Synthesis of Flavones and ?-Benzopyranones Using Mild Sonogashira Coupling and 18-Crown-6 Ether Mediated 6-endo Cyclization

被引:23
作者
Chuang, Da-Wei [1 ]
El-Shazly, Mohamed [1 ,2 ]
Balaji, Barve D. [1 ,3 ]
Chung, Yu-Ming [1 ]
Chang, Fang-Rong [1 ]
Wu, Yang-Chang [1 ,4 ,5 ,6 ]
机构
[1] Kaohsiung Med Univ, Grad Inst Nat Prod, Kaohsiung 807, Taiwan
[2] Ain Shams Univ, Fac Pharm, Dept Pharmacognosy & Nat Prod Chem, Cairo 11566, Egypt
[3] Kaohsiung Med Univ, Dept Med & Appl Chem, Kaohsiung 807, Taiwan
[4] China Med Univ, Coll Chinese Med, Sch Chinese Med, Taichung 404, Taiwan
[5] China Med Univ Hosp, Nat Med Prod Res Ctr, Taichung 404, Taiwan
[6] China Med Univ Hosp, Ctr Mol Med, Taichung 404, Taiwan
关键词
Synthetic methods; Oxygen heterocycles; Cross-coupling; Cyclization; Michael addition; BIOLOGICAL EVALUATION; EFFICIENT SYNTHESIS; PHASE-II; FLAVOPIRIDOL; CHROMONES; ANALOGS; KETONES; 4H-CHROMEN-4-ONES; COMBINATION; FLAVOXATE;
D O I
10.1002/ejoc.201200529
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient method for the synthesis of flavones and ?-benzopyranones has been developed utilizing a mild Sonogashira coupling and 18-crown-6 ether mediated 6-endo cyclization of o-alkynoylphenyl acetates. By using this strategy, flavones and ?-benzopyranones bearing electron-donating groups, halogens, and simple alkyl substituents were synthesized in satisfactory yields.
引用
收藏
页码:4533 / 4540
页数:8
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