Synthesis of novel 5-monoalkylbarbiturate derivatives: new access to 1,2-oxazepines

被引：16

作者：

Barakat, Assem ^{[1
,3
]}

Islam, Mohammad Shahidul ^{[1
]}

Al-Majid, Abdullah M. ^{[1
]}

Soliman, Saied M. ^{[2
,3
]}

Mabkhot, Yahia N. ^{[1
]}

Al-Othman, Zeid Abdullah ^{[1
]}

Ghabbour, Hazem A. ^{[4
]}

Fun, Hoong-Kun ^{[4
,5
]}

机构：

[1] King Saud Univ, Dept Chem, Coll Sci, Riyadh 11451, Saudi Arabia

[2] Rabigh Coll Sci & Art, Dept Chem, Rabigh 21911, Saudi Arabia

[3] Univ Alexandria, Fac Sci, Dept Chem, Alexandria 21321, Egypt

[4] King Saud Univ, Coll Pharm, Dept Pharmaceut Chem, Riyadh 11451, Saudi Arabia

[5] Univ Sains Malaysia, Sch Phys, Xray Crystallog Unit, George Town 11800, Malaysia

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 50期

关键词：

Michael addition; Barbituric acid; Nitrogen heterocycles; Oxazepines; DFT; BARBITURIC-ACID DERIVATIVES; FRIEDEL-CRAFTS ALKYLATION; POT SEQUENTIAL SYNTHESIS; MOLECULAR-STRUCTURE; SPIRO;

D O I：

10.1016/j.tetlet.2015.10.108

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and straightforward route to 5-monoalkylbarbiturates by the NHEt2 catalyzed Michael reaction of 1,3-dimethylbarbituric acid and alpha,beta-unsaturated ketones is described. Significantly, the reaction exclusively furnished 5-monoalkylbarbiturates. Under neat conditions, the mixing and grinding of a representative 1,5-diketone and hydroxylamine hydrochloride gave the corresponding 1,2-oxazepine in very good yield. (C) 2015 Elsevier Ltd. All rights reserved.

引用

收藏

页码：6984 / 6987

页数：4

相关论文

共 44 条

[1]

Ahmed A. H., 2010, SYNTHESIS-STUTTGART, V2, P304

[2] Facile and Promising Method for Michael Addition of Indole and Pyrrole to Electron-Deficient trans-β-Nitroolefins Catalyzed by a Hydrogen Bond Donor Catalyst Feist's Acid and Preliminary Study of Antimicrobial Activity [J].

Al Majid, Abdullah M. A. ;

Islam, Mohammad Shahidul ;

Barakat, Assem ;

Al-Agamy, Mohamed H. M. ;

Naushad, Mu .

SCIENTIFIC WORLD JOURNAL, 2014,

[3] Synthesis, in vitro biological activities and in silico study of dihydropyrimidines derivatives [J].

Barakat, Assem ;

Islam, Mohammad Shahidul ;

Al-Majid, Abdullah Mohammed ;

Ghabbour, Hazem A. ;

Fun, Hoong-Kun ;

Javed, Kulsoom ;

Imad, Rehan ;

Yousuf, Sammer ;

Choudhary, M. Iqbal ;

Wadood, Abdul .

BIOORGANIC & MEDICINAL CHEMISTRY, 2015, 23 (20) :6740-6748

[4] Synthesis and structure investigation of novel pyrimidine-2,4,6-trione derivatives of highly potential biological activity as anti-diabetic agent [J].

Barakat, Assem ;

Soliman, Saied M. ;

Al-Majid, Abdullah Mohammed ;

Lotfy, Gehad ;

Ghabbour, Hazem A. ;

Fun, Hoong-Kun ;

Yousuf, Sammer ;

Choudhary, M. Iqbal ;

Wadood, Abdul .

JOURNAL OF MOLECULAR STRUCTURE, 2015, 1098 :365-376

[5] Synthesis, molecular structure investigations and antimicrobial activity of 2-thioxothiazolidin-4-one derivatives [J].

Barakat, Assem ;

Al-Najjar, Hany J. ;

Al-Majid, Abdullah Mohammed ;

Soliman, Saied M. ;

Mabkhot, Yahia Nasser ;

Al-Agamy, Mohamed H. M. ;

Ghabbour, Hazem A. ;

Fun, Hoong-Kun .

JOURNAL OF MOLECULAR STRUCTURE, 2015, 1081 :519-529

[6] Zwitterionic pyrimidinium adducts as antioxidants with therapeutic potential as nitric oxide scavenger [J].

Barakat, Assem ;

Al-Majid, Abdullah Mohammed ;

Al-Najjar, Hany J. ;

Mabkhot, Yahia Nasser ;

Javaid, Sumaira ;

Yousuf, Sammer ;

Choudhary, M. Iqbal .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 84 :146-154

[7] An efficient and green procedure for synthesis of rhodanine derivatives by aldol-thia-Michael protocol using aqueous diethylamine medium [J].

Barakat, Assem ;

Al-Majid, Abdullah M. ;

Al-Najjar, Hany J. ;

Mabkhot, Yahia N. ;

Ghabbour, Hazem A. ;

Fun, Hoong-Kun .

RSC ADVANCES, 2014, 4 (10) :4909-4916

[8] Highly enantioselective Friedel-Crafts alkylation of indoles with α,β-unsaturated ketones with simple Cu(II)-oxazoline-imidazoline catalysts [J].

Barakat, Assem ;

Islam, Mohammad Shahidul ;

Al Majid, Abdullah M. A. ;

Al-Othman, Zeid Abdullah .

TETRAHEDRON, 2013, 69 (25) :5185-5192

[9]

Bremner J. B., 1996, COMPREHENSIVE HETERO, V9, P183

[10] PYRIDO[2,3-D]PYRIMIDINES .4. SYNTHETIC STUDIES LEADING TO VARIOUS OXOPYRIDO[2,3-D]PYRIMIDINES [J].

BROOM, AD ;

SHIM, JL ;

ANDERSON, GL .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (07) :1095-1099

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