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Reactions of N ‐heteroarylformamide oximes and N ‐heteroarylacetamide oximes with N,N ‐dimethylformamide dimethyl acetal. Synthesis of 2‐methyl‐ s ‐triazolo[1,5‐ x ]azines and N ‐methylcyanoaminoazines
Author(s) -
Stanovnik Branko,
Štimac Anton,
Tišler Miha,
Verček Bojan
Publication year - 1982
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.5570190325
Subject(s) - chemistry , acetal , dimethylformamide , medicinal chemistry , oxime , organic chemistry , stereochemistry , solvent
N ‐Heteroarylformamide oximes 3 (R H) were converted with N,N ‐dimethylformamide dimethyl acetal (DMFDMA) into N ‐heteroaryl‐ N ‐methylcyanoamino compounds 5 , as the main products. In some instances N ‐heteroarylcyanoamino compounds 4 , cyanoimino compounds 7 , and some other products, such as 9 and 10 were also formed. On the other hand, N ‐heteroarylacetamide oximes 3 (R CH 3 ) were cyclized under the same reaction conditions into 2‐methyl‐ s ‐triazolo[1,5‐ x ]azines ( 6 ). N ‐Heteroarylacetamide O ‐methyl oximes 11 and 12 were prepared from the corresponding acetamidines 2 (R CH 3 ) and O ‐methylhydroxylamine.