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

ABSTRACT: 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.

SUBMITTER: Savych O

PROVIDER: S-EPMC7297054 | biostudies-literature | 2019 Sep

REPOSITORIES: biostudies-literature

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

Savych Olena O Kuchkovska Yuliya O YO Bogolyubsky Andrey V AV Konovets Anzhelika I AI Gubina Kateryna E KE Pipko Sergey E SE Zhemera Anton V AV Grishchenko Alexander V AV Khomenko Dmytro N DN Brovarets Volodymyr S VS Doroschuk Roman R Moroz Yurii S YS Grygorenko Oleksandr O OO

ACS combinatorial science 20190829 9

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 acc ...[more]

PMID: 31437394

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