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200517.fm Page 185 Friday, March 18, 2005 2:52 PM
2005
Oxazine derivatives
R 0595
Synthesis and Stereostructure of Saturated Isoindolone-Fused Hetero Tri-, Tetra-,
Pentacyclic Compounds. — Cyclohexanecarboxylic acid (I) is subjected to reac17- 166 and
tions with ethylenediamine (II) and cyclic amino alcohols (V), (VII), (IX), (XI), and
(XIII) to prepare fused isoindolones. The reaction of (I) with (II) yields diastereomeric
trans-imidazoisoindoles (III) and (IV) while cyclization of (I) with cis-aminocyclohexane- or cyclohexenemethanol results in trans-isoindolobenzoxazines, e.g. (VI). Endoand exo-norbornane- and-norborneneamine alcohols (VII), (IX), and (XI) upon reaction with (I) afford the corresponding methylene-bridged derivatives. In the case of
endo-norbornane amino alcohol (XIII), a mixture of diastereomers is obtained. The cis,
endo or exo nature of the amino alcohols applied is exclusively retained in the cyclic
products. — (SOHAR*, P.; CSAMPAI, A.; MAGYARFALVI, G.; SZABO, A. E.;
STAJER, G.; Monatsh. Chem. 135 (2004) 12, 1519-1527; Dep. Gen. Inorg. Chem.,
Eoetvoes Lorand Univ., H-1518 Budapest, Hung.; Eng.) — H. Hoennerscheid
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