Peroxidation of 3,4-dihydro-1,4-benzoxazin-2-ones

被引：18

作者：

Wang, Jie ^{[1
]}

Bao, Xiazhen ^{[1
]}

Wang, Jiayuan ^{[1
]}

Huo, Congde ^{[1
]}

机构：

[1] Northwest Normal Univ, Coll Chem & Chem Engn, Gansu Int Sci & Technol Cooperat Base Water Reten, Lanzhou 730070, Gansu, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2020年 / 56卷 / 27期

基金：

中国国家自然科学基金;

关键词：

CATALYZED PEROXIDATION; TERT; FUNCTIONALIZATION; ARTEMISININ; QINGHAOSU;

D O I：

10.1039/c9cc09778c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The sp(3)-C-H peroxidation of 3,4-dihydro-1,4-benzoxazin-2-ones was achieved under mild and simple catalyst-free reaction conditions. A range of biologically important alkylated benzoxazinone peroxides are synthesized in high yield with a good functional group tolerance. The C(sp(3))-OO bond was constructed efficiently and could be further converted into C(sp(3))-C(sp(3)), C(sp(3))-C(sp(2)), C(sp(3))-C(sp), C-P and C=O bonds by late-stage functional group transformations.

引用

页码：3895 / 3898

页数：4

共 50 条

[1] Perspectives on 1,4-benzodioxins, 1,4-benzoxazines and their 2,3-dihydro derivatives [J].

Achari, B ;

Mandal, SB ;

Dutta, PK ;

Chowdhury, C .

SYNLETT, 2004, (14) :2449-2467

[2] REACTIONS OF 19-ETHOXYCARBONYL-19-DEMETHYLVINCADIFFORMINE - SYNTHESIS OF 19-ETHOXYCARBONYL-19-DEMETHYLAPOVINCAMINE [J].

BELATTAR, A ;

SAXTON, JE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (13) :1583-1585

[3] Novel synthesis of 3,4-dihydro-5-bromo[1,4]oxazin-2-one derivatives, new protease inhibitor scaffold [J].

Bihel, F ;

Kraus, JL .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (05) :793-799

[4] Kharasch reaction: Cu-catalyzed and non-Kharasch metal-free peroxidation of barbituric acids [J].

Bityukov, Oleg V. ;

Vil', Vera A. ;

Sazonov, George K. ;

Kirillov, Andrey S. ;

Lukashin, Nikita V. ;

Nikishin, Gennady I. ;

Terent'ev, Alexander O. .

TETRAHEDRON LETTERS, 2019, 60 (13) :920-924

[5] CONCISE SYNTHESIS OF YINGZHAOSU-C AND EPI-YINGZHAOSU-C BY PEROXYL RADICAL CYCLIZATION - ASSIGNMENT OF RELATIVE CONFIGURATION [J].

BOUKOUVALAS, J ;

POULIOT, R ;

FRECHETTE, Y .

TETRAHEDRON LETTERS, 1995, 36 (24) :4167-4170

[6] ACID-CATALYZED DEHYDRATION OF NAPHTHALENE HYDRATES [J].

BOYD, DR ;

MCMORDIE, RAS ;

SHARMA, ND ;

OFERRALL, RAM ;

KELLY, SC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (21) :7822-7823

[7] ALKALOID STUDIES .46. ALKALOIDS OF ASPIDOSPERMA OBSCURINERVIUM AZEMBUJA - NEW CLASS OF HEPTACYCLIC INDOLE ALKALOIDS [J].

BROWN, KS ;

DJERASSI, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (12) :2451-&

[8] Synthesis and in vitro Trichomonacidal activities of some new dialkylperoxides and 1,2,4-trioxanes [J].

Camuzat-Dedenis, B ;

Provot, O ;

Cointeaux, L ;

Perroux, V ;

Berrien, JF ;

Bories, C ;

Loiseau, PM ;

Mayrargue, JL .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2001, 36 (10) :837-842

[9] The Rearrangement of Peroxides for the Construction of Fluorophoric 1,4-Benzoxazin-3-one Derivatives [J].

Chaudhari, Moreshwar B. ;

Chaudhary, Atul ;

Kumar, Vishnupriya ;

Gnanaprakasam, Boopathy .

ORGANIC LETTERS, 2019, 21 (06) :1617-1621

[10] Iron-Catalyzed Batch/Continuous Flow C-H Functionalization Module for the Synthesis of Anticancer Peroxides [J].

Chaudhari, Moreshwar B. ;

Moorthy, Suresh ;

Patil, Sohan ;

Bisht, Girish Singh ;

Mohamed, Haneef ;

Basu, Sudipta ;

Gnanaprakasam, Boopathy .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (03) :1358-1368

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