Cyclopentanone The Diene Sodium Acylation Reaction

Generally, fulvenes are typical nonaromatic compounds which are prone to dimerize due to thermodynamic instability. We have synthesized a series of stable 1,6-disubsu'tuted fulvenes ( I ) having seven-membered ring containing chelated hydrogen from the reaction of cyclopentadienyl sodium with acyl chloride. Meanwhile, the related fulvene esters ( II ) are also derived from the reaction. Thereafter, we synthesized compounds (III) having novel conjugated system by the same process. In addition, compounds ( I ) with different 1,6-disubstitutions were also obtained from the reaction between a different acyl chloride and acyl cyclopentadienyl sodium.When we ran reaction of cyclopentadienyl sodium with different diacyl chlorides ClCO(CH2)nCOCl, We found some novel fulvenes (1) difulvenyl furan (IV) (n=2); (2) fulvenyl lactone (V) (n=3, 4); (3) futvenyl macrolide (VI) (n=6, 8).In this dissertation, we have prepared 2H-cyclopentapyridazine ( VII) successfully using compound ( I ) as the reactant. On the other hand, a new kind of cyclopentanes (VIII) with diacyl substituents are obtained by catalytic hydrogenation of compounds ( I ). Finally, we explored the synthetic approach to hydrazulene and got a compound (IX).This dissertation have synthesized about 40 unreported compounds with seven main types of structures as well as some known compounds such as acyl chlorides.The results of preliminary pharmacological tests on some compounds (I) and (IV) have shown that: 1) (TV) have some anticancer effects on HL-60 and HCT-8. 2) ( I ) R₁=R₂=C₃H₇ shows anticancer and antilipid peroxidative effect. 3) (III) and (IV) can inhibit the growth of leucocytic sarcoma and oral carcinoma, respectively. 4) compound( II) R₁=R₂=3, 4, 5,-trimethoxyphenyl can inhibit the growth KB cell.