1. One-Pot Parallel Synthesis of 5-(Dialkylamino)tetrazoles.
- Author
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Savych O, Kuchkovska YO, Bogolyubsky AV, Konovets AI, Gubina KE, Pipko SE, Zhemera AV, Grishchenko AV, Khomenko DN, Brovarets VS, Doroschuk R, Moroz YS, and Grygorenko OO
- Subjects
- Alkylation, Amines chemistry, Azides chemistry, Catalysis, Cyclization, Molecular Structure, Sodium Azide chemistry, Temperature, Thiocarbamates chemistry, Thiophenes chemistry, Thiourea chemistry, Tetrazoles chemical synthesis
- 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.
- Published
- 2019
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