Saturated heterocycles. 254Part 253: R. Sillanpää, E. Forró, F. Fülöp, G. Bernáth, Acta Chem. Scand., submitted for publication; Part 252: F. Fülöp, J. Tari, G. Bernáth, P. Sohár, A. Dancsó, Gy. Argay and A. Kálmán, Liebigs Ann. Chem., 34, 289 1997; Part 251: F. Fülöp, E. Forró, G. Bernáth, I. Miskolczi, A. Martinsen and P. Vainiotalo: J. Heterocyclic Chem., 34, 1167 1997.. synthesis and stereochemistry of saturated or partially saturated pyridazino6,1b and phthalazino1,2bquinazolinones

Autor: Bernáth, GÁBor, Miklós, Ferenc, Stájer, GÉZa, Sohár, PÁL, Böcskei, Zsolt, Menyhárd, DÓRa
Zdroj: Journal of Heterocyclic Chemistry; January 1998, Vol. 35 Issue: 1 p201-208, 8p
Abstrakt: By the reaction of anthranilic hydrazide 1with cis2pmethylbenzoyl1cyclohexanecarboxylic acid 2aor diendo3pmethylbenzoylbicyclo2.2.1heptane2carboxylic acid 2b, fused tetra and pentacyclic ring systems 3a, bwere prepared, trans2Amino1cyclohexanecarbohydrazide 4bwas reacted with 3pchlorobenzoylpropionic acid 5to yield the pyridazino6,1bquinazolinone 6. From the reaction of cis2amino1cyclohexanecarbohydrazide 4awith 2a, three isomeric partially saturated 8Hphthalazino1,2bquinazolin8ones 7acwere formed. The reaction of diexo2aminobicyclo2.2.1heptane3carbohydrazide 4cand 2afurnished the pentacyclic derivatives 8and 9containing a 3aryl4,5dihydropyridazine or 3arylhexahydropyridazine ring Cwith cisannelated CDrings. The formation of 8and 9involving different ring systems can be rationalized by two reaction pathways: i in the bislactam 9the carboxyl group acylates the hydrazide, while ii in 8it forms a pyridazine ring with the cyclic amino group by cyclocondensation. The structures of the products were elucidated by 1H and 13C nmr methods, including DEPT, DNOE and 2DHSC measurements.
Databáze: Supplemental Index
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