The
principal aim of the presented work was to evaluate various but structure closely related classes of the chiral spiro-compounds for their cytostatic and antiviral
activities. For this reason S.
Raić-Malić et
al.50 synthesized and tested antiviral and antiviral activity of new
spiro compound indolinospirobenzopyrans
(93-95), indolinospironaphthopyrans (96-99) and
indolinospironaphtho-1,4- oxazine (100) were synthesized by an aldol type of condensation of equimolar amounts of
1’,3’,3’-trimethyl-20-methyleneindoline and its 5’-substituted derivatives with 2-hydroxybenzaldehyde substituted with a nitro or methoxy group at position 6 or 7,1-hydroxy-2-naphthaldehyde, 2-hydroxy-1 naphth- aldehyde or 1-nitroso- 2-naphthol. This reaction
involves nucleophilic attack of the enamine to
the carbonyl or nitroso group and subsequent ring
closure by intramolecular addition of the phenolic
oxygen to the immonium group which gave under
elimination of water the spiro-compounds (93-95, 96-99 and 100). Proof of the stereostructures of 100 was obtained by the single-crystal
X-ray diffraction method. A substituted indoline ring and the benzopyran ring
in 101 and the naphtho-1, 4-oxazine
moiety in 100 are interconnected via
the common chiral atom and positioned almost perpendicularly to each other. The
five-membered 2, 3-dihydropyrrolo moiety of the indoline ring adopts an
envelope conformation in both structures (Scheme 18).
________________
50. S. Raić-Malić, L. Tomašković, D. Mrvoš-Sermek, B. Prugovećki, M. Cetina, M. Grdiša, K. Paveliš, A. Mannschreck,
J. Balzarini, E. D. Clercqf, and M. Mintasa, Bioorg.Med. Chem., 2004, 12, 1037.
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