Cleavage of the C-C triple bond of ketoalkynes: synthesis of 4(3H)-quinazolinones

被引：105
作者：
Yang, Xifa [1 ,2 ,3 ]
Cheng, Guolin [1 ,2 ,3 ]
Shen, Jinhai [1 ,2 ,3 ]
Kuai, Changsheng [1 ,2 ,3 ]
Cui, Xiuling [1 ,2 ,3 ]
机构：
[1] Huaqiao Univ, Inst Mol Med, Key Lab Xiamen Marine & Gene Drugs, Xiamen 361021, Peoples R China
[2] Huaqiao Univ, Sch Biomed Sci, Xiamen 361021, Peoples R China
[3] Minist Educ, Engn Res Ctr Mol Med, Xiamen 361021, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2015年 / 2卷 / 04期
关键词：
METAL-FREE CONDITIONS; REGIOSPECIFIC SYNTHESIS; QUINAZOLINONES; CASCADE; INHIBITORS; AMIDATION; ALCOHOLS; POTENT;
D O I：
10.1039/c4qo00260a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel protocol for the synthesis of 4(3H)-quinazolinones via selective cleavage of the triple bond of ketoalkynes under oxidant-, metal-, and ligand-free conditions has been developed. Various 4(3H)-quinazolinones were obtained through fragmentation of the C-C triple bond and formation of two C-N bonds.
引用
收藏
页码：366 / 368
页数：3
相关论文
共 33 条
[1]   Synthesis of some new 4(3H)-quinazolinone-2-carboxaldehyde thiosemicarbazones and their metal complexes and a study on their anticonvulsant, analgesic, cytotoxic and antimicrobial activities - Part-1 [J].
Aly, Mohsen M. ;
Mohamed, Yahia A. ;
El-Bayouki, Khairy A. M. ;
Basyouni, Wahid M. ;
Abbas, Samir Y. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (08) :3365-3373
[2]   Microwave activated synthesis of 2-aryl-qlainazolin-4(3H) ones [J].
Bakavoli, M. ;
Sabzevari, O. ;
Rahimizadeh, M. .
CHINESE CHEMICAL LETTERS, 2007, 18 (12) :1466-1468
[3]  
CHEN A. LING, 1933, JOUR AMER PHARM ASSOC, V22, P716
[4]   A Metal-Free Multicomponent Cascade Reaction for the Regiospecific Synthesis of 1,5-Disubstituted 1,2,3-Triazoles [J].
Cheng, Guolin ;
Zeng, Xiaobao ;
Shen, Jinhai ;
Wang, Xuesong ;
Cui, Xiuling .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (50) :13265-13268
[5]   ANTIMALARIAL CONSTITUENTS OF CHINESE DRUG, CHANG SHAN, DICHROA-FEBRIFUGA LOUR [J].
CHOU, TQ ;
FU, FY ;
KAO, YS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (05) :1765-1767
[6]   Highly efficient solvent-free synthesis of quinazolin-4(3H)-ones and 2,3-dihydroquinazolin-4(1H)-ones using tetrabutylammonium bromide as novel ionic liquid catalyst [J].
Davoodnia, A. ;
Allameh, S. ;
Fakhari, A. R. ;
Tavakoli-Hoseini, N. .
CHINESE CHEMICAL LETTERS, 2010, 21 (05) :550-553
[7]   A POTENT, ORALLY-ACTIVE, BALANCED AFFINITY ANGIOTENSIN-II AT(1) ANTAGONIST AND AT(2) BINDING INHIBITOR [J].
DELASZLO, SE ;
QUAGLIATO, CS ;
GREENLEE, WJ ;
PATCHETT, AA ;
CHANG, RSL ;
LOTTI, VJ ;
CHEN, TB ;
SCHECK, SA ;
FAUST, KA ;
KIVLIGHN, SS ;
SCHORN, TS ;
ZINGARO, GJ ;
SIEGL, PKS .
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (21) :3207-3210
[8]  
Habib O M, 1995, Boll Chim Farm, V134, P503
[9]   Pd-Catalyzed Benzylic C-H Amidation with Benzyl Alcohols in Water: A Strategy To Construct Quinazolinones [J].
Hikawa, Hidemasa ;
Ino, Yukari ;
Suzuki, Hideharu ;
Yokoyama, Yuusaku .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (16) :7046-7051
[10]   Synthesis and biological evaluation of some new fused quinazoline derivatives [J].
Ibrahim, SS ;
AbdelHalim, AM ;
Gabr, Y ;
ElEdfawy, S ;
AbdelRahman, RM .
JOURNAL OF CHEMICAL RESEARCH-S, 1997, (05) :154-155
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