How to cite this paper
Javanshir, S., Mojtahedi, M & Eslami, J. (2014). A Highly Efficient Method for Synthesis of Bisarylmethylidenes of Cyclic Ketones in [BMIm]Cl/NaOH System as New and Recyclable Catalyst.Current Chemistry Letters, 3(2), 63-70.
Refrences
1. Arsanious, M. H. N.; El-Din, N. K.; Boulos, L. S. (2009) Synthesis of new benzoxaphosphole derivatives from the reaction of dialkylphosphonates and trisdialkylaminophosphines with 2,6-bis(benzylidene)cyclohexanones. Phosphorus, Sulfur Silicon Relat. Elem., 184, 2813-2826.
2. (a) Kumar, R. R.; Loganayaki, B.; Perumal, S. (2009) Sequential 1,3-dipolar cycloadditions in the synthesis of novel tri-spiro cyclohexanones and piperidin-4-ones. Synth. Commun., 39, 3197 - 3216; (b) Singh, N.; Pandey, J.; Yadav, A.; Chaturvedi, V.; Bhatnagar, S.; Gaikwad, A. N.; Sinha, S. K.; Kumar, A.; Shukla, P. K.; Tripathi, R. P. (2009) A facile synthesis of ?,? & apos; -(E,E)-bis(benzylidene)-cycloalkanones and their antitubercular evaluations. Eur. J. Med. Chem., 44, 1705-1709.
3. (a) Modzelewska, A.; Pettit, C.; Achanta, G.; Davidson, N. E.; Huang, P.; Khan, S. R. (2006) Anticancer activities of novel chalcone and bis-chalcone derivatives. Bioorg. Med. Chem., 14, 3491-3495; (b) Dimmock, J. R.; Kumar, P.; Nazarali, A. J.; Motaganahalli, N. L.; Kowalchuk, T. P.; Beazely, M. A.; Wilson Quail, J.; Oloo, E. O.; Allen, T. M.; Szydlowski, J.; DeClercq, E.; Balzarini, J. (2000) Cytotoxic 2,6-bis(arylidene)cyclohexanones and related compounds. Eur. J. Med. Chem., 35, 967-977; (c) Dimmock, J. R.; Das, U.; Gul, H. I.; Kawase, M.; Sakagami, H.; Bar?th, Z.; Ocsovsky, I.; Moln?r, J. (2005) 3-Arylidene-1-(4-nitrophenylmethylene)-3,4-dihydro-1H-naphthalen-2-ones and related compounds displaying selective toxicity and reversal of multidrug resistance in neoplastic cells. Bioorg. Med. Chem. Lett., 15, 1633-1636; (d) Ciufolini, M. A.; Byrne, N. E. (1991) The total synthesis of cystodytins. J. Am. Chem. Soc., 113, 8016-8024; (e) Dimmock, J. R. A.; Padmanilayam, M. P.; Zello, G. A.; Nienaber, K. H.; Allen, T. M.; Santos, C. L.; De Clercq, E.; Balzarini, J.; Manavathu, E. K.; Stables, J. P. (2003) Eur. J. Med. Chem., 38, 169; (f) Dimmock, J. R.; Padmanilayam, M. P.; Zello, G. A.; Nienaber, K. H.; Allen, T. M.; Santos, C. L.; De Clercq, E.; Balzarini, J.; Manavathu, E. K.; Stables, J. P. (2003) Cytotoxic analogues of 2,6-bis(arylidene)cyclohexanones. Eur. J. Med. Chem., 38, 169-177.
4. (a) Weber, W. M.; Hunsaker, L. A.; Abcouwer, S. F.; Deck, L. M.; Vander Jagt, D. L. (2005) Anti-oxidant activities of curcumin and related enones. Bioorg. Med. Chem. , 13, 3811-3820; (b) El-Gazzar, A. B. A.; Hafez, H. N.; Nawwar, G. A. M. (2009) New acyclic nucleosides analogues as potential analgesic, anti-inflammatory, anti-oxidant and anti-microbial derived from pyrimido[4,5-b]quinolines. Eur. J. Med. Chem., 44, 1427-1436.
5. (a) Nasr, M. N. A.; Said, S. A. (2003) Novel 3,3a,4,5,6,7-Hexahydroindazole and arylthiazolylpyrazoline derivatives as anti-inflammatory agents. Arch. Pharm. , 336, 551-559; (b) Abu-Hashem, A. A.; Gouda, M. A.; Badria, F. A. (2010) Synthesis of some new pyrimido[2 & apos; ,1 & apos; :2,3]thiazolo[4,5-b]quinoxaline derivatives as anti-inflammatory and analgesic agents. Eur. J. Med. Chem., 45, 1976-1981; (c) Rovnyak, G.; Shu, V.; Schwartz, J. (1981) Tricyclic thiazolo[3,2-a]thiapyrano[4,3-d]pyrimidines and related analogs as potential anti-inflammatory agents. J. Heterocycl. Chem., 18, 327-331.
6. (a) Robinson, T. P.; Ehlers, T.; Hubbard, I. V. R. B.; Bai, X.; Arbiser, J. L.; Goldsmith, D. J.; Bowen, J. P. (2003) Design, synthesis, and biological evaluation of angiogenesis inhibitors: aromatic enone and dienone analogues of curcumin. Bioorg. Med. Chem. Lett., 13, 115-117; (b) Robinson, T. P.; Hubbard Iv, R. B.; Ehlers, T. J.; Arbiser, J. L.; Goldsmith, D. J.; Bowen, J. P. (2005) Synthesis and biological evaluation of aromatic enones related to curcumin. Bioorg. Med. Chem. , 13, 4007-4013.
7. (a) Artico, M.; Di Santo, R.; Costi, R.; Novellino, E.; Greco, G.; Massa, S.; Tramontano, E.; Marongiu, M. E.; De Montis, A.; La Colla, P. (1998). Geometrically and conformationally restrained cinnamoyl compounds as inhibitors of HIV-1 Integrase: synthesis, biological evaluation, and Molecular Modeling. J. Med. Chem., 41, 3948-3960; (b) Costi, R.; Santo, R. D.; Artico, M.; Massa, S.; Rango, R.; Laddo, R.; Colla, M. L.; Tramontano, E.; Colla, P. L.; Pani, A. (2004) 2,6-Bis(3,4,5-trihydroxybenzylydene) derivatives of cyclohexanone: novel potent HIV-1 integrase inhibitors that prevent HIV-1 multiplication in cell-based assays. Bioorg. Med. Chem, 12, 199.
8. Amr, A. E.-G. E.; Sayed, H. H.; Abdulla, M. M. (2005) Synthesis and reactions of some new substituted pyridine and pyrimidine derivatives as analgesic, anticonvulsant and antiparkinsonian agents. Arch. Pharm., 338, 433-440.
9. Ogawa, M.; Ishii, Y.; Nakano, T.; Irifune, S. (1988) Jpn. Kohai Tokkyo JP 63192446 A2 ; Chem. Abstr. 63 (1988) 238034.
10. Kawamata, J.; Inoue, K.; Inabe, T.; Kiguchi, M.; Kato, M.; Taniguchi, Y. (1996). Large second-harmonic generation coefficients of bis(benzylidine) cycloalkanones estimated by the second-harmonic wave generated with the evanescent wave technique. Chem. Phys. Lett., 249, 29-34.
11. Gangadhara; Kishore, K. (1995) Synthesis and characterization of photo-crosslinkable main-chain liquid-crystalline polymers containing bis(benzylidene)cycloalkanone units. Polym. Int., 36, 1903-1910.
12. Shibuguchi, T.; Mihara, H.; Kuramochi, A.; Sakuraba, S.; Ohshima, T.; Shibasaki, M. (2006). Short synthesis of (+)-cylindricine C by using a catalytic asymmetric michael reaction with a two-center organocatalyst. Angew. Chem. Int. Ed., 45, 4635-4637.
13. Amr, A. E.-G. E.; Sayed, H. H.; Abdulla, M. M. (2005) Synthesis and Reactions of Some New Substituted Pyridine and Pyrimidine Derivatives as Analgesic, Anticonvulsant and Antiparkinsonian Agents. Archiv der Pharmazie, 338, 433-440.
14. Hathaway, B. A. (1987) An aldol condensation experiment using a number of aldehydes and ketones. J. Chem. Educ., 64, 367-368.
15. (a) Irie, K.; Watanabe, K. (1980) Bull. Chem. Soc. Jpn., 53, 1366; (b) Nakano, T.; Migita, T. (1993). A convenient synthesis of ?,? & apos; -bis(substitutedbenzylidene)cycloalkanones. Chem. Lett., 22, 2157-2158.
16. Oayama, Y.; Tanaka, Y.; Yoshida, Y.; Toi, H.; Ogoshi, H. (1987) Catalytic reactions of metalloporphyrins.: II. Activation and catalytic aldol condensation of ketone with rhodium(III)-porphyrin perchlorate under neutral and mild conditions. J. Organomet. Chem. , 329, 251-266.
17. Iranpoor, N.; Kazemi, F. (1998) RuCI3 catalyses aldol condensations of aldehydes and ketones Tetrahedron, 54, 9475.
18. (a) Bao, W.; Zhang, Y.; Ying, T. (1996) A facile route to synthesize ?,? & apos; -bis(substituted-benzylidene) cycloalkanones promoted by SmI3. Synth. Commun., 26, 503-507; (b) Li, Z.; Zhang, Y.; Li, Q. (2000) Samarium (III) iodide promoted preparation of, ?,? & apos; -bis (substituted benzylidene)cyclohexanones from benzaldehydes and cyclohexanone. J. Chem. Res., Synop., 580-581.
19. Huang, D. F.; Wang, J. X.; Hu, Y. L. (2003) A new solvent-free synthesis of ?,??-dibenzylidenecycloalkanones from acetals with cycloalkanones under microwave irradiation. Chin. Chem. Lett., 14, 333.
20. Zhang, X.; Fan, X.; Niu, H.; Wang, J. (2003) An ionic liquid as a recyclable medium for the green preparation of ?,? & apos; -bis (substituted benzylidene)cycloalkanones catalyzed by FeCl3.6H2O. Green Chem., 5, 267-269.
21. Abaee, M. S.; Mojtahedi, M. M.; Zahedi, M. M.; Sharifi, R.; Mesbah, A. W.; Massa, W. (2007) Synthesis and structural elucidation of novel bisarylmethylidenes of cyclic enones. Synth. Commun., 37, 2949-2957.
22. Salehi, P.; Khodaei, M. M.; Zolfigol, M. A.; Keyvan, A. (2002) Solvent-free crossed aldol condensation of ketones with aromatic aldehydes mediated by magnesium hydrogensulfate. Monatsh. Chem., 133, 1291-1295.23. Zhu, Y.; Pan, Y. (2004) A new Lewis acid system palladium/TMSCl for catalytic aldol condensation of aldehydes with ketones. Chem. Lett. , 33, 668-669.
23. (a) Abaee, M. S.; Mojtahedi, M. M.; Sharifi, R.; Zahedi, M. M.; Abbasi, H.; Tabar-Heidar, K. (2006) Facile synthesis of bis(arylmethylidene)cycloalkanones mediated by lithium perchlorate under solvent-free conditions. J. Iran Chem. Soc., 3, 293-296; (b) Arnold, A.; Markert, M.; Mahrwald, R. (2006) Amine-catalyzed aldol condensation in the Presence of lithium perchlorate. Synthesis, 7, 1099-1102.
24. Wang, L.; Sheng, J.; Tian, H.; Han, J.; Fan, Z.; Qian, C. (2004) A convenient synthesis of ?,? & apos; -bis(substituted benzylidene)cycloalkanones catalyzed by Yb(OTf)3 under solvent-free conditions. Synthesis, 18, 3060-3064.
25. Yi, W. B.; Cai, C. (2005) Aldol condensations of aldehydes and ketones catalyzed by rare earth(III) perfluorooctane sulfonates in fluorous solvents. J. Fluorine Chem., 126, 1553-1558.
26. (a) Deng, G.; Ren, T. (2003) Indium trichloride catalyzes Aldol-condensations of aldehydes and ketones. Synth. Commun., 33, 2995-3001; (b) Hu, X.; Fan, X.; Zhang, X.; Wang, J. (2004). InCl3.4H2O/TMSCl-catalysed aldol reaction of aromatic aldehydes with cycloalkanones in ionic liquid medium. J. Chem. Res., 684-686.
27. Li, J.; Su, W.; Li, N. (2005) Copper triflate–catalyzed Cross-aldol condensation: a facile synthesis of ?,? & apos; -bis(substituted benzylidene) cycloalkanones. Synth. Commun., 35, 3037-3043.
28. Nakano, T.; Irfune, S.; Umano, S.; Inada, A.; Ishii, Y.; Ogawa, M. (1987) Cross-condensation reactions of cycloalkanones with aldehydes and primary alcohols under the influence of zirconocene complexes J. Org. Chem., 52, 2239- 2244.
29. Kelleher, R. G.; McKervey, M. A.; Vibuljan, P. (1980) Lithium iodide-promoted aldol condensation reactions. J. Chem. Soc., Chem. Commun., 486-488.
30. (a) Zhou, J. F.; Sun, X. J.; Zhu, F. X.; Li, Y. L.; Gong, G.-X. (2008) A facile synthesis of 5-arylidene-2-imino-4-thiazolidinones under microwave irradiation. Synth. Commun., 38, 4182-4187; (b) Motiur Rahman, A. F. M.; Jeong, B.-S.; Kim, D. H.; Park, J. K.; Lee, E. S.; Jahng, Y. (2007) A facile synthesis of ?,? & apos; -bis(substituted-benzylidene) cycloalkanones and substituted-benzylidene heteroaromatics: utility of NaOAc as a catalyst for aldol-type reaction. Tetrahedron, 63, 2426-2431.
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38. Ranu, B. C.; Banerjee, S. (2005) Ionic liquid as catalyst and reaction medium. the dramatic influence of a task-specific ionic liquid, [bmIm]OH, in Michael addition of active methylene compounds to conjugated ketones, carboxylic esters, and nitriles. Org. Lett., 7, 3049-3052.
39. Guo, K.; Thompson, M. J.; Chen, B. (2009) Exploring catalyst and solvent effects in the multicomponent synthesis of pyridine-3,5-dicarbonitriles. J. Org. Chem., 74, 6999-7006.
40. Dupont, J.; Consorti, C. S.; Suarez, P. A. Z.; De Souza, R. F. (2004) Preparation of 1-butyl-3-methyl imidazolium-based room temperature ionic liquids. Organic Syntheses, Coll.. 10, 184-187.
2. (a) Kumar, R. R.; Loganayaki, B.; Perumal, S. (2009) Sequential 1,3-dipolar cycloadditions in the synthesis of novel tri-spiro cyclohexanones and piperidin-4-ones. Synth. Commun., 39, 3197 - 3216; (b) Singh, N.; Pandey, J.; Yadav, A.; Chaturvedi, V.; Bhatnagar, S.; Gaikwad, A. N.; Sinha, S. K.; Kumar, A.; Shukla, P. K.; Tripathi, R. P. (2009) A facile synthesis of ?,? & apos; -(E,E)-bis(benzylidene)-cycloalkanones and their antitubercular evaluations. Eur. J. Med. Chem., 44, 1705-1709.
3. (a) Modzelewska, A.; Pettit, C.; Achanta, G.; Davidson, N. E.; Huang, P.; Khan, S. R. (2006) Anticancer activities of novel chalcone and bis-chalcone derivatives. Bioorg. Med. Chem., 14, 3491-3495; (b) Dimmock, J. R.; Kumar, P.; Nazarali, A. J.; Motaganahalli, N. L.; Kowalchuk, T. P.; Beazely, M. A.; Wilson Quail, J.; Oloo, E. O.; Allen, T. M.; Szydlowski, J.; DeClercq, E.; Balzarini, J. (2000) Cytotoxic 2,6-bis(arylidene)cyclohexanones and related compounds. Eur. J. Med. Chem., 35, 967-977; (c) Dimmock, J. R.; Das, U.; Gul, H. I.; Kawase, M.; Sakagami, H.; Bar?th, Z.; Ocsovsky, I.; Moln?r, J. (2005) 3-Arylidene-1-(4-nitrophenylmethylene)-3,4-dihydro-1H-naphthalen-2-ones and related compounds displaying selective toxicity and reversal of multidrug resistance in neoplastic cells. Bioorg. Med. Chem. Lett., 15, 1633-1636; (d) Ciufolini, M. A.; Byrne, N. E. (1991) The total synthesis of cystodytins. J. Am. Chem. Soc., 113, 8016-8024; (e) Dimmock, J. R. A.; Padmanilayam, M. P.; Zello, G. A.; Nienaber, K. H.; Allen, T. M.; Santos, C. L.; De Clercq, E.; Balzarini, J.; Manavathu, E. K.; Stables, J. P. (2003) Eur. J. Med. Chem., 38, 169; (f) Dimmock, J. R.; Padmanilayam, M. P.; Zello, G. A.; Nienaber, K. H.; Allen, T. M.; Santos, C. L.; De Clercq, E.; Balzarini, J.; Manavathu, E. K.; Stables, J. P. (2003) Cytotoxic analogues of 2,6-bis(arylidene)cyclohexanones. Eur. J. Med. Chem., 38, 169-177.
4. (a) Weber, W. M.; Hunsaker, L. A.; Abcouwer, S. F.; Deck, L. M.; Vander Jagt, D. L. (2005) Anti-oxidant activities of curcumin and related enones. Bioorg. Med. Chem. , 13, 3811-3820; (b) El-Gazzar, A. B. A.; Hafez, H. N.; Nawwar, G. A. M. (2009) New acyclic nucleosides analogues as potential analgesic, anti-inflammatory, anti-oxidant and anti-microbial derived from pyrimido[4,5-b]quinolines. Eur. J. Med. Chem., 44, 1427-1436.
5. (a) Nasr, M. N. A.; Said, S. A. (2003) Novel 3,3a,4,5,6,7-Hexahydroindazole and arylthiazolylpyrazoline derivatives as anti-inflammatory agents. Arch. Pharm. , 336, 551-559; (b) Abu-Hashem, A. A.; Gouda, M. A.; Badria, F. A. (2010) Synthesis of some new pyrimido[2 & apos; ,1 & apos; :2,3]thiazolo[4,5-b]quinoxaline derivatives as anti-inflammatory and analgesic agents. Eur. J. Med. Chem., 45, 1976-1981; (c) Rovnyak, G.; Shu, V.; Schwartz, J. (1981) Tricyclic thiazolo[3,2-a]thiapyrano[4,3-d]pyrimidines and related analogs as potential anti-inflammatory agents. J. Heterocycl. Chem., 18, 327-331.
6. (a) Robinson, T. P.; Ehlers, T.; Hubbard, I. V. R. B.; Bai, X.; Arbiser, J. L.; Goldsmith, D. J.; Bowen, J. P. (2003) Design, synthesis, and biological evaluation of angiogenesis inhibitors: aromatic enone and dienone analogues of curcumin. Bioorg. Med. Chem. Lett., 13, 115-117; (b) Robinson, T. P.; Hubbard Iv, R. B.; Ehlers, T. J.; Arbiser, J. L.; Goldsmith, D. J.; Bowen, J. P. (2005) Synthesis and biological evaluation of aromatic enones related to curcumin. Bioorg. Med. Chem. , 13, 4007-4013.
7. (a) Artico, M.; Di Santo, R.; Costi, R.; Novellino, E.; Greco, G.; Massa, S.; Tramontano, E.; Marongiu, M. E.; De Montis, A.; La Colla, P. (1998). Geometrically and conformationally restrained cinnamoyl compounds as inhibitors of HIV-1 Integrase: synthesis, biological evaluation, and Molecular Modeling. J. Med. Chem., 41, 3948-3960; (b) Costi, R.; Santo, R. D.; Artico, M.; Massa, S.; Rango, R.; Laddo, R.; Colla, M. L.; Tramontano, E.; Colla, P. L.; Pani, A. (2004) 2,6-Bis(3,4,5-trihydroxybenzylydene) derivatives of cyclohexanone: novel potent HIV-1 integrase inhibitors that prevent HIV-1 multiplication in cell-based assays. Bioorg. Med. Chem, 12, 199.
8. Amr, A. E.-G. E.; Sayed, H. H.; Abdulla, M. M. (2005) Synthesis and reactions of some new substituted pyridine and pyrimidine derivatives as analgesic, anticonvulsant and antiparkinsonian agents. Arch. Pharm., 338, 433-440.
9. Ogawa, M.; Ishii, Y.; Nakano, T.; Irifune, S. (1988) Jpn. Kohai Tokkyo JP 63192446 A2 ; Chem. Abstr. 63 (1988) 238034.
10. Kawamata, J.; Inoue, K.; Inabe, T.; Kiguchi, M.; Kato, M.; Taniguchi, Y. (1996). Large second-harmonic generation coefficients of bis(benzylidine) cycloalkanones estimated by the second-harmonic wave generated with the evanescent wave technique. Chem. Phys. Lett., 249, 29-34.
11. Gangadhara; Kishore, K. (1995) Synthesis and characterization of photo-crosslinkable main-chain liquid-crystalline polymers containing bis(benzylidene)cycloalkanone units. Polym. Int., 36, 1903-1910.
12. Shibuguchi, T.; Mihara, H.; Kuramochi, A.; Sakuraba, S.; Ohshima, T.; Shibasaki, M. (2006). Short synthesis of (+)-cylindricine C by using a catalytic asymmetric michael reaction with a two-center organocatalyst. Angew. Chem. Int. Ed., 45, 4635-4637.
13. Amr, A. E.-G. E.; Sayed, H. H.; Abdulla, M. M. (2005) Synthesis and Reactions of Some New Substituted Pyridine and Pyrimidine Derivatives as Analgesic, Anticonvulsant and Antiparkinsonian Agents. Archiv der Pharmazie, 338, 433-440.
14. Hathaway, B. A. (1987) An aldol condensation experiment using a number of aldehydes and ketones. J. Chem. Educ., 64, 367-368.
15. (a) Irie, K.; Watanabe, K. (1980) Bull. Chem. Soc. Jpn., 53, 1366; (b) Nakano, T.; Migita, T. (1993). A convenient synthesis of ?,? & apos; -bis(substitutedbenzylidene)cycloalkanones. Chem. Lett., 22, 2157-2158.
16. Oayama, Y.; Tanaka, Y.; Yoshida, Y.; Toi, H.; Ogoshi, H. (1987) Catalytic reactions of metalloporphyrins.: II. Activation and catalytic aldol condensation of ketone with rhodium(III)-porphyrin perchlorate under neutral and mild conditions. J. Organomet. Chem. , 329, 251-266.
17. Iranpoor, N.; Kazemi, F. (1998) RuCI3 catalyses aldol condensations of aldehydes and ketones Tetrahedron, 54, 9475.
18. (a) Bao, W.; Zhang, Y.; Ying, T. (1996) A facile route to synthesize ?,? & apos; -bis(substituted-benzylidene) cycloalkanones promoted by SmI3. Synth. Commun., 26, 503-507; (b) Li, Z.; Zhang, Y.; Li, Q. (2000) Samarium (III) iodide promoted preparation of, ?,? & apos; -bis (substituted benzylidene)cyclohexanones from benzaldehydes and cyclohexanone. J. Chem. Res., Synop., 580-581.
19. Huang, D. F.; Wang, J. X.; Hu, Y. L. (2003) A new solvent-free synthesis of ?,??-dibenzylidenecycloalkanones from acetals with cycloalkanones under microwave irradiation. Chin. Chem. Lett., 14, 333.
20. Zhang, X.; Fan, X.; Niu, H.; Wang, J. (2003) An ionic liquid as a recyclable medium for the green preparation of ?,? & apos; -bis (substituted benzylidene)cycloalkanones catalyzed by FeCl3.6H2O. Green Chem., 5, 267-269.
21. Abaee, M. S.; Mojtahedi, M. M.; Zahedi, M. M.; Sharifi, R.; Mesbah, A. W.; Massa, W. (2007) Synthesis and structural elucidation of novel bisarylmethylidenes of cyclic enones. Synth. Commun., 37, 2949-2957.
22. Salehi, P.; Khodaei, M. M.; Zolfigol, M. A.; Keyvan, A. (2002) Solvent-free crossed aldol condensation of ketones with aromatic aldehydes mediated by magnesium hydrogensulfate. Monatsh. Chem., 133, 1291-1295.23. Zhu, Y.; Pan, Y. (2004) A new Lewis acid system palladium/TMSCl for catalytic aldol condensation of aldehydes with ketones. Chem. Lett. , 33, 668-669.
23. (a) Abaee, M. S.; Mojtahedi, M. M.; Sharifi, R.; Zahedi, M. M.; Abbasi, H.; Tabar-Heidar, K. (2006) Facile synthesis of bis(arylmethylidene)cycloalkanones mediated by lithium perchlorate under solvent-free conditions. J. Iran Chem. Soc., 3, 293-296; (b) Arnold, A.; Markert, M.; Mahrwald, R. (2006) Amine-catalyzed aldol condensation in the Presence of lithium perchlorate. Synthesis, 7, 1099-1102.
24. Wang, L.; Sheng, J.; Tian, H.; Han, J.; Fan, Z.; Qian, C. (2004) A convenient synthesis of ?,? & apos; -bis(substituted benzylidene)cycloalkanones catalyzed by Yb(OTf)3 under solvent-free conditions. Synthesis, 18, 3060-3064.
25. Yi, W. B.; Cai, C. (2005) Aldol condensations of aldehydes and ketones catalyzed by rare earth(III) perfluorooctane sulfonates in fluorous solvents. J. Fluorine Chem., 126, 1553-1558.
26. (a) Deng, G.; Ren, T. (2003) Indium trichloride catalyzes Aldol-condensations of aldehydes and ketones. Synth. Commun., 33, 2995-3001; (b) Hu, X.; Fan, X.; Zhang, X.; Wang, J. (2004). InCl3.4H2O/TMSCl-catalysed aldol reaction of aromatic aldehydes with cycloalkanones in ionic liquid medium. J. Chem. Res., 684-686.
27. Li, J.; Su, W.; Li, N. (2005) Copper triflate–catalyzed Cross-aldol condensation: a facile synthesis of ?,? & apos; -bis(substituted benzylidene) cycloalkanones. Synth. Commun., 35, 3037-3043.
28. Nakano, T.; Irfune, S.; Umano, S.; Inada, A.; Ishii, Y.; Ogawa, M. (1987) Cross-condensation reactions of cycloalkanones with aldehydes and primary alcohols under the influence of zirconocene complexes J. Org. Chem., 52, 2239- 2244.
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