Efficient synthesis of substituted 2-(4H-1,3-benzoxazin-2-yl) phenols via a pseudo three-component reaction

被引:1
作者
Wang, Ting [1 ]
Dai, Chenlu [1 ]
Qing, Xushun [1 ]
Wang, Cunde [1 ]
机构
[1] Yangzhou Univ, Sch Chem & Chem Engn, 180 Siwangting St, Yangzhou 225002, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
4H-1,3-benzoxazine; pseudo three-component reaction; substituted; 2-hydroxybenzaldehyde; oxazine; annulation reaction; DNA-PK; INHIBITORS; PI3K; ALDEHYDES; DESIGN; POTENT;
D O I
10.3184/174751918X15199181776822
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient pseudo three-component reaction between substituted 2-hydroxybenzaldehydes and ammonium acetate for the preparation of substituted 2-(4H-1,3-benzoxazin-2-yl) phenols in moderate to good yields (70-80%) was developed. The structure of a typical product was confirmed by X-ray crystallography.
引用
收藏
页码:121 / 124
页数:4
相关论文
共 23 条
[1]   Synthesis, antimicrobial activity and QSARs of new benzoxazine-3-ones [J].
Alper-Hayta, S. ;
Aki-Sener, E. ;
Tekiner-Gulbas, B. ;
Yildiz, I. ;
Temiz-Arpaci, O. ;
Yalcin, I. ;
Altanlar, N. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2006, 41 (12) :1398-1404
[2]   The leupyrrins:: A structurally unique family of secondary metabolites from the myxobacterium Sorangium cellulosum [J].
Bode, HB ;
Irschik, H ;
Wenzel, SC ;
Reichenbach, H ;
Müller, R ;
Höfle, G .
JOURNAL OF NATURAL PRODUCTS, 2003, 66 (09) :1203-1206
[3]   Modified Salicylanilide and 3-Phenyl-2H-benzo[e][1,3]oxazine-2,4(3H)-dione Derivatives as Novel Inhibitors of Osteoclast Differentiation and Bone Resorption [J].
Chen, Chun-Liang ;
Liu, Fei-Lan ;
Lee, Chia-Chung ;
Chen, Tsung-Chih ;
Ali, Ahmed Atef Ahmed ;
Sytwu, Huey-Kang ;
Chang, Deh-Ming ;
Huang, Hsu-Shan .
JOURNAL OF MEDICINAL CHEMISTRY, 2014, 57 (19) :8072-8085
[4]   Oxoazabenzo[de]anthracenes conjugated to amino acids:: Synthesis and evaluation as DNA-binding antitumor agents [J].
Dias, N ;
Goossens, JF ;
Baldeyrou, B ;
Lansiaux, A ;
Colson, P ;
Di Salvo, A ;
Bernal, J ;
Turnbull, A ;
Mincher, DJ ;
Bailly, C .
BIOCONJUGATE CHEMISTRY, 2005, 16 (04) :949-958
[5]   2-(4H-1,3-Benzoxazin-2-yl)phenol [J].
Fernandes, Christiane ;
Horn, Adolfo, Jr. ;
Howie, R. Alan ;
Schripsma, Jan ;
Wardell, James L. ;
Tiekink, Edward R. T. .
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 :O3104-U706
[6]   Aza-Wittig reaction, carbodiimide-mediated ring closure, and enol-induced ring interconversion:: A domino process for the synthesis of 4-methylene-4H-3,1-benzoxazines [J].
Fresneda, Pilar M. ;
Bleda, Juan Antonio ;
Angel, Miguel Sanz ;
Molina, Pedro .
SYNLETT, 2007, (10) :1541-1544
[7]   2-amino-4H-3,1-benzoxazin-4-ones as inhibitors of C1r serine protease [J].
Hays, SJ ;
Caprathe, BW ;
Gilmore, JL ;
Amin, N ;
Emmerling, MR ;
Michael, W ;
Nadimpalli, R ;
Nath, R ;
Raser, KJ ;
Stafford, D ;
Watson, D ;
Wang, K ;
Jaen, JC .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (07) :1060-1067
[8]   Synthesis, DNA-PK inhibition, anti-platelet activity studies of 2-(N-substituted-3-aminopyridine)-substituted-1,3-benzoxazines and DNA-PK and PI3K inhibition, homology modelling studies of 2-morpholino-(7,8-di and 8-substituted)-1,3-benzoxazines [J].
Ihmaid, Saleh K. ;
Al-Rawi, Jasim M. A. ;
Bradley, Christopher J. ;
Angove, Michael J. ;
Robertson, Murray N. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 57 :85-101
[9]   Potent, novel in vitro inhibitors of the Pseudomonas aeruginosa deacetylase LpxC [J].
Kline, T ;
Andersen, NH ;
Harwood, EA ;
Bowman, J ;
Malanda, A ;
Endsley, S ;
Erwin, AL ;
Doyle, M ;
Fong, S ;
Harris, AL ;
Mendelsohn, B ;
Mdluli, K ;
Raetz, CRH ;
Stover, CK ;
Witte, PR ;
Yabannavar, A ;
Zhu, SG .
JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (14) :3112-3129
[10]   DESIGN AND SYNTHESIS OF 4H-3,1-BENZOXAZIN-4-ONES AS POTENT ALTERNATE SUBSTRATE-INHIBITORS OF HUMAN-LEUKOCYTE ELASTASE [J].
KRANTZ, A ;
SPENCER, RW ;
TAM, TF ;
LIAK, TJ ;
COPP, LJ ;
THOMAS, EM ;
RAFFERTY, SP .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (02) :464-479