Synthesis, characterization and X-ray crystallography study of stable ylide of di-tert-butyl-2-(2-indolinon-1-yl)-3-(trimethoxyphosphorane ylidene) butanedioate

Sajadikhah, Seyed Sajad; Mansouri, Ghobad; Rostami-Charati, Faramarz; Makha, Mohamed; Ghobadi, Massoud

doi:10.22075/chem.2022.24342.2008

Synthesis, characterization and X-ray crystallography study of stable ylide of di-tert-butyl-2-(2-indolinon-1-yl)-3-(trimethoxyphosphorane ylidene) butanedioate

Document Type : Original Article

Authors

¹ Department of Chemistry, Payame Noor University, P.O. Box 19395-4697 Tehran, Iran

² Research Center for Conservation of Culture Relicst (RCCCR), Research Institute of Cultural Heritage & Tourism, Tehran, Iran

³ School of Biomedical, Biomolecular and Chemical Sciences, M310, University of Western Australia, Perth, WA 6009, Australia

⁴ Ilam Petrochemical, Company (ILPC), P.O. BOX 6931994749 ,Ilam, Iran

10.22075/chem.2022.24342.2008

Abstract

Stable ylide of di-tert-butyl-2-(2-indolinon-1-yl)-3-(trimethoxyphosphorane ylidene) butanedioate was synthesized by means of catalyst-free reaction of trimethyl phosphite, di-tert-butylacetylene dicarboxylate and 2-indolinone in n-hexane/diethyl ether at ambient temperature. Obtained product was characterized by 1H, 13C, 31P NMR, FT-IR and mass spectroscopy. The crystal structure of the stable ylide was determined by X-ray crystallography. The title compound crystallized in monoclinic, space group P21/c and cell parameters a=15.8079(7) Å, b= 18.7521(13) Å, c =17.4987(10) Å, β= 95.504(6)° and Z=8. The X-ray study showed that adjacent carbonyl group (C291=O291, C191=O191) in the ylide moiety of compound had a resonance with bond of C=P. These results show clearly that environment of C(19, 29) is planar.

Keywords

Main Subjects

Organic Chemistry

This is an open access article under the CC-BY-SA 4.0 license.( https://creativecommons.org/licenses/by-sa/4.0/)

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Synthesis, characterization and X-ray crystallography study of stable ylide of di-tert-butyl-2-(2-indolinon-1-yl)-3-(trimethoxyphosphorane ylidene) butanedioate

References

[1] Tang, Z., Kong, N., Ouyang, J., Feng, C., Kim, N. Y., Ji, X., Wang, C., Farokhzad, O. C., Zhang, H., & Tao, W. (2020). Phosphorus Science-Oriented Design and Synthesis of Multifunctional Nanomaterials for Biomedical Applications. Matter, 2(2), 297-322.

[2] Fabiańska, I., Bucher, M., & Häusler, R. E. (2019). Intracellular phosphate homeostasis – A short way from metabolism to signaling. Plant Sci, 286, 57-67.

[3] Puziy, A. M., Poddubnaya, O. I., Gawdzik, B., & Tascón, J. M. D. (2020). Phosphorus-containing carbons: Preparation, properties and utilization. Carbon, 157. 796-846.

[4] Bozorgvar, M. S., Tarahhomi, A., & Van der Lee, A. (1400). Synthesis and structural study of two new phosphorus-oxygen compounds belonging to two different families of phosphoriamides and phosphates. Applied Chemistry, 16(58), 95-106. ( in Persian)

[5] Tarahhomi, A., Pourayoubi, M. J., Golen, A., & Rheingold, A. L. (1396). Synthesis, characterization and structural study of new phosphoric triamides. Applied Chemistry,12(42), 243-252. (in Persian)

[6] Tarahhomi, A., Rheingold,A. L., & Golen, J. A. (2017) . Synthesis, crystal structure and Hirshfeld surface analysis of new phosphoric triamide [2-F-C₆H₄C(O)NH]P(O)[NHCH(CH₃)₂]₂. Applied Chemistry,11 (41) , 23-30. (in Persian)

[7] Kolodiazhnyi, O. I., Kukhar, V. P & Kolodiazhna, A. O. (2014). Asymmetric catalysis as a method for the synthesis of chiral organophosphorus compounds. Tetrahedron: Asymmetry, 25 (12), 865-922.

[8] Kawaguchi, S-I., Yamamoto,Y., & Ogawa, A. (2020). Catalytic synthesis of sulfur and phosphorus compounds via atom-economic reactions. Mendeleev Commun.30(2), 129-138.

[9] Ramazani, A., & Kazemizadeh, A. R. (2011). Preparation of Stabilized Phosphorus Ylides via Multicomponent Reactions and Their Synthetic Application. Curr., Org. Chem. 15, 3986-4020.

[12] Maghsoodlou, M., Heydari,T. R., Hazeri, N., Habibi-Khorassani, S. M., Barahuie, F., Navidno, J., Rostamizadeh, M., & Sajadikhah, S. S. (2015). An efficient one-pot synthesis of C-alkylated phenols and benzofuran derivatives with phosphanylidene substituents. Res. Chem. Intermed. 41, 2609-2617.

[13] Ramazani, A., Kazemizadeh, A. R., Ahmadi, E., Noshiranzadeh, N., & Souldozi, A. (2008). Synthesis and Reactions of Stabilized Phosphorus Ylides. Curr. Org. Chem. 12 (1), 59-82.

[15] Wittig, G., & Rieber, M. (1949). Über die Metallierbarkeit von quaternären Ammonium‐ und Phosphonium‐Salzen. Justus Liebigs Ann. Chem.562(3), 177-186.

[16] Wittig, G., & Geissler, G. (1953). Zur Reaktionsweise des Pentaphenyl‐phosphors und einiger Derivate. Justus Liebigs Ann. Chem. 580(1), 44-57.

[19] Ismail, T., Shafi, S., Srinivas, J., Sarkar, D., Qurishi, Y., Khazir, J., Alam, M. S., & Kumar, H. M. S. (2016). Synthesis and tyrosinase inhibition activity of trans-stilbene derivatives. Bioorg. Chem.64, 97-102.

[20] Pugachev, M. V., Bulatov, T. M., Nguyen, T. T. N., Pavelyev, R. S., Gnezdilov, O. I., Lodochnikova, O. A., Islamov, D. R., Kataeva, O. N., Balakin, K. V., & Shtyrlin,Y. G. (2017). Wittig reactions of a bis-triphenylphosphonium pyridoxine derivative. Tetrahedron Lett.58 (8), 766-769.

[21] Diaz-Muñoz, G., Isidorio, R. G., Miranda, I. L., de S. Dias, G. N., Diaz., & M. A. N. (2017). A concise and efficient synthesis of tetrahydroquinoline alkaloids using the phase transfer mediated Wittig olefination reaction. Tetrahedron Lett. 58(23), 3311-3315.

[22] Tsai, Y-L., Syu, S -E., Yang, S -M., Das, U., Fan, Y -S., Lee, C-J & Lin, W. (2014). Synthesis of multi-functional alkenes via Wittig reaction with a new-type of phosphorus ylides.Tetrahedron. 70(34), 5038-5045.

[23] Üngören, Ş. H., Albayrak, S., Günay, A., Yurtseven, L., & N. Yurttaş. (2015). A new method for the preparation of 5-acylidene and 5-imino substituted rhodanine derivatives and their antioxidant and antimicrobial activities. Tetrahedron. 71(24) 4312-4323.

[30] Castañeda, F., Silva, P., Bunton, C .A., Garland, M. T., & Baggio, R. (2011). Conformations of diester triphenylphosphonium ylides with an ylidic ester or keto and ester ylidic groups. Acta Cryst, C 67, o319-o323.

[32] Prabha, E. A. J. Y., Kumar, S. S, Padala, A. K., Ahmed, Q. N., & Athimoolam, S. (2016). Crystal structure of ethyl 2-[2-(4-methyl-benzo-yl)-5-p-tolyl-1H-imidazol-1-yl]acetate. Acta Cryst. E 72 (3), 347-349.

Volume 18, Issue 66
April 2023
Pages 147-158

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Synthesis, characterization and X-ray crystallography study of stable ylide of di-tert-butyl-2-(2-indolinon-1-yl)-3-(trimethoxyphosphorane ylidene) butanedioate

References

[1] Tang, Z., Kong, N., Ouyang, J., Feng, C., Kim, N. Y., Ji, X., Wang, C., Farokhzad, O. C., Zhang, H., & Tao, W. (2020). Phosphorus Science-Oriented Design and Synthesis of Multifunctional Nanomaterials for Biomedical Applications. Matter, 2(2), 297-322.

[2] Fabiańska, I., Bucher, M., & Häusler, R. E. (2019). Intracellular phosphate homeostasis – A short way from metabolism to signaling. Plant Sci, 286, 57-67.

[3] Puziy, A. M., Poddubnaya, O. I., Gawdzik, B., & Tascón, J. M. D. (2020). Phosphorus-containing carbons: Preparation, properties and utilization. Carbon, 157. 796-846.

[4] Bozorgvar, M. S., Tarahhomi, A., & Van der Lee, A. (1400). Synthesis and structural study of two new phosphorus-oxygen compounds belonging to two different families of phosphoriamides and phosphates. Applied Chemistry, 16(58), 95-106. ( in Persian)

[5] Tarahhomi, A., Pourayoubi, M. J., Golen, A., & Rheingold, A. L. (1396). Synthesis, characterization and structural study of new phosphoric triamides. Applied Chemistry,12(42), 243-252. (in Persian)

[6] Tarahhomi, A., Rheingold,A. L., & Golen, J. A. (2017) . Synthesis, crystal structure and Hirshfeld surface analysis of new phosphoric triamide [2-F-C6H4C(O)NH]P(O)[NHCH(CH3)2]2. Applied Chemistry,11 (41) , 23-30. (in Persian)

[7] Kolodiazhnyi, O. I., Kukhar, V. P & Kolodiazhna, A. O. (2014). Asymmetric catalysis as a method for the synthesis of chiral organophosphorus compounds. Tetrahedron: Asymmetry, 25 (12), 865-922.

[8] Kawaguchi, S-I., Yamamoto,Y., & Ogawa, A. (2020). Catalytic synthesis of sulfur and phosphorus compounds via atom-economic reactions. Mendeleev Commun.30(2), 129-138.

[9] Ramazani, A., & Kazemizadeh, A. R. (2011). Preparation of Stabilized Phosphorus Ylides via Multicomponent Reactions and Their Synthetic Application. Curr., Org. Chem. 15, 3986-4020.

[12] Maghsoodlou, M., Heydari,T. R., Hazeri, N., Habibi-Khorassani, S. M., Barahuie, F., Navidno, J., Rostamizadeh, M., & Sajadikhah, S. S. (2015). An efficient one-pot synthesis of C-alkylated phenols and benzofuran derivatives with phosphanylidene substituents. Res. Chem. Intermed. 41, 2609-2617.

[13] Ramazani, A., Kazemizadeh, A. R., Ahmadi, E., Noshiranzadeh, N., & Souldozi, A. (2008). Synthesis and Reactions of Stabilized Phosphorus Ylides. Curr. Org. Chem. 12 (1), 59-82.

[15] Wittig, G., & Rieber, M. (1949). Über die Metallierbarkeit von quaternären Ammonium‐ und Phosphonium‐Salzen. Justus Liebigs Ann. Chem.562(3), 177-186.

[16] Wittig, G., & Geissler, G. (1953). Zur Reaktionsweise des Pentaphenyl‐phosphors und einiger Derivate. Justus Liebigs Ann. Chem. 580(1), 44-57.

[19] Ismail, T., Shafi, S., Srinivas, J., Sarkar, D., Qurishi, Y., Khazir, J., Alam, M. S., & Kumar, H. M. S. (2016). Synthesis and tyrosinase inhibition activity of trans-stilbene derivatives. Bioorg. Chem.64, 97-102.

[20] Pugachev, M. V., Bulatov, T. M., Nguyen, T. T. N., Pavelyev, R. S., Gnezdilov, O. I., Lodochnikova, O. A., Islamov, D. R., Kataeva, O. N., Balakin, K. V., & Shtyrlin,Y. G. (2017). Wittig reactions of a bis-triphenylphosphonium pyridoxine derivative. Tetrahedron Lett.58 (8), 766-769.

[21] Diaz-Muñoz, G., Isidorio, R. G., Miranda, I. L., de S. Dias, G. N., Diaz., & M. A. N. (2017). A concise and efficient synthesis of tetrahydroquinoline alkaloids using the phase transfer mediated Wittig olefination reaction. Tetrahedron Lett. 58(23), 3311-3315.

[22] Tsai, Y-L., Syu, S -E., Yang, S -M., Das, U., Fan, Y -S., Lee, C-J & Lin, W. (2014). Synthesis of multi-functional alkenes via Wittig reaction with a new-type of phosphorus ylides.Tetrahedron. 70(34), 5038-5045.

[23] Üngören, Ş. H., Albayrak, S., Günay, A., Yurtseven, L., & N. Yurttaş. (2015). A new method for the preparation of 5-acylidene and 5-imino substituted rhodanine derivatives and their antioxidant and antimicrobial activities. Tetrahedron. 71(24) 4312-4323.

[30] Castañeda, F., Silva, P., Bunton, C .A., Garland, M. T., & Baggio, R. (2011). Conformations of diester triphenylphosphonium ylides with an ylidic ester or keto and ester ylidic groups. Acta Cryst, C 67, o319-o323.

[32] Prabha, E. A. J. Y., Kumar, S. S, Padala, A. K., Ahmed, Q. N., & Athimoolam, S. (2016). Crystal structure of ethyl 2-[2-(4-methyl-benzo-yl)-5-p-tolyl-1H-imidazol-1-yl]acetate. Acta Cryst. E 72 (3), 347-349.

Volume 18, Issue 66April 2023Pages 147-158

Files

Share

How to cite

Statistics

[6] Tarahhomi, A., Rheingold,A. L., & Golen, J. A. (2017) . Synthesis, crystal structure and Hirshfeld surface analysis of new phosphoric triamide [2-F-C₆H₄C(O)NH]P(O)[NHCH(CH₃)₂]₂. Applied Chemistry,11 (41) , 23-30. (in Persian)

Volume 18, Issue 66
April 2023
Pages 147-158