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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

Year 2017, , 594 - 601, 30.09.2017

Hayreddin Gezegen

https://doi.org/10.17776/csj.340522
Cited By: 1

Abstract

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).

Keywords

2-Benzylidene inden-1-one dimerization spirocyclic-dimer chalcone like compound

References

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  • [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.
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  • [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.
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  • [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

Year 2017, , 594 - 601, 30.09.2017

Hayreddin Gezegen

https://doi.org/10.17776/csj.340522
Cited By: 1

Abstract

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.

Keywords

2-Benziliden inden-1-on dimerleşme spirohalkalı-dimer kalkon tipi bileşik

References

  • [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.
There are 19 citations in total.

Details

Primary Language English
Journal Section Articles
Authors

Hayreddin Gezegen

Publication Date September 30, 2017
Submission Date July 28, 2017
Acceptance Date September 21, 2017
Published in Issue Year 2017

Cite

APA Gezegen, H. (2017). 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. Cumhuriyet Science Journal, 38(3), 594-601. https://doi.org/10.17776/csj.340522

Cited By

Michael/Michael Addition Cascade of 2‐Benzylidene‐1‐indanones with Chalcones: Synthesis and Biological Evaluations of Novel Polycyclic Compounds
ChemistrySelect
Hayreddin Gezegen
https://doi.org/10.1002/slct.202102738