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Potential Non-Steroidal Estrogens and Antiestrogens, I Synthesis of Some 7 -Methoxy-2-(1H)-quinolone Derivatives

Fatma A. A. El-Mariah ; Chemistry Department, University College jor Girls, Ain-Shams University, Heliopolis, Cairo, A. R. Egypt
Thomas Kappe ; Institut fur Organische Chemie, Karl-Franzens-Universitat, Graz, Austria

Sažetak

Reaction of 4-hydroxy-7-methoxy-2(lH)-quinolone (1) with
iodosobenzenes, prepared in situ from the dichloroiodo compounds
2a,b, afforded the iodoniumylides 3a,b in good yields. Their thermal
rearrangement produced the 3-iodo-4-aryloxy-quinolones 4a,b.
Reductive -deiodinatton of 4a,b gave the corresponding arylethers
5a,b. By photocyclization 4a as well as 5a yielded the benzofuro-
-quinolone 6a (4b or 5b could not be cyclized to 6b). Acid catalyzed
»transylidation« of the iodonium-ylides 3a,b with triphenylphosphane,
pyridine and isoquinoline as nucleophiles produced the
corresponding P- and N-ylides 8, 9a,b, respectively. The pyridinium-
(9a) and isoquinolinium-ylid (9b) were also prepared from
the 3-chloro-4-hydroxy-2-quinolone 7a, which in turn could be
obtained by the action of hydrochloric acid on 3a,b (7b was obtained
by careful reaction of HBr with 3a).

Ključne riječi

Hrčak ID:

177586

URI

https://hrcak.srce.hr/177586

Datum izdavanja:

16.5.1986.

Posjeta: 890 *