L-Proline-catalyzed Knoevenagel condensation: A facile, green synthesis of (E)-ethyl 2-cyano-3-(1H-indol-3-yl)acrylates and (E)-3-(1H-indol-3-yl) acrylonitriles

Synthetic Communications

Volumn 42, Issue 12, 2012, Pages 1746-1759

  Venkatanarayana, M ^a   Dubey, P K ^a  

^a JAWAHARLAL NEHRU TECHNOLOGICAL UNIVERSITY   (India)

Author keywords

Alkylating agent; Ethyl cyanoacetate; Indole 3 aldehydes; Knoevenagel reaction; L Proline; PEG 600

Indexed keywords

ACETIC ACID DERIVATIVE; ACRYLIC ACID DERIVATIVE; ACRYLONITRILE; ALCOHOL; ALDEHYDE DERIVATIVE; DIMETHYL SULFATE; ORGANIC SOLVENT; PROLINE;

ARTICLE; CATALYSIS; CONTROLLED STUDY; KNOEVENAGEL CONDENSATION;

EID: 84857522732     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.543382     Document Type: Article

References (27)

1. 2 catalyst. Berichte 1898, 31, 2585-2596;
2. (b) Jones, G. Advanced organic chemistry: Reaction mechanisms. Org. React. 1967, 15, 204-599.
3. (a) Tietze, L. F.; Beifuss, U. In Comprehensive Organic Synthesis; B. M. Trost, I. Fleming, C. H. Heathcock (Eds.); Pergamon Press: Oxford, 1991; vol. 2, pp. 341-392;
4. (b) Bigi, F.; Chesini, L.; Magi, R.; Sartori, G. Montmorillonite KSF as an inorganic, water stable, and reusable catalyst for the Knoevenagel synthesis of coumarin-3-carboxylic acids. J. Org. Chem. 1999, 64, 1033-1035; (Pubitemid 29098037)
5. (c) Yu, N.; Armini, J. M.; German, M. W.; Hung, Z. Reactions of salicylaldehydes with alkyl cyanoacetates on the surface of solid catalysts: Syntheses of 4H-chromene derivatives. Tetrahedron Lett. 2000, 41, 6993-6996.
6. (a) Lyall, R.; Zilberstien, A.; Gazit, A.; Gilon, C.; Levitzki, A.; Schlessinger, J. Lewis acidic ionic liquids for the synthesis of electrophilic alkenes via the Knoevenagel condensation. J. Biol. Chem. 1989, 264, 14503-14509;
7. 2 catalyst. Cancer Res. 1989, 49, 2374-2378
8. (a) Allen, C. F. H.; Spangler, F. W. Electrophilic substitution of indoles catalyzed by triphenyl phosphonium perchlorate: Synthesis of 3-acetyl indoles and Bis-indolylmethane derivatives. Org. Synth. Coll. 1955, 3, 377-3379;
9. (b) Rand, L.; Swisher, J. V.; Cronin, C. J. Reactions catalyzed by potassium fluoride, III: The Knoevenagel reaction. J. Org. Chem. 1962, 27, 3505-3507.
10. (a) Rao, P. S.; Venkataratnam, R. V. Zinc chloride as a new catalyst for Knoevenagel condensation. Tetrahedron Lett. 1991, 32, 5821-5822;
11. (b) Prajpati, D.; Lekhok, K. C.; Sandhu, J. S.; Ghosh, A. C. Lithium bromide as a new catalyst for carbon-carbon bond formation in the solid state. J. Chem. Soc., Pekin. Trans. 1 1996, 959-960. (Pubitemid 126803612)
12. (a) Texier-Boullet, F.; Foucaud, A. Knoevenagel condensation catalysed by aluminium oxide. Tetrahedron Lett. 1982, 23, 4927-4928;
13. (b) Cabello, J. A.; Campelo, J. M.; Garia, A.; Luna, D.; Marinas, J. M. Knoevenagel condensation in the heterogeneous phase using AlP04-Al203 as a new catalyst. J. Org. Chem. 1984, 49, 5195-5197;
14. (c) Chalais, S.; Laszlo, P.; Mathy, A. Catalysis of the Knoevenagel condensation. Tetrahedron Lett. 1985, 26, 4453-4454;
15. (d) Laszlo, P. Catalysis of organic reactions by inorganic solids. Acc. Chem. Res. 1986, 19, 121-127.
16. (a) Reddy, T. I.; Varma, R. S. Rare-earth (RE) exchanged NaY zeolite-promoted Knoevenagel condensation. Tetrahedron Lett. 1997, 38, 1721-1724; (Pubitemid 27102313)
17. (b) Angeletti, E.; Canepa, C.; Martinetti, G.; Venturello, P. Amino groups immobilized on silica gel: An efficient and reusable heterogeneous catalyst for the Knoevenagel condensation. J. Chem. Soc. Perkin. Trans. 1 1989, 105-107;
18. (c) Rodriguez, I.; Iborra, S.; Corma, A.; Rey, F.; Jorda, J. L. The MCM-41-quaternary organic tetraalkylammonium hydroxide composites as strong and stable Brønsted base catalysts. Chem. Commun. 1999, 593-594. (Pubitemid 29158697)
19. (a) Dela Cruz, P.; Diez-Barra, E.; Loupy, A.; Langa, F. Silica gel-catalysed Knoevenagel condensation in dry media under microwave irradiation. Tetrahedron Lett. 1996, 37, 1113-1116; (Pubitemid 26052127)
20. 2-catalysed expedient synthesis of [E]-3-alkenoic acids in dry media. Tetrahedron Lett. 1999, 40, 2401-2404. (Pubitemid 29113159)
21. (a) Kloetstra, K. R.; Van Bekkum, H. Carbon-carbon bond formation on solid support: Synthesis of monoacyl piperazines by Knoevenagel-type condensation reactions. J. Chem. Soc. Chem. Commun. 1995, 1005-1006;
22. (b) Wada, S.; Suzuki, H. Calcite and fluorite as catalyst for the Knoevenagel condensation of malononitrile and methyl cyanoacetate under solvent-free conditions. Tetrahedron Lett. 2003, 44, 399-401; (Pubitemid 35449591)
23. (c) Sebti, S.; Smahi, A.; Solhy, A. Natural phosphate doped with potassium fluoride and modified with sodium nitrate: Efficient catalysts for the Knoevenagel condensation. Tetrahedron Lett. 2002, 43, 1813-1815. (Pubitemid 34175177)
24. (a) Su, C.; Chen, Z.-C.; Zheng, Q. G. Knoevenagel condensation doebner modification. Synthesis 2003, 555-559;
25. (b) Harjani, J. R.; Nara, S. J.; Salunkhe, M. M. Lewis acidic ionic liquids for the synthesis of electrophilic alkenes via the Knoevenagel condensation. Tetrahedron Lett. 2002, 43, 1127-1130. (Pubitemid 34119271)
26. (a) Dubey, P. K.; Balaji, B.; Venkatanarayana, M. Synthesis of N-alkyl/aryl derivatives of indole-3-aldehydes using TEBAC as phase transfer catalyst. Indian J. Heterocycl. Chem. 2006, 15, 205-208; (Pubitemid 44276889)
27. (b) Dubey, P. K.; Venkatanarayana, M. PEG-600: A facile and ecofriendly reaction medium for the synthesis of N-alkyl derivatives of indole-3- carboxyldehyde. Green Chem. Lett. Rev. 2010, 3(4), 257-261.