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

Hayreddin Gezegen

doi:10.17776/csj.340522

Araştırma Makalesi

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

Yıl 2017, Cilt: 38 Sayı: 3, 594 - 601, 30.09.2017

Hayreddin Gezegen

https://doi.org/10.17776/csj.340522

Cited By: 1

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

Yıl 2017, Cilt: 38 Sayı: 3, 594 - 601, 30.09.2017

Hayreddin Gezegen

https://doi.org/10.17776/csj.340522

Cited By: 1

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.

Toplam 19 adet kaynakça vardır.

Ayrıntılar

Birincil Dil	İngilizce
Bölüm	Makaleler
Yazarlar	Hayreddin Gezegen
Yayımlanma Tarihi	30 Eylül 2017
Gönderilme Tarihi	28 Temmuz 2017
Kabul Tarihi	21 Eylül 2017
Yayımlandığı Sayı	Yıl 2017Cilt: 38 Sayı: 3

Kaynak Göster

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

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-8Hspiro[cyclopenta[a]indene-2,2'-indene]-1',8(3'H)-diones

Öz

Anahtar Kelimeler

Kaynakça

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

Anahtar Kelimeler

Kaynakça

Ayrıntılar

Kaynak Göster

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