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A simple one pot synthesis of condensed 1,2,4‐triazines by using the tandem a N‐ S N ipso and S N H ‐S N ipsa reactions
Author(s) -
Chupakhin Oleg N.,
Rusinov Gennady L.,
Beresnev Dmitry G.,
Charushin Valery N.,
Neunhoeffer Hans
Publication year - 2001
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.5570380414
Subject(s) - chemistry , nucleophile , bifunctional , tandem , ring (chemistry) , medicinal chemistry , triazine , salt (chemistry) , organic chemistry , materials science , composite material , catalysis
A new synthetic approach to condensed 1,2,4‐triazines based on using the tandem A N ‐S N ipso and S N H ‐S N ipso reactions has been developed. 5‐Methoxy‐3‐penyl‐1,2,4‐triazine and its N 1 ‐methyl quaternary salt were found to react with C,N‐, C,O‐ and N,N' ‐bifunctional nucleophiles ( m ‐phenylenediamine, resor‐cinol, semicarbazide and ureas) into triazacarbazoles, benzofuro[2,3‐ e ][1,2,4]‐triazines, and 6‐azapurine derivatives. In all cases nucleophiles attack first the unsubstituted C‐6 carbon of the triazine ring, while the final stage is replacement of the methoxy group affording cyclization products.