Regioselective construction of diverse and multifunctionalized 2-hydroxybenzophenones for sun protection by indium(III)-catalyzed benzannulation

被引：36

作者：

Cai, Hongyun ^{[1
]}

Xia, Likai ^{[1
]}

Lee, Yong Rok ^{[1
]}

机构：

[1] Yeungnam Univ, Sch Chem Engn, Gyongsan 712749, South Korea

来源：

CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 49期

基金：

新加坡国家研究基金会;

关键词：

IN-VITRO; BENZOPHENONE; DERIVATIVES; OXYBENZONE; ALDEHYDES; ANALOGS; ALKYNES; DESIGN; AGENTS; ARENES;

D O I：

10.1039/c6cc02381a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Diverse and functionalized 2-hydroxybenzophenone derivatives were synthesized efficiently in good to excellent yield via the highly regioselective indium(III)-catalyzed [2+2+2] benzannulation of 3-formylchromones with beta-enamino esters or beta-enamino ketones. This benzannulation reaction proceeds via a domino Michael/retro-Michael/6 pi-electrocyclization/deformylation reaction. In addition, 2-hydroxybenzophenones were also prepared by the indium(III)-catalyzed [4+2] benzannulation reaction between 3-substituted chromen-4-ones and beta-enamino esters or beta-enamino ketones. Furthermore, the effects of substituents and pi conjugation on the characteristics of the UV-Vis spectrum of synthesized 2-hydroxybenzophenones were examined. Compound 10s exhibited higher sun protection activity than oxybenzone which is used in most popular sunscreens.

引用

页码：7661 / 7664

页数：4

共 39 条

[1] Probing the Ultrafast Energy Dissipation Mechanism of the Sunscreen Oxybenzone after UVA Irradiation [J].

Baker, Lewis A. ;

Horbury, Michael D. ;

Greenough, Simon E. ;

Coulter, Philip M. ;

Karsili, Tolga N. V. ;

Roberts, Gareth M. ;

Orr-Ewing, Andrew J. ;

Ashfold, Michael N. R. ;

Stavros, Vasilios G. .

JOURNAL OF PHYSICAL CHEMISTRY LETTERS, 2015, 6 (08) :1363-1368

[2] Higher triplet excited states of benzophenones and bimolecular triplet energy transfer measured by using nanosecond-picosecond two-color/two-laser flash photolysis [J].

Cai, XC ;

Sakamoto, M ;

Fujitsuka, M ;

Majima, T .

CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (22) :6471-6477

[3]

Cotton F.A., 1999, Advanced Inorganic Chemistry

[4] Structure-Guided Design of Thiazolidine Derivatives as Mycobacterium tuberculosis Pantothenate Synthetase Inhibitors [J].

Devi, Parthiban Brindha ;

Samala, Ganesh ;

Sridevi, Jonnalagadda Padma ;

Saxena, Shalini ;

Alvala, Mallika ;

Salina, Elena G. ;

Sriram, Dharmarajan ;

Yogeeswari, Perumal .

CHEMMEDCHEM, 2014, 9 (11) :2538-2547

[5] PHARMACOKINETIC-PHARMACODYNAMIC INTERACTION BETWEEN THE COMT INHIBITOR TOLCAPONE AND SINGLE-DOSE LEVODOPA [J].

DINGEMANSE, J ;

JORGA, K ;

ZURCHER, G ;

SCHMITT, M ;

SEDEK, G ;

DAPRADA, M ;

VANBRUMMELEN, P .

BRITISH JOURNAL OF CLINICAL PHARMACOLOGY, 1995, 40 (03) :253-262

[6] A Sulfur Ylides-Mediated Domino Benzannulation Strategy to Construct Biaryls, Alkenylated and Alkynylated Benzene Derivatives [J].

Gao, Fei ;

Huang, You .

ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (11-12) :2422-2428

[7] Synthesis and evaluation of in vitro antimicrobial activity of novel 2-[2-(aroyl)aroyloxy]methyl-1,3,4-oxadiazoles [J].

Girish, V. ;

Khanum, Noor Fatima ;

Gurupadaswamy, H. D. ;

Khanum, Shaukath Ara .

RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2014, 40 (03) :330-335

[8]

Goossen LJ, 2001, ANGEW CHEM INT EDIT, V40, P3458, DOI 10.1002/1521-3773(20010917)40:18<3458::AID-ANIE3458>3.0.CO

[9]

2-0

[10] Regioselective Synthesis of Substituted Arenes via Aerobic Oxidative [3+3] Benzannulation Reactions of α,β-Unsaturated Aldehydes and Ketones [J].

Joshi, Prabhakar Ramchandra ;

Undeela, Sridhar ;

Reddy, Doni Dhanoj ;

Singarapu, Kiran Kumar ;

Menon, Rajeev S. .

ORGANIC LETTERS, 2015, 17 (06) :1449-1452

← 1 2 3 4 →