A New and Efficient Procedure for Friedlander Synthesis of Quinolines in Low Melting Tartaric Acid-Urea Mixtures

被引：25

作者：

Ma, Fei-Ping ^{[1
]}

Cheng, Gui-Tian ^{[2
]}

He, Zhi-Guo ^{[3
]}

Zhang, Zhan-Hui ^{[1
]}

机构：

[1] Hebei Normal Univ, Coll Chem & Mat Sci, Shijiazhuang 050024, Peoples R China

[2] Hebei Chem & Pharmaceut Vocat Technol Coll, Shijiazhuang 050026, Peoples R China

[3] Hebei Normal Univ, Coll Resources & Environm, Shijiazhuang 050024, Peoples R China

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 2012年 / 65卷 / 04期

基金：

中国国家自然科学基金;

关键词：

SOLVENT-FREE CONDITIONS; MAGNETIC FE3O4 NANOPARTICLES; SALT MIXTURES; SUBSTITUTED QUINOLINES; HYDROGEN SULFATE; IONIC LIQUID; CATALYST; DERIVATIVES; WATER; ANNULATION;

D O I：

10.1071/CH12025

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A general, efficient and green method for the synthesis of quinoline derivatives via the Friedlander heteroannulation reaction of 2-aminoaryl ketones and alpha-methylene ketones has been developed, employing low melting mixtures of L-(+)-tartaric acid and urea derivatives as an inexpensive, non-toxic, easily biodegradable reaction medium. The melt acts as both the reaction medium and catalyst, furnishing quinolines in high to excellent yields.

引用

页码：409 / 416

页数：8

共 66 条

[1] Green materials synthesis with supercritical water [J].

Adschiri, Tadafumi ;

Lee, Youn-Woo ;

Goto, Motonobu ;

Takami, Seiichi .

GREEN CHEMISTRY, 2011, 13 (06) :1380-1390

[2] Sulfonic Acid Functionalized Ionic Liquid in Combinatorial Approach, a Recyclable and Water Tolerant-Acidic Catalyst for One-Pot Friedlander Quinoline Synthesis [J].

Akbari, Jafar ;

Heydari, Akbar ;

Kalhor, Hamid Reza ;

Kohan, Sirus Azizian .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (01) :137-140

[3] An efficient catalytic method for the Friedlander annulation mediated by peptide coupling agent propylphosphonic anhydride (T3P®) [J].

Augustine, John Kallikat ;

Bombrun, Agnes ;

Venkatachaliah, Srinivasa .

TETRAHEDRON LETTERS, 2011, 52 (50) :6814-6818

[4] A microwave-assisted, facile, regioselective Friedlander synthesis and antitubercular evaluation of 2,9-diaryl-2,3-dihydrothieno-[3,2-b]quinolines [J].

Balamurugan, Kamaraj ;

Jeyachandran, Veerappan ;

Perumal, Subbu ;

Manjashetty, Thimmappa H. ;

Yogeeswari, Perumal ;

Sriram, Dharmarajan .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (02) :682-688

[5] o-Benzenedisulfonimide as a reusable Bronsted acid catalyst for an efficient and facile synthesis of quinolines via Friedlander annulation [J].

Barber, Margherita ;

Bazzi, Stefano ;

Cadamuro, Silvano ;

Dughera, Stefano .

TETRAHEDRON LETTERS, 2010, 51 (17) :2342-2344

[6] Diversity-Oriented Synthesis of Quinolines via Friedlander Annulation Reaction under Mild Catalytic Conditions [J].

Bose, D. Subhas ;

Idrees, Mohd. ;

Jakka, N. M. ;

Rao, J. Venkateswara .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (01) :100-110

[7] Water: Nature's Reaction Enforcer-Comparative Effects for Organic Synthesis "In-Water" and "On-Water" [J].

Butler, Richard N. ;

Coyne, Anthony G. .

CHEMICAL REVIEWS, 2010, 110 (10) :6302-6337

[8] Quinoline tricyclic derivatives. Design, synthesis and evaluation of the antiviral activity of three new classes of RNA-dependent RNA polymerase inhibitors [J].

Carta, Antonio ;

Briguglio, Irene ;

Piras, Sandra ;

Corona, Paola ;

Boatto, Giampiero ;

Nieddu, Maria ;

Giunchedi, Paolo ;

Marongiu, Maria Elena ;

Giliberti, Gabriele ;

Iuliano, Filippo ;

Blois, Sylvain ;

Ibba, Cristina ;

Busonera, Bernardetta ;

La Colla, Paolo .

BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (23) :7070-7084

[9] Efficient Synthesis of 2,3,4-Trisubstituted Quinolines via Friedlander Annulation with Nanoporous Cage-Type Aluminosilicate AlKIT-5 Catalyst [J].

Chauhan, S. ;

Chakravarti, R. ;

Zaidi, S. M. J. ;

Al-Deyab, Salem S. ;

Reddy, B. V. Subba ;

Vinu, A. .

SYNLETT, 2010, (17) :2597-2600

[10] Synthesis, Characterization, Antibacterial and Antifungal Activity of 2-(Aryl)-3-(3-((8-hydroxyquinolin-5-yl)diazenyl)phenyl)thiazolidin-4-ones [J].

Chopde, Himani N. ;

Pagadala, Ramakanth ;

Meshram, Jyotsna S. ;

Jetti, Venkateshwarlu .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2011, 48 (06) :1323-1328

← 1 2 3 4 5 6 7 →