STEREOCHEMICAL STUDIES .167. SATURATED HETEROCYCLES .208. PREPARATIONAND STERIC STRUCTURE OF 3(2H)PYRIDAZINONES AND 1,2-OXAZIN-6-ONES FUSED WITH 3-MEMBERED TO 6-MEMBERED SATURATED CARBOCYCLES OR NORBORNANE SKELETON

Reactions of cis-2-(4-methylbenzoyl)-cyclopropane- (1) and -cyclobutan ecarboxylic acids (2), the stereoisomeric cyclohexyl homologues (3 and 4), and di-endo-3-(4-methylbenzoyl)-bi-cyclo [2.2.1]heptane-2-carboxy lic acid (5) with hydrazines yield the cycloalkane-condensed (3(2H)pyr idazinones 6-9 and the norbornane di-endo-fused derivatives 10. With h ydroxylamine, compounds 1 and 3-5 were transformed to the cycloalkane- and norbornane-condensed 1,2-oxazin-6-ones 11-14. Transformation of 3 -5 led to the trans-hexahydroanthrone 17a and its methylene-bridged an alogue 24. From the stereoisomeric hexahydro-1(3H)-isobenzofuranones 2 0 and 21, the partly saturated anthrones were also prepared; the produ cts (16b and 17b) contain the methyl substituent in position 6. On red uction, 16b yield the 2-methyloctahydroanthracene 22. The structures o f tl;e compounds were proved by H-1 and C-13 NMR spectroscopy, making use of NOE, DEFT, and CH-COSY techniques.