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On triazoles XLVI . Synthesis of 1,3a,5,6,10c‐pentaazaacephenanthrylenes
Author(s) -
Berecz Gabor,
Párkányi László,
Reiter József,
Kálmán Alajos
Publication year - 2002
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.5570390415
Subject(s) - chemistry , alkyl , reactivity (psychology) , quinazoline , combinatorial chemistry , stereochemistry , organic chemistry , medicine , alternative medicine , pathology
A novel route to the synthesis of 6,7,8,9‐tetrahydro‐[1,2,4]triazolo[5,l‐ b ]quinazoline derivatives 4 through 5 and 6 was elaborated. During the synthesis of derivatives 6 novel type tetracyclic 2,3,7,8,9,10‐hexahydro‐1,3a,5,6,10c‐pentaazaacephenanthrylenes 9 were formed as by‐products. Their structure was proved by spec‐troscopic methods and by X‐ray diffraction spectra. There were also elaborated direct synthetic routes to derivatives 9 . Unexpectedly, the S ‐alkyl groups of derivatives 9 could be easily replaced by different amines, which is contrary to all our previous results. Possible explanations to this enhanced reactivity are given.