One-Pot Four-Component Assembling for Selenoureas

被引：11

作者：

Li, Lai ^{[1
]}

Wu, Jiaqi ^{[1
]}

Wei, Linsha ^{[1
]}

Lu, Jianmei ^{[1
]}

Jiang, Xuefeng ^{[2
]}

机构：

[1] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Zhejiang, Peoples R China

[2] East China Normal Univ, Sch Chem & Mol Engn, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 01期

关键词：

BIOLOGICAL APPLICATIONS; BICYCLIC DERIVATIVES; EFFICIENT SYNTHESIS; SELENIUM; CHEMISTRY; 1,3-SELENAZINE; ANTIOXIDANT; THIOUREAS; ANALOGS; REAGENT;

D O I：

10.1021/acs.joc.0c02179

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and practical method for the straightforward construction of unsymmetrical selenoureas and cycloselenoureas via the combination of selenium powder, chloroform, and two different amines was comprehensively achieved in one-pot with only the assistance of a base under mild conditions. Thirty-three new structures of unsymmetrical selenoureas including three chiral examples and eight cycloselenoureas were achieved. 1,1-Dimethyl-3-phenylselenourea II, which shows good fungicidal activity, was practically synthesized through this protocol in gram-scale. Isoselenocyanate was further confirmed as a key intermediate by control experiment.

引用

页码：446 / 454

页数：9

共 52 条

[1] Discovery of New Selenoureido Analogues of 4-(4-Fluorophenylureido)benzenesulfonamide as Carbonic Anhydrase Inhibitors [J].

Angeli, Andrea ;

Tanini, Damiano ;

Peat, Thomas S. ;

Mannelli, Lorenzo Di Cesare ;

Bartolucci, Gianluca ;

Capperucci, Antonella ;

Ghelardini, Carla ;

Supuran, Claudiu T. ;

Carta, Fabrizio .

ACS MEDICINAL CHEMISTRY LETTERS, 2017, 8 (09) :963-968

[2] Synthesis of novel acyl selenoureido benzensulfonamides as carbonic anhydrase I, II, VII and IX inhibitors [J].

Angeli, Andrea ;

Carta, Fabrizio ;

Bartolucci, Gianluca ;

Supuran, Claudiu T. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2017, 25 (13) :3567-3573

[3]

[Anonymous], SADABS

[4]

[Anonymous], 2018, SHELXTL

[5] Selenocarbonyl synthesis using Woollins reagent [J].

Bhatacharyya, P ;

Woollins, JD .

TETRAHEDRON LETTERS, 2001, 42 (34) :5949-5951

[6] New Bicyclic 1,3-Selenazine Derivatives: Distribution in Model Biological Media and Membrane Permeability [J].

Blokhina, Svetlana V. ;

Volkova, Tatyana V. ;

Ol'khovich, Marina V. ;

Sharapova, Angelica V. ;

Proshin, Alexey N. ;

Perlovich, German L. .

JOURNAL OF CHEMICAL AND ENGINEERING DATA, 2015, 60 (04) :1146-1152

[7] Solubility and Solution Thermodynamics of Novel Bicyclic Derivatives of 1,3-Selenazine in Biological Relevant Solvents [J].

Blokhina, Svetlana V. ;

Volkova, Tatyana V. ;

Ol'khovich, Marina V. ;

Sharapova, Angelika V. ;

Proshin, Alexey N. ;

Perlovich, German L. .

JOURNAL OF CHEMICAL AND ENGINEERING DATA, 2014, 59 (07) :2298-2304

[8] Synthesis and Leishmanicidal Activity of Novel Urea, Thiourea, and Selenourea Derivatives of Diselenides [J].

Diaz, Marta ;

de Lucio, Hector ;

Moreno, Esther ;

Espuelas, Socorro ;

Aydillo, Carlos ;

Jimenez-Ruiz, Antonio ;

Angel Toro, Miguel ;

Jesus Gutierrez, Killian ;

Martinez-Merino, Victor ;

Cornejo, Alfonso ;

Antonio Palop, Juan ;

Sanmartin, Carmen ;

Plano, Daniel .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2019, 63 (05)

[9] Copper(I)-catalyzed highly efficient synthesis of benzoselenazoles and benzotellurazoles [J].

Fujiwara, Shin-ichi ;

Asanuma, Yoshiaki ;

Shin-ike, Tsutomu ;

Kambe, Nobuaki .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (21) :8087-8090

[10]

Garnica P, 2018, ACS MED CHEM LETT, V9, P306, DOI [10.1021/acsmedchemiett.7b00482, 10.1021/acsmedchemlett.7b00482]

← 1 2 3 4 5 6 →