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1,2‐Methyl shift in the reaction of 4,7‐dihydro‐4,5‐dimethyl‐7‐phenyl‐(1,2,4)‐triazolo[1,5‐ a ]pyrimidine with tosyl azide
Author(s) -
Komykhov Sergey A.,
Desenko Sergey M.,
Kaganovsky Alexander S.,
Orlov Valery D.,
Meier Herbert
Publication year - 2000
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570370135
Subject(s) - chemistry , enamine , adduct , azide , pyrimidine , tosyl , derivative (finance) , medicinal chemistry , organic chemistry , stereochemistry , catalysis , financial economics , economics
The reaction of the heterocyclic enamine 1 with tosyl azide ( 2 ) leads to the tosylimino derivative 4 of 1,2,4‐triazolo[1,5‐a]pyrimidine. The extrusion of nitrogen from the primary adduct 3 is followed by a 1,2‐shift of a methyl group. The structure determination of 4 is based on 1 H and 13 C nmr spectra including NOE measurements.