Open AccessOne-Pot Parallel Synthesis of 5-(Dialkylamino)tetrazoles
Author(s) -
Olena Savych,
Yuliya O. Kuchkovska,
Andrey V. Bogolyubsky,
Anzhelika I. Konovets,
Kateryna E. Gubina,
Sergey E. Pipko,
Anton V. Zhemera,
A. V. Grishchenko,
Dmytro M. Khomenko,
В. С. Броварец,
Roman O. Doroschuk,
Yurii S. Moroz,
Oleksandr O. Grygorenko
Publication year - 2019
Publication title -
acs combinatorial science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.928
H-Index - 81
eISSN - 2156-8952
pISSN - 2156-8944
DOI - 10.1021/acscombsci.9b00120
Subject(s) - chemistry , thiourea , sodium azide , reagent , azide , alkylation , combinatorial chemistry , primary (astronomy) , organic chemistry , catalysis , physics , astronomy
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.