One-Pot Multicomponent Coupling Reaction of Catechols, Benzyl Alcohols/Benzyl Methyl Ethers, and Ammonium Acetate toward Synthesis of Benzoxazoles

被引：17

作者：

Aboonajmi, Jasem ^{[1
]}

Panahi, Farhad ^{[1
]}

Sharghi, Hashem ^{[1
]}

机构：

[1] Shiraz Univ, Coll Sci, Dept Chem, Shiraz 71454, Iran

来源：

ACS OMEGA | 2021年 / 6卷 / 34期

关键词：

AEROBIC OXIDATION; AMINES; EFFICIENT; SYSTEM; RING;

D O I：

10.1021/acsomega.1c03207

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The multicomponent coupling reaction of catechol, ammonium acetate, and benzyl alcohol/benzyl methyl ether in the presence of a Fe(III) catalyst precursor afforded benzoxazole derivatives in good to excellent yields. The notable features of this protocol are abundant availability of the catalyst system, large-scale synthesis, high diversity, and high yields of products.

引用

页码：22395 / 22399

页数：5

共 31 条

[1] Consecutive Oxidation/Condensation/Cyclization/Aromatization Sequences Catalyzed by Nanostructured Iron(III)-Porphyrin Complex towards Benzoxazole Derivatives [J].

Aboonajmi, Jasem ;

Sharghi, Hashem ;

Aberi, Mahdi ;

Shiri, Pezhman .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (37) :5978-5984

[2] Iron Catalysis in Organic Synthesis [J].

Bauer, Ingmar ;

Knoelker, Hans-Joachim .

CHEMICAL REVIEWS, 2015, 115 (09) :3170-3387

[3] Copper-Catalyzed Aerobic Oxidative C(aryl)-OH Bond Functionalization of Catechols with Amines Affording Benzoxazoles [J].

Chen, Xiuling ;

Ji, Fangyan ;

Zhao, Yalei ;

Liu, Yanxi ;

Zhou, Yongbo ;

Chen, Tieqiao ;

Yin, Shuang-Feng .

ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (13) :2924-2930

[4] Nitrogen-containing compounds from Salvia miltiorrhiza [J].

Don, MJ ;

Shen, CC ;

Lin, YL ;

Syu, WJ ;

Ding, YH ;

Sun, CM .

JOURNAL OF NATURAL PRODUCTS, 2005, 68 (07) :1066-1070

[5] Imine allylation using 2-alkoxycarbonyl allylboronates as an expedient three-component reaction to polysubstituted α-exo-methylene-γ-lactams [J].

Elford, Tim G. ;

Hall, Dennis G. .

TETRAHEDRON LETTERS, 2008, 49 (49) :6995-6998

[6] Iron nitrate/TEMPO-catalyzed aerobic oxidative synthesis of quinazolinones from alcohols and 2-aminobenzamides with air as the oxidant [J].

Hu, Yongke ;

Chen, Lei ;

Li, Bindong .

RSC ADVANCES, 2016, 6 (69) :65196-65204

[7]

KOBAYASHI J, 1995, TETRAHEDRON LETT, V36, P5589

[8] Synthesis and evaluation of anticancer benzoxazoles and benzimidazoles related to UK-1 [J].

Kumar, D ;

Jacob, MR ;

Reynolds, MB ;

Kerwin, SM .

BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (12) :3997-4004

[9] One-Pot Syntheses of Pseudopteroxazoles from Pseudopterosins: A Rapid Route to Non-natural Congeners with Improved Antimicrobial Activity [J].

McCulloch, Malcolm W. B. ;

Berrue, Fabrice ;

Haltli, Brad ;

Kerr, Russell G. .

JOURNAL OF NATURAL PRODUCTS, 2011, 74 (10) :2250-2256

[10] OMS-2-Supported Cu Hydroxide-Catalyzed Benzoxazoles Synthesis from Catechols and Amines via Domino Oxidation Process at Room Temperature [J].

Meng, Xu ;

Wang, Yanmin ;

Wang, Yuanguang ;

Chen, Baohua ;

Jing, Zhenqiang ;

Chen, Gexin ;

Zhao, Peiqing .

JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (13) :6922-6931

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