Synthesis of 2H-1,4-Benzoxazin-3(4H)-ones via Smiles Rearrangement

被引：0

作者：

Zhou, Jia-Zhou ^{[1
]}

Li, Zhu-Bo ^{[1
]}

Yang, Hao ^{[2
]}

He, Xiao-Yan ^{[1
]}

Wang, Li-Ying ^{[1
]}

Tian, Xiao ^{[1
]}

Lv, Ting Ting ^{[1
]}

Zuo, Hua ^{[1
]}

机构：

[1] Southwest Univ, Coll Pharmaceut Sci, Chongqing 400715, Peoples R China

[2] Southwest Univ, Coll Hort & Landscape Architecture, Chongqing 400715, Peoples R China

来源：

ASIAN JOURNAL OF CHEMISTRY | 2011年 / 23卷 / 07期

基金：

中国国家自然科学基金;

关键词：

Smiles rearrangement; 2H-1,4-Benzoxazin-3(4H)-one; Synthesis; Hindered molecule; DERIVATIVES; DESIGN; INHIBITORS;

D O I：

暂无

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient synthetic route for novel 2H-1,4-benzoxazin-3(4H)-ones via smiles rearrangement is developed. Reaction of primary amine and chloroacetyl chloride gave 2-chloroacetamide, which reacted with 2-chlorophenol, followed by Smiles rearrangement to obtain a series of new 2H-1,4-benzoxazin-3(4H)-ones (yield 45-90 %).

引用

页码：2947 / 2950

页数：4

共 16 条

[1] AN INVESTIGATION OF THE ELECTRONIC SPECTRAL PROPERTIES OF THE MEROCYANINES DERIVED FROM PHOTOCHROMIC SPIROINDOLINONAPHTH[2,1-B][1,4]OXAZINES [J].

CHRISTIE, RM ;

AGYAKO, CK ;

MITCHELL, K .

DYES AND PIGMENTS, 1995, 29 (03) :241-250

[2] Anti-Candida albicans properties of novel benzoxazine analogues [J].

Fringuelli, R ;

Pietrella, D ;

Schiaffella, F ;

Guarraci, A ;

Perito, S ;

Bistoni, F ;

Vecchiarelli, A .

BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (06) :1681-1686

[3] Synthesis of novel 1,4-benzoxazin-3-one derivatives as inhibitors against tyrosine kinases [J].

Honda, Takahiro ;

Terao, Takahiro ;

Aono, Hiroyuki ;

Ban, Masakazu .

BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (02) :699-708

[4]

Hua Z, 2008, B KOREAN CHEM SOC, V29, P1379

[5] Design and synthesis of phenethyl benzo[1,4]oxazine-3-ones as potent inhibitors of PI3Kinaseγ [J].

Lanni, Thomas B., Jr. ;

Greene, Keri L. ;

Kolz, Christine N. ;

Para, Kimberly S. ;

Visnick, Melean ;

Mobley, James L. ;

Dudley, David T. ;

Baginski, Theodore J. ;

Liimatta, Marya B. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (03) :756-760

[6] ELECTROCHEMICALLY ACTIVE NANOCRYSTALLINE SNO2 SURFACE MODIFICATION WITH THIAZINE AND OXAZINE DYE AGGREGATES [J].

LIU, D ;

KAMAT, PV .

JOURNAL OF THE ELECTROCHEMICAL SOCIETY, 1995, 142 (03) :835-839

[7] Synthesis of 2-(4-substitutedmethylpiperazin-1-yl)-N-(3,4-dihydro-3-oxo-2H-benzo[b][1,4]oxazin-7-yl)acetamides and their positive inotropic evaluation [J].

Liu, Xue-Kun ;

Cui, Xun ;

Hong, Lan ;

Sun, Liang-Peng ;

Quan, Zhe-Shan ;

Piao, Hu-Ri .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (07) :3027-3031

[8] 1,4-benzothiazine and 1,4-benzoxazine imidazole derivatives with antifungal activity: A docking study [J].

Macchiarulo, A ;

Costantino, G ;

Fringuelli, D ;

Vecchiarelli, A ;

Schiaffella, F ;

Fringuelli, R .

BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (11) :3415-3423

[9] Synthesis of novel 7-benzylamino-2H-1,4-benzoxazin-3(4H)-ones as anticonvulsant agents [J].

Piao, Zhong-Tai ;

Guan, Li-Ping ;

Zhao, Li-Ming ;

Piao, Hu-Ri ;

Quan, Zhe-Shan .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (06) :1216-1221

[10] Rational design of 6-(2,4-diaminopyrimidinyl)-1,4-benzoxazin-3-ones as small molecule renin inhibitors [J].

Powell, Noel A. ;

Ciske, Fred L. ;

Cai, Cuiman ;

Holsworth, Daniel D. ;

Mennen, Ken ;

Van Huis, Chad A. ;

Jalaie, Mehran ;

Day, Jacqueline ;

Mastronardi, Michelle ;

McConnell, Pat ;

Mochalkin, Igor ;

Zhang, Erli ;

Ryan, Michael J. ;

Bryant, John ;

Collard, Wendy ;

Ferreira, Suzie ;

Gu, Chungang ;

Collins, Roxane ;

Edmunds, Jeremy J. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (17) :5912-5949

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