One-pot assembling of selenazolines from elemental selenium, alkenes and acetonitrile

被引：7

作者：

Kurkutov, Evgeny O. ^{[1
]}

Shainyan, Bagrat A. ^{[1
]}

机构：

[1] Siberian Branch Russian Acad Sci, AE Favorsky Irkutsk Inst Chem, Irkutsk 664033, Russia

来源：

MENDELEEV COMMUNICATIONS | 2022年 / 32卷 / 03期

关键词：

Keywords; selenium; organoselenium compounds; alkenes; acetonitrile; iodine assistance; solvent interception; 3-selenazolines;

D O I：

10.1016/j.mencom.2022.05.035

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new method for assembling 1,3-selenazolines by the iodine mediated reaction of the simplest building blocks such as elemental selenium, alkenes and acetonitrile has been discovered. A proposed mechanism includes the addition of the intermediate selenium iodides to alkene with subsequent solvent interception by the formed seleniranium ion.

引用

页码：395 / 396

页数：2

共 12 条

[1] Solvent interception, heterocyclization and desilylation upon NBS-induced sulfamidation of trimethyl(vinyl)silane [J].

Astakhova, Vera V. ;

Moskalik, Mikhail Yu. ;

Shainyan, Bagrat A. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (34) :7927-7937

[2] Synthesis of 1,3-selenazolies and bis(selenazoles) from primary selenocarboxylic amides and selenourea [J].

Geisler, K ;

Pfeiffer, WD ;

Künzler, A ;

Below, H ;

Bulka, E ;

Langer, P .

SYNTHESIS-STUTTGART, 2004, (06) :875-884

[3] SPECTROSCOPIC EVIDENCE FOR SELENIUM IODIDES IN CS2 SOLUTION - SE3I2, SE2I2, AND SEI2 [J].

GOPAL, M ;

MILNE, J .

INORGANIC CHEMISTRY, 1992, 31 (22) :4530-4533

[4] SULFUR AND SELENIUM IODINE COMPOUNDS - FROM NONEXISTENCE TO SIGNIFICANCE [J].

KLAPOTKE, T ;

PASSMORE, J .

ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (07) :234-240

[5] Preparation of 4,5-dihydro-1,3-selenazoles by reaction of aromatic primary selenoamides with acetylenedicarboxylate [J].

Koketsu, Mamoru ;

Sasaki, Tomomi ;

Ando, Hiromune ;

Ishihara, Hideharu .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2007, 44 (01) :231-232

[6] The iodine-assisted hydroxyselenenylation of alkenes with elemental selenium [J].

Kurkutov, Evgeny O. ;

Borodina, Tatyana N. .

MENDELEEV COMMUNICATIONS, 2020, 30 (06) :760-761

[7] Solvent nucleophilicity [J].

Minegishi, S ;

Kobayashi, S ;

Mayr, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (16) :5174-5181

[8] Oxidant effect, skeletal rearrangements and solvent interception in oxidative triflamidation of norbornene and 2,5-norbornadiene [J].

Moskalik, Mikhail Yu ;

Shainyan, Bagrat A. ;

Ushakov, Igor A. ;

Sterkhova, Irina, V ;

Astakhova, Vera V. .

TETRAHEDRON, 2020, 76 (11)

[9] Chemistry of biologically important synthetic organoselenium compounds [J].

Mugesh, G ;

du Mont, WW ;

Sies, H .

CHEMICAL REVIEWS, 2001, 101 (07) :2125-2179

[10] Method to build 2,4-substituted selenazole from β-azido diselenide and carboxylic acid: A formal synthesis of selenazofurin [J].

Qiao, Junfei ;

Liu, Yi ;

Du, Yuguo .

TETRAHEDRON, 2018, 74 (24) :3061-3068

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