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Convenient synthesis of fused heterocycles from α‐ketohydroximoyl chlorides and heterocyclic amines
Author(s) -
PÁrkÁnyi Cyril,
Abdelhamid Abdou O.,
Cheng John C. S.,
Shawali Ahmad S.
Publication year - 1984
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.5570210421
Subject(s) - chemistry , pyrazine , pyridine , aminopyridines , 1,2,4 triazole , pyrimidine , pyrazole , medicinal chemistry , triazole , combinatorial chemistry , stereochemistry , organic chemistry
Nitroso derivatives of imidazo[1,2‐ a ]pyridine ( 11, 13, 14 ), imidazo[1,2‐ a ]pyrimidine ( 15 ), imidazo[1,2‐ a ]pyrazine ( 16 ), imidazo[1,2‐ b ]pyrazole ( 17 ), and imidazo[1,2‐ b ]‐1,2,4‐triazole ( 19 ) were obtained in good yields from α‐ketohydroximoyl chlorides 3 and 2‐aminopyridines ( 4–6 ), 2‐aminopyrimidine ( 7 ), 2‐aminopyrazine ( 8 ), 5‐amino‐3‐phenylpyrazole ( 9 ), and 3‐amino‐2 H ‐1,2,4‐triazole ( 10 ), respectively. Under different conditions, the reaction of 3 with 3‐amino‐2 H ‐1,2,4‐triazole ( 10 ) and 2‐aminopyrazine ( 8 ) afforded the noncyclized substitution products 18 and 22 , respectively. The structures of the products were assigned and confirmed on the basis of their elemental analyses, spectral data, and alternate synthesis wherever possible.