES; ARTEMETHER-LUMEFANTRINE; ARTEMISININ RESISTANCE; EFFICIENT; MALARIA; HYDROPEROXYSILYLATION; IDENTIFICATION; ENDOPEROXIDE; TETRAOXANES;

D O I：

10.1021/acs.joc.1c01258

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel protocol for the preparation of nonsymmetrical 1,2,4,5-tetraoxanes and 1,2,4-trioxanes, promoted by the heterogeneous silica sulfuric acid (SSA) catalyst, is reported. Different ketones react under mild conditions with gemdihydroperoxides or peroxysilyl alcohols/beta-hydroperoxy alcohols to generate the corresponding endoperoxides in good yields. Our mechanistic proposal, assisted by molecular orbital calculations, at the.B97XD/def2-TZVPP/PCM(DCM)// B3LYP/6-31G(d) level of theory, enhances the role of SSA in the cyclocondensation step. This novel procedure differs from previously reported methods by using readily available and inexpensive reagents, with recyclable properties, thereby establishing a valid alternative approach for the synthesis of new biologically active endoperoxides.

引用

页码：10608 / 10620

页数：13

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