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Synthesis of acenaphtho[1,2‐ x ]heterocycles and spiro[acenaphthylene 1‐isoxazoles]
Author(s) -
Lefkaditis D. A.,
Nicolaides D. N.,
Papageorgiou G. K.,
StephanidouStephanatou J.
Publication year - 1990
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.5570270221
Subject(s) - chemistry , acenaphthylene , hydroxylamine hydrochloride , derivative (finance) , medicinal chemistry , ylide , hydrazine (antidepressant) , pyridazine , oxime , hydrate , hydroxylamine , nitrone , organic chemistry , cycloaddition , naphthalene , chromatography , financial economics , economics , catalysis
Methyl (Z)‐(1,2‐dihydro‐2‐oxo‐1‐acenaphthylenylidene)acetate 1 gives with hydroxylamine the oximes 2 and the pyrrole derivative 4 , whereas with hydrazines affords the pyridazinones 5 and 6 . A pyridazine derivative 8 is also isolated from the reaction of (1,2‐dihydro‐2‐oxo‐1‐acenaphthylenylidene)acetone 7 with hydrazine hydrate. Reaction between the spiro‐derivative 9 and hydroxylamine hydrochloride gives oxime 10 , whereas Wittig olefination of 9 with ylide 11 yields compound 12 which by reaction with 2,4,6‐trimethylbenzonitrile oxide ( 13 ) affords the dispiro‐derivatives 14 . Finally from the reaction of acenaphthylene‐1,2‐quinone ( 17 ) with the bisylide 16 the acenaphtho[1,2‐ c ]thiophene ( 18 ) is formed.