Microwave-Assisted Mesoporous Molecular Sieve-Catalyzed Knoevenagel Condensation and Imine Formation Reactions under Solvent-free Conditions

Wonghil Chang; Byoung Joon Ahn

Journal of Industrial and Engineering Chemistry, Vol.10, No.4, 690-693, July, 2004

Wonghil Chang^†, and Byoung Joon Ahn¹

Department of Chemistry, Jeonju University, Jeonju 560-759, Korea
¹Department of Chemistry Education, Chonbuk National University, Jeonju 561-756, Korea

E-mail:

The reaction of benzaldehyde with ethyl cyanoacetate was carried out in the presence of the mesoporous molecular sieve M-AIKIT-1 (where M = Na, K, Rb, Cs) for 10 min. Imine formation reactions were also carried out under the same conditions. Microwave-assisted mesoporous molecular sieve-catalyzed Knoevenagel condensation and imine formation are efficient reactions under these solvent-free conditions. This method is an easy, rapid, and high-yielding one for conducting base-catalyzed condensation reactions.

Keywords:mesoporous molecular sieve;microwave irradiation;solvent-free;Knoevenagel condensation;imine formation

[References]

Izumi Y, Urabe K, Onaka M, Zeolite, Clay, and Heteropoly Acid in Organic Reactions, VCH, Weinheim (1992)
Wang J, Lin Z, Han SY, Eum M, Lee CW, J. Ind. Eng. Chem., 9(3), 281 (2003)
Corma A, Garcia H, J. Chem. Soc.-Dalton Trans., 1381 (2000)
Lee SK, Lee J, Joo J, Hyeon T, Ahn WS, Lee HI, Lee CH, Choi W, J. Ind. Eng. Chem., 9(1), 83 (2003)
Chang W, Shin J, Kim M, Ahn BJ, J. Ind. Eng. Chem., 7(1), 62 (2001)
Cadadick S, Tetrahedron, 51, 10403 (1995)
Strauss CR, Trainer RW, Aust. J. Chem., 48, 1665 (1995)
Hayes BL, Microwave Synthesis: Chemistry at the Speed of Light, CEM Publishing, Matthews, NC (2003)
Tanaka K, Solvent-free Organic Synthesis, John Wiley & Sons, New York, NY (2003)
Kaupp G, Naimi-Jamal MR, Schmeyers J, Tetrahedron, 59, 3753 (2003)
Michaud D, Hamelin J, Texier-Boullet F, Tetrahedron, 59, 3323 (2003)
Mogilaiah K, Reddy NV, Synth. Comm., 33, 73 (2003)
Mane AS, Chavan VP, Karale BK, Hangarge RV, Shingare MS, Synth. Comm., 32, 2633 (2002)
Michad D, Hamelin J, Texier-Boullet F, Toupet-L, Tetrahedron, 58, 5865 (2002)
Kaboudin B, Balakrishna M, Synth. Comm., 31, 2773 (2001)
Fildes D, Caignaert V, Villemin C, Faffres PA, Green Chem., 3, 52 (2001)
Corma A, Iborra S, Primo J, Rey F, Appl. Catal., 114, 215 (1994)
Price PM, Clark KH, Macquarrie DJ, J. Chem. Soc.-Dalton Trans., 101 (2000)
Rousselot I, Taviot-Gueho C, Besse JP, Int. J. Inorg. Mater., 165 (1999)
Choudary BM, Lakshmi Kantam LM, Kavita B, Reddy CV, Figuer F, Tetrahedron, 56, 9357 (2000)
Sugino T, Tanaka K, Chem. Lett., 110 (2000)
Correa WH, Scott JL, Green Chem., 3, 296 (2001)
Bogdal D, J. Chem. Res.(S), 468 (1998)
Kloetstra KR, van Bekkum H, J. Chem. Soc.-Chem. Commun., 1005 (1995)
Macquarrie DJ, Jackson DB, J. Chem. Soc.-Chem. Commun., 1781 (1997)
Varma RS, Dahiya R, Kumar S, Tetrahedron Lett., 38, 2039 (1997)

[Referenced By]

[1] Izumi Y, Urabe K, Onaka M, Zeolite, Clay, and Heteropoly Acid in Organic Reactions, VCH, Weinheim (1992)

[2] Wang J, Lin Z, Han SY, Eum M, Lee CW, J. Ind. Eng. Chem., 9(3), 281 (2003)

[3] Corma A, Garcia H, J. Chem. Soc.-Dalton Trans., 1381 (2000)

[4] Lee SK, Lee J, Joo J, Hyeon T, Ahn WS, Lee HI, Lee CH, Choi W, J. Ind. Eng. Chem., 9(1), 83 (2003)

[5] Chang W, Shin J, Kim M, Ahn BJ, J. Ind. Eng. Chem., 7(1), 62 (2001)

[6] Cadadick S, Tetrahedron, 51, 10403 (1995)

[7] Strauss CR, Trainer RW, Aust. J. Chem., 48, 1665 (1995)

[8] Hayes BL, Microwave Synthesis: Chemistry at the Speed of Light, CEM Publishing, Matthews, NC (2003)

[9] Tanaka K, Solvent-free Organic Synthesis, John Wiley & Sons, New York, NY (2003)

[10] Kaupp G, Naimi-Jamal MR, Schmeyers J, Tetrahedron, 59, 3753 (2003)

[11] Michaud D, Hamelin J, Texier-Boullet F, Tetrahedron, 59, 3323 (2003)

[12] Mogilaiah K, Reddy NV, Synth. Comm., 33, 73 (2003)

[13] Mane AS, Chavan VP, Karale BK, Hangarge RV, Shingare MS, Synth. Comm., 32, 2633 (2002)

[14] Michad D, Hamelin J, Texier-Boullet F, Toupet-L, Tetrahedron, 58, 5865 (2002)

[15] Kaboudin B, Balakrishna M, Synth. Comm., 31, 2773 (2001)

[16] Fildes D, Caignaert V, Villemin C, Faffres PA, Green Chem., 3, 52 (2001)

[17] Corma A, Iborra S, Primo J, Rey F, Appl. Catal., 114, 215 (1994)

[18] Price PM, Clark KH, Macquarrie DJ, J. Chem. Soc.-Dalton Trans., 101 (2000)

[19] Rousselot I, Taviot-Gueho C, Besse JP, Int. J. Inorg. Mater., 165 (1999)

[20] Choudary BM, Lakshmi Kantam LM, Kavita B, Reddy CV, Figuer F, Tetrahedron, 56, 9357 (2000)

[21] Sugino T, Tanaka K, Chem. Lett., 110 (2000)

[22] Correa WH, Scott JL, Green Chem., 3, 296 (2001)

[23] Bogdal D, J. Chem. Res.(S), 468 (1998)

[24] Kloetstra KR, van Bekkum H, J. Chem. Soc.-Chem. Commun., 1005 (1995)

[25] Macquarrie DJ, Jackson DB, J. Chem. Soc.-Chem. Commun., 1781 (1997)

[26] Varma RS, Dahiya R, Kumar S, Tetrahedron Lett., 38, 2039 (1997)