Year 2017, Volume 38, Issue 3, Pages 594 - 601 2017-09-30

Alternate Method for the Dimerization of 2-Benzylidene inden-1-one Derivatives: Synthesis of 1,3-Diaryl-1,3,3a,8a-tetrahydro-8H-spiro[cyclopenta[a]indene-2,2'-indene]-1',8(3'H)-diones
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

Hayreddin GEZEGEN [1]

164 290

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).

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.

  • [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.
Subjects Basic Sciences
Published Date Ekim
Journal Section Articles
Authors

Author: Hayreddin GEZEGEN

Bibtex @research article { csj340522, journal = {Cumhuriyet Science Journal}, issn = {2587-2680}, eissn = {2587-246X}, address = {Cumhuriyet University}, year = {2017}, volume = {38}, pages = {594 - 601}, doi = {10.17776/csj.340522}, title = {Alternate Method for the Dimerization of 2-Benzylidene inden-1-one Derivatives: Synthesis of 1,3-Diaryl-1,3,3a,8a-tetrahydro-8H-spiro[cyclopenta[a]indene-2,2'-indene]-1',8(3'H)-diones}, key = {cite}, author = {GEZEGEN, Hayreddin} }
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-8H-spiro[cyclopenta[a]indene-2,2'-indene]-1',8(3'H)-diones. Cumhuriyet Science Journal, 38 (3), 594-601. DOI: 10.17776/csj.340522
MLA GEZEGEN, H . "Alternate Method for the Dimerization of 2-Benzylidene inden-1-one Derivatives: Synthesis of 1,3-Diaryl-1,3,3a,8a-tetrahydro-8H-spiro[cyclopenta[a]indene-2,2'-indene]-1',8(3'H)-diones". Cumhuriyet Science Journal 38 (2017): 594-601 <http://dergipark.org.tr/csj/issue/31252/340522>
Chicago GEZEGEN, H . "Alternate Method for the Dimerization of 2-Benzylidene inden-1-one Derivatives: Synthesis of 1,3-Diaryl-1,3,3a,8a-tetrahydro-8H-spiro[cyclopenta[a]indene-2,2'-indene]-1',8(3'H)-diones". Cumhuriyet Science Journal 38 (2017): 594-601
RIS TY - JOUR T1 - Alternate Method for the Dimerization of 2-Benzylidene inden-1-one Derivatives: Synthesis of 1,3-Diaryl-1,3,3a,8a-tetrahydro-8H-spiro[cyclopenta[a]indene-2,2'-indene]-1',8(3'H)-diones AU - Hayreddin GEZEGEN Y1 - 2017 PY - 2017 N1 - doi: 10.17776/csj.340522 DO - 10.17776/csj.340522 T2 - Cumhuriyet Science Journal JF - Journal JO - JOR SP - 594 EP - 601 VL - 38 IS - 3 SN - 2587-2680-2587-246X M3 - doi: 10.17776/csj.340522 UR - https://doi.org/10.17776/csj.340522 Y2 - 2017 ER -
EndNote %0 Cumhuriyet Science Journal Alternate Method for the Dimerization of 2-Benzylidene inden-1-one Derivatives: Synthesis of 1,3-Diaryl-1,3,3a,8a-tetrahydro-8H-spiro[cyclopenta[a]indene-2,2'-indene]-1',8(3'H)-diones %A Hayreddin GEZEGEN %T Alternate Method for the Dimerization of 2-Benzylidene inden-1-one Derivatives: Synthesis of 1,3-Diaryl-1,3,3a,8a-tetrahydro-8H-spiro[cyclopenta[a]indene-2,2'-indene]-1',8(3'H)-diones %D 2017 %J Cumhuriyet Science Journal %P 2587-2680-2587-246X %V 38 %N 3 %R doi: 10.17776/csj.340522 %U 10.17776/csj.340522
ISNAD GEZEGEN, Hayreddin . "Alternate Method for the Dimerization of 2-Benzylidene inden-1-one Derivatives: Synthesis of 1,3-Diaryl-1,3,3a,8a-tetrahydro-8H-spiro[cyclopenta[a]indene-2,2'-indene]-1',8(3'H)-diones". Cumhuriyet Science Journal 38 / 3 (September 2017): 594-601. https://doi.org/10.17776/csj.340522