Alternate Method for the Dimerization of 2-Benzylidene inden-1-one Derivatives: Synthesis of 1,3-Diaryl-1,3,3a,8a-tetrahydro-8Hspiro[cyclopenta[a]indene-2,2'-indene]-1',8(3'H)-diones
Öz
In the present study, a series of 1,3-diaryl-1,3,3a,8a-tetrahydro-8H-spiro[cyclopenta[a]indene-2,2'-indene]-1',8(3'H)-dione
derivatives (4a-h)
were synthesized by KOt-Bu catalyzed dimerization of 2-benzylidene
inden-1-one derivatives. The structures of obtained novel spiro-dimeric
compounds were characterized using the spectroscopic methods (1H, 13C, 2D NMR and IR).
Anahtar Kelimeler
2-Benzylidene inden-1-one dimerization spirocyclic-dimer chalcone like compound
Kaynakça
- [1]. P. Singh, A. Anand, V. Kumar, Europ. J. Med. Chem. 2014, 85, 758-777.
- [2]. B. Sharifzadeh, N. O. Mahmoodi, M. Mamaghani, K. Tabatabaeian, A. S. Chirani, I. Nikokar, Bioorg. Med. Chem. Lett. 2013, 23, 548-551.
- [3]. M. S. Nel, A. Petzer, J. P. Petzer, L. J. Legoabe, Bioorg. Chem. 2016, 69, 20-28.
- [4]. S. Rizzo, M. Bartolini, L. Ceccarini, L. Piazzi, S. Gobbi, A. Cavalli, M. Recanatini, V. Andrisano and A. Rampa, Bioorg. Med. Chem. 2010, 18, 1749-1760.
- [5]. G. A. Tunbridge, J. Oram, L. Caggiano, Med. Chem. Commun. 2013, 4, 1452-1456.
- [6]. Singh, K. Fatima, A. Singh, A. Behl, M. J. Mintoo, M. Hasanain, R. Ashraf, S. Luqman, K. Shanker, D. M. Mondhe, J. Sarkar, D. Chanda, A. S. Negi. Europ. J. Pharm. Sci., 2015, 76, 57-67.
- [7]. H. Aichaoui, F. Guenadil, C. N. Kapanda, D. M. Lambert, C. R. McCurdy, J. H. Poupaert, Med. Chem. Res. 2009, 18, 467-476.
- [8]. Saxena, U. Faridi, S. Srivastava, J. Kumar, M. Darokar, S. Luqman, S. Chanotiya, V. Krishna, S. Negi, S. Khanuja, Bioorg. Med. Chem. Lett. 2008, 18, 3914-3918.
- [9]. S. A. F. Rostom, I. M. El-Ashmawy, H. A. Abd El Razik, M. H. Badr, H. M. A. Ashour, Bioorg. Med. Chem. 2009, 17, 882-895.
- [10]. K. V. Diveshkumar, S. Sakrikar, S. Harikrishna, V. Dhamodharan, P. I. Pradeepkumar, Chem. Med. Chem. 2014, 9, 2754-2765.
- [11]. T. M. Kadayat, C. Park, K.-Y. Jun, T. B. T. Magar, G. Bist, H. Y. Yoo, Y. Kwon, E.-S. Lee, Europ. J. Med. Chem. 2015, 90, 302-314.
- [12]. Ş. Öztürk, M. B. Gürdere, H. Gezegen, M. Ceylan, Y. Budak, Org. Commun. 2016, 9,125-132.
- [13]. G. Narang, D. P. Jindal, B. Jit, R. Bansal, Helv. Chim. Acta 2006, 89, 258-264.
- [14]. C. Berthelette, C. McCooye, Y. Leblanc, L. A. Trimble, J. Org. Chem. 1997, 62, 4339-4342.
- [15]. Y. Leblanc, C. Dufresne, R. Dhawan, J. Ollerenshaw, A. Littke, L. A. Trimble, N. N. Tsou, Can. J. Chem. 2000, 78, 784-790.
- [16]. W. Wendelin, K. Schermanz, E. Breitmaier, Monatsh. Chem. 1988, 119, 355-365.
- [17]. W. J. Houlihan, M. J. Shapiro, J. A. Chin, J. Org. Chem. 1997, 62, 1529-1531.
- [18]. P. Camps, L. R. Domingo, X. Formosa, C. Galdeano, D. Gonzalez, D. Munoz-Torrero, S. Segales, M. Font-Bardia, X. Solans, J. Org. Chem. 2006, 71, 3464-3471.
- [19]. İ. Karaman, H. Gezegen, M. B. Gürdere, A. Dingil, M. Ceylan, Chem. Biodiv. 2010, 7, 400-408.
2-Benziliden inden-1-on Türevlerinin Dimerleşmesi için Alternatif Yöntem: 1,3-Diaril-l,3,3a,8a-tetrahidro-8H-spiro[siklopenta[a]inden-2,2'-inden]-1',8(3'H)-dionların Sentezi
Öz
Bu çalışmada, bir seri 1,3-Diaril-l,3,3a,8a-tetrahidro-8H-spiro[siklopenta[a]inden-2,2'-inden]-1',8(3'H)-dion
türevi (4a-h),
2-benziliden inden-1-on türevlerinin KOt-Bu katalizli dimerleşmesi yolu
ile sentezlendi. Elde edilen yeni spiro-dimerik bileşiklerin yapıları
spektroskopik yöntemlerle (1H, 13C, 2D NMR ve IR)
karakterize edildi.
Anahtar Kelimeler
2-Benziliden inden-1-on dimerleşme spirohalkalı-dimer kalkon tipi bileşik
Kaynakça
- [1]. P. Singh, A. Anand, V. Kumar, Europ. J. Med. Chem. 2014, 85, 758-777.
- [2]. B. Sharifzadeh, N. O. Mahmoodi, M. Mamaghani, K. Tabatabaeian, A. S. Chirani, I. Nikokar, Bioorg. Med. Chem. Lett. 2013, 23, 548-551.
- [3]. M. S. Nel, A. Petzer, J. P. Petzer, L. J. Legoabe, Bioorg. Chem. 2016, 69, 20-28.
- [4]. S. Rizzo, M. Bartolini, L. Ceccarini, L. Piazzi, S. Gobbi, A. Cavalli, M. Recanatini, V. Andrisano and A. Rampa, Bioorg. Med. Chem. 2010, 18, 1749-1760.
- [5]. G. A. Tunbridge, J. Oram, L. Caggiano, Med. Chem. Commun. 2013, 4, 1452-1456.
- [6]. Singh, K. Fatima, A. Singh, A. Behl, M. J. Mintoo, M. Hasanain, R. Ashraf, S. Luqman, K. Shanker, D. M. Mondhe, J. Sarkar, D. Chanda, A. S. Negi. Europ. J. Pharm. Sci., 2015, 76, 57-67.
- [7]. H. Aichaoui, F. Guenadil, C. N. Kapanda, D. M. Lambert, C. R. McCurdy, J. H. Poupaert, Med. Chem. Res. 2009, 18, 467-476.
- [8]. Saxena, U. Faridi, S. Srivastava, J. Kumar, M. Darokar, S. Luqman, S. Chanotiya, V. Krishna, S. Negi, S. Khanuja, Bioorg. Med. Chem. Lett. 2008, 18, 3914-3918.
- [9]. S. A. F. Rostom, I. M. El-Ashmawy, H. A. Abd El Razik, M. H. Badr, H. M. A. Ashour, Bioorg. Med. Chem. 2009, 17, 882-895.
- [10]. K. V. Diveshkumar, S. Sakrikar, S. Harikrishna, V. Dhamodharan, P. I. Pradeepkumar, Chem. Med. Chem. 2014, 9, 2754-2765.
- [11]. T. M. Kadayat, C. Park, K.-Y. Jun, T. B. T. Magar, G. Bist, H. Y. Yoo, Y. Kwon, E.-S. Lee, Europ. J. Med. Chem. 2015, 90, 302-314.
- [12]. Ş. Öztürk, M. B. Gürdere, H. Gezegen, M. Ceylan, Y. Budak, Org. Commun. 2016, 9,125-132.
- [13]. G. Narang, D. P. Jindal, B. Jit, R. Bansal, Helv. Chim. Acta 2006, 89, 258-264.
- [14]. C. Berthelette, C. McCooye, Y. Leblanc, L. A. Trimble, J. Org. Chem. 1997, 62, 4339-4342.
- [15]. Y. Leblanc, C. Dufresne, R. Dhawan, J. Ollerenshaw, A. Littke, L. A. Trimble, N. N. Tsou, Can. J. Chem. 2000, 78, 784-790.
- [16]. W. Wendelin, K. Schermanz, E. Breitmaier, Monatsh. Chem. 1988, 119, 355-365.
- [17]. W. J. Houlihan, M. J. Shapiro, J. A. Chin, J. Org. Chem. 1997, 62, 1529-1531.
- [18]. P. Camps, L. R. Domingo, X. Formosa, C. Galdeano, D. Gonzalez, D. Munoz-Torrero, S. Segales, M. Font-Bardia, X. Solans, J. Org. Chem. 2006, 71, 3464-3471.
- [19]. İ. Karaman, H. Gezegen, M. B. Gürdere, A. Dingil, M. Ceylan, Chem. Biodiv. 2010, 7, 400-408.
Ayrıntılar
| Birincil Dil | İngilizce |
|---|---|
| Bölüm | Makaleler |
| Yazarlar | |
| Yayımlanma Tarihi | 30 Eylül 2017 |
| Gönderilme Tarihi | 28 Temmuz 2017 |
| Kabul Tarihi | 21 Eylül 2017 |
| Yayımlandığı Sayı | Yıl 2017 |