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Synthesis, structure, and some chemical properties of diferrocenyl‐1,2,3‐triazines
Author(s) -
Klimova Elena I.,
Klimova Tatiana,
Álamo Marcos Flores,
Iturbide Daniel Méndez,
García Marcos Martínez
Publication year - 2009
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.93
Subject(s) - chemistry , sodium azide , yield (engineering) , alkyl , triazine , hydrolysis , tetrafluoroborate , azide , iodide , medicinal chemistry , organic chemistry , catalysis , ionic liquid , materials science , metallurgy
The reactions of 1‐amino‐2,3‐diferrocenylcyclopropenylium tetrafluoroborate ( 5a , 5b , 5c ) or 2,3‐diferrocenyl‐1‐methylthiocyclopropenylium iodide with sodium azide afford 5‐amino‐4,6‐diferrocenyl‐1,2,3‐triazines ( 7a , 7b , 7c ) or 5‐methylthio‐4,6‐diferrocenyl‐ and 4‐methylthio‐5,6‐diferrocenyl‐1,2,3‐triazines ( 8a and 8b ), respectively. Their structures were established using spectroscopic methods and that of compound 8a was confirmed using X‐ray diffraction analysis. Triazines 5a , 5b , 5c react with alkyl iodides to yield N(2)‐ and N‐alkyl‐C(5)‐derivatives. Their alkaline hydrolysis results in 2‐methyl‐4,6‐diferrocenyl‐2,5‐dihydro‐1,2,3‐triazin‐5‐one ( 16 ) and 4,6‐diferrocenyl‐5‐hydroxy‐1,2,3‐triazine ( 17 ). J. Heterocyclic Chem., 46, 477 (2009).