A Green, Inexpensive and Efficient Organocatalyzed Procedure for Aqueous Aldol Condensations

被引：13

作者：

Abaee, M. Saeed ^{[1
]}

Mojtahedi, Mohammad M. ^{[1
]}

Forghani, Soudabeh ^{[1
]}

Ghandchi, Nafiseh M. ^{[2
]}

Forouzani, Mehdi ^{[3
]}

Sharifi, Roholah ^{[1
]}

Chaharnazm, Behnam ^{[3
]}

机构：

[1] Chem & Chem Engn Res Ctr Iran, Fac Organ Chem & Nat Prod, Tehran 1496813151, Iran

[2] Islamic Azad Univ, Dept Chem, Tehran Cent Branch, Tehran 1467686831, Iran

[3] Payam Noor Univ, Dept Chem, Sari Ctr, Sari 4818858565, Iran

来源：

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY | 2009年 / 20卷 / 10期

关键词：

aldol condensation; aqueous conditions; organocatalyst; bisarylmethylidenes; chalcones; SUPERPARAMAGNETIC IRON-OXIDE; SOLVENT-FREE SYNTHESIS; ORGANIC-REACTIONS; FACILE SYNTHESIS; ONE-POT; CATALYST; ALDEHYDES; EPOXIDES; MEDIA; WATER;

D O I：

10.1590/S0103-50532009001000018

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A facile and general procedure is presented for diethylamine-catalyzed double crossed aldol condensation of cyclic ketones with various aromatic aldehydes under aqueous conditions. Excellent yields of 3,5-bisarylmethylidenes of homocyclic and heterocyclic ketones are achieved in a one-pot procedure. Furthermore, the methodology is efficiently applied to the synthesis of chalcones from their corresponding methyl ketones. In the majority of the cases studied, products precipitate from the reaction mixtures and the medium is recycled in subsequent several reactions without significant loss of activity.

引用

页码：1895 / S21

页数：27

共 46 条

[1] The first synthesis of bis(arylmethylidene)dioxan-5-ones: Potential scaffolds to access vicinal tricarbonyl derivatives [J].

Abaee, M. Saeed ;

Mojtahedi, Mohammad M. ;

Hamidi, Vahid ;

Mesbah, A. Wahid ;

Massa, Werner .

SYNTHESIS-STUTTGART, 2008, (13) :2122-2126

[2] Ultrasound promoted aminolysis of epoxides in aqueous media:: A rapid procedure with no pH adjustment for additive-free synthesis of β-aminoalcohols [J].

Abaee, M. Saeed ;

Hamidi, Vahid ;

Mojtahedi, Mohammad M. .

ULTRASONICS SONOCHEMISTRY, 2008, 15 (05) :823-827

[3] Additive-free thiolysis of epoxides in water:: A green and efficient regioselective pathway to β-hydroxy sulfides [J].

Abaee, M. Saeed ;

Mojtahedi, Mohammad M. ;

Abbasi, Hassan ;

Fatemi, Ensieh R. .

SYNTHETIC COMMUNICATIONS, 2008, 38 (02) :282-289

[4] Efficient synthesis of novel 3-substituted thiopyran-4-ones [J].

Abaee, M. Saeed ;

Mojtahedi, Mohammad M. ;

Zahedi, M. Mehdi ;

Sharifi, Roholah ;

Khavasi, Hamidreza .

SYNTHESIS-STUTTGART, 2007, (21) :3339-3344

[5]

Abaee MS, 2007, J HETEROCYCLIC CHEM, V44, P1497

[6] Amine-catalyzed aldol condensation in the presence of lithium perchlorate [J].

Arnold, A ;

Markert, M ;

Mahrwald, R .

SYNTHESIS-STUTTGART, 2006, (07) :1099-1102

[7] Dual-activation protocol for tandem cross-aldol condensation:: An easy and highly efficient synthesis of α,α′-bis(aryl/alkylmethylidene)ketones [J].

Bhagat, Srikant ;

Sharma, Ratnesh ;

Chakraborti, Asit K. .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 260 (1-2) :235-240

[8] Water in organocatalytic processes: Debunking the myths [J].

Blackmond, Donna G. ;

Armstrong, Alan ;

Coombe, Vyv ;

Wells, Andrew .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (21) :3798-3800

[9] Determining the geometries of transition states by use of antihydrophohic additives in water [J].

Breslow, R .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (07) :471-478

[10] HYDROPHOBIC EFFECTS ON SIMPLE ORGANIC-REACTIONS IN WATER [J].

BRESLOW, R .

ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (06) :159-164

← 1 2 3 4 5 →