One-Pot Parallel Synthesis of 5-(Dialkylamino)tetrazoles

被引：6

作者：

Savych, Olena ^{[1
,2
]}

Kuchkovska, Yuliya O. ^{[1
,3
]}

Bogolyubsky, Andrey V. ^{[1
]}

Konovets, Anzhelika I. ^{[1
]}

Gubina, Kateryna E. ^{[3
]}

Pipko, Sergey E. ^{[4
]}

Zhemera, Anton V. ^{[1
]}

Grishchenko, Alexander V. ^{[1
]}

Khomenko, Dmytro N. ^{[3
]}

Brovarets, Volodymsyr S. ^{[2
]}

Doroschuk, Roman ^{[3
]}

Moroz, Yurii S. ^{[3
,4
]}

Grygorenko, Oleksandr O. ^{[1
,3
]}

机构：

[1] Enamine Ltd, Chervonotkatska St 78, UA-02094 Kiev, Ukraine

[2] Natl Acad Sci Ukraine, VP Kukhar Inst Bioorgan Chem & Petrochem, Murmanska St 1, UA-02094 Kiev, Ukraine

[3] Taras Shevchenko Natl Univ Kyiv, Volodymyrska St 60, UA-01601 Kiev, Ukraine

[4] Chemspace, Ilukstes Iela 38-5, LV-1082 Riga, Latvia

来源：

ACS COMBINATORIAL SCIENCE | 2019年 / 21卷 / 09期

关键词：

tetrazoles; 2,2,2-trifluoroethylthiocarbamate; thiourea; heterocyclization; REAL (readily accessible) compounds; ANTIBACTERIAL ACTIVITY; MEDICINAL CHEMISTRY; TETRAZOLES; 5-AMINOTETRAZOLES; DIVERSITY;

D O I：

10.1021/acscombsci.9b00120

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Two protocols for the combinatorial synthesis of 5-(dialkylamino)tetrazoles were developed. The best success rate (67%) was shown by the method that used primary and secondary amines, 2,2,2-trifluoroethylthiocarbamate, and sodium azide as the starting reagents. The key steps included the formation of unsymmetrical thiourea, subsequent alkylation with 1,3-propane sultone and cyclization with azide anion. A 559-member aminotetrazole library was synthesized by this approach; the overall readily accessible (REAL) chemical space covered by the method exceeded 7 million feasible compounds.

引用

页码：635 / 642

页数：8

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