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2004
Oxazine derivatives
R 0595
Transformation Reactions of the Betti Base Analogue Aminonaphthols. —
tri-, tetra- or pentacyclic oxazines are synthesized by means of
44- 184 Naphthalene-condensed
simple or domino ring-closure reactions of Betti base (Ib) and its analogues (Ia) and
(XIV) with aldehydes (II), (IX) and (XII), phosgene (IV), phenyl isothiocyanate (VI),
formalin, ethyl benzimidate and levulinic acid. The polycyclic derivatives of (Ib) and
(XIV) containing asymmetric centers are formed with nearly complete diastereoselectivity. Due to the different stabilities of (I) and (XIV), considerable differences in the
cyclization behavior of the unsubstituted and substituted aminonaphthols (Ia) and (Ib)
and of the regioisomeric compounds (Ib) and (XIV) are observed. — (SZATMARI, I.;
HETENYI, A.; LAZAR, L.; FUELOEP*, F.; J. Heterocycl. Chem. 41 (2004) 3,
367-373; Inst. Pharm. Chem., Univ. Szeged, H-6701 Szeged, Hung.; Eng.) —
H. Hoennerscheid
2004
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