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Pseudo‐Seven‐Component Double Azido‐Ugi Reaction: an Efficient Synthesis of Bistetrazole Derivatives
Author(s) -
Kutovaya Irina V.,
Zarezin Danil P.,
Shmatova Olga I.,
Nenajdenko Valentine G.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900662
Subject(s) - tetrazole , isocyanide , chemistry , ugi reaction , combinatorial chemistry , ring (chemistry) , reaction conditions , component (thermodynamics) , catalysis , organic chemistry , physics , thermodynamics
Pseudo‐seven‐component double azido‐Ugi reactions were used for the synthesis of compounds bearing two 1,5‐disubstituted tetrazole rings in the structure. The influence of different inputs (amines, carbonyls, isocyanides) on the course of the reaction was studied. The method opened an efficient pathway to the construction of compounds having two tetrazole rings in the structure. Target compounds can be prepared from easily available starting materials. In the case of the azido‐Ugi reaction with benzyl isocyanide, the prepared N‐substituted bistetrazoles can be efficiently debenzylated under catalytic hydrogenation conditions to form the corresponding NH‐tetrazoles in quantitative yields.