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1,2,4‐Triazolo[4,3‐ c ]pyrimidines from 4‐acylhydrazinopyrimidines
Author(s) -
Cocco Maria Teresa,
Congiu Cenzo,
Maccioni Antonio,
Onnis Valentina
Publication year - 1992
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.5570290549
Subject(s) - chemistry , cyanamide , dimethyl sulfoxide , pyrimidine , toluene , potassium carbonate , methylene , medicinal chemistry , sulfoxide , potassium , organic chemistry , stereochemistry
Abstract The reaction of N 1 ‐acetylacetamidrazones 1 with N ‐[bis(methylthio)methylene]cyanamide (2) at room temperature in the presence of potassium carbonate in dimethyl sulfoxide affords good yields of ethyl 4‐acylhydrazino‐2‐amino‐6‐methylthio‐5‐pyrimidine carboxylate 3 . By briefly refluxing compounds 3 in dimethyl sulfoxide, 1,2,4‐triazolo[4,3‐ c ]pyrimidine derivatives 4 were obtained. When equimolecular amounts of N 1 ‐acylacetamidrazones and compounds 2 were refluxed in dimethyl sulfoxide/toluene, compounds 4 were obtained directly.