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Synthesis and reactions of tetrazolo[1,5‐α]pyrimidines
Author(s) -
Kappe Thomas,
Roschger Peter,
Färber Gerald
Publication year - 1993
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.5570300516
Subject(s) - chemistry , bromine , tetrazole , triethylamine , sulfuryl chloride , decarboxylation , acetic anhydride , oxazole , organic chemistry , acetic acid , medicinal chemistry , pyridine , derivative (finance) , catalysis , financial economics , economics
The reaction of “magic malonates” (bis‐2,4,6‐trichlorophenyl malonates, 1 ) with 5‐aminotetrazole ( 2 ) in the presence of triethylamine yields the ammonium salts 3 . Upon treatment of 3 with strong acids compounds 4a‐d were obtained as a mixture of isomeric tetrazolopyrimidines ( A ) and 2‐azidopyrimidines ( B ). Reaction of 4d with bromine or sulfuryl chloride leads by ring opening and decarboxylation to the halogenated tetrazole derivatives 5 or 7 , respectively. The action of acetic anhydride in pyridine on 3d yields the zwitterionic tetra‐mic acid derivative 10.