Synthesis of Novel Xanthene-dione Derivatives Containing 2-Quinolone Moiety
WANG Xuan1, ZHANG Zhen-ming1,2, WANG Run-nan2, ZHANG Dan-dan2, LI Shu-an2
1. School of Chemical Technology, China University of Mining and Technology, Xuzhou 221116, China; 2. School of Chemical Technology, Huaihai Institute of Technology, Lianyungang 222005, China
Abstract:Five novel xanthene-dione derivatives containing 2-quinolone moiety were synthesized in yields of 78%~90% by reaction of substituted 2-chloroquinoline-3-carbaldehyde with 5,5-dimethyl-1,3-cyclohexanedione, using acetic acid as catalyst and DMF as solvent at 80 ℃~100 ℃ for 2.5 h~4.0 h.The structures were characterized by 1H NMR, IR, HR-ESI-MS and elemental analysis. X-ray single crystal diffractometer of 3,3,6,6-tetramethyl-9-{3-[7-methylquinolyl-2(1H)-one]}-2,4,5,7,9,10-hexahydro-xantene-1,8(2H,5H)-dione(3b) tests indicated that 3b(CCDC: 971 833) belongs to monoclinic crystal system, space group C12/C1 with a=1.411 90(16)nm, b=2.231 4(2)nm, c=1.618 28(18)nm, β=106.904°, V=4.878 1(9) nm3, Dc=1.175 g·cm-3, Z=1, R1=0.044 4, wR2=0.074 6.