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cis/trans-dikarbamatların Stereospesifik Sentezi

Year 2024, , 94 - 105, 30.06.2024

Latif Kelebekli

https://doi.org/10.54370/ordubtd.1360498

Abstract

Yeni bir allilik cis/trans-dikarbamat sınıfının verimli sentezi açıklanmaktadır. Hedeflenen bileşiklerin anahtar ara maddeleri olarak allilik dioller, p-benzokinon'dan başlayarak kolay bir şekilde hazırlandı. Allilik diol bileşiklerinin p-TsNCO ile reaksiyonu cis/trans-dikarbamat gruplarının oluşumuyla sonuçlandı. cis/trans-Dikarbamatların yapısı 1H-NMR, 13C-NMR, FT-IR ve elemental analiz teknikleriyle aydınlatıldı.

Keywords

stereospesifik bis-karbamatlar trans-karbamat cis-karbamat

References

  • Chander, S., Ashok, P., Zheng, Y. T., Wang, P., Raja, K. S., Taneja, A., & Murugesan, S. (2016). Design, synthesis and in-vitro evaluation of novel tetrahydroquinoline carbamates as HIV-1 RT inhibitor and their antifungal activity. Bioorganic Chemistry, 64, 66–73. https://doi.org/10.1016/j.bioorg.2015.12.005
  • Dal Corso, A., Borlandelli, V., Corno, C., Perego, P., Belvisi, L., Pignataro, L., & Gennari, C. (2020). Fast cyclization of a proline-derived self-immolative spacer improves the efficacy of carbamate prodrugs. Angewandte Chemie International Edition, 59, 4176–4181. https://doi.org/10.1002/anie.201916394
  • Franz, M., Stalling, T., Steinert H., & Martens, J. (2018). First catalyst-free CO2 trapping of N-acyliminium ions under ambient conditions: sustainable multicomponent synthesis of thia-and oxazolidinyl carbamates. Organic Biomolecular Chemistry, 16, 6914-6926. https://doi.org/10.1039/C8OB01865K Ghosh, A. K., & Brindisi, M. (2015). Organic carbamates in drug design and medicinal chemistry. Journal of Medicinal Chemistry, 58, 2895−2940. https://doi.org/10.1021/jm501371s
  • Ghrairi, S., Retailleau, P., Crousse, B., & Slimi, T. B. (2022). A one-pot synthesis and X-Ray structural characterization of new highly substituted-allyl carbamates. Journal of Molecular Structure, 1258, 132548. https://doi.org/10.1016/j.molstruc.2022.132548
  • Gupte, S. P., Shivarkar, A. B., & Chaudhari, R. V. (2001). Carbamate synthesis by solid-base catalyzed reaction of disubstituted ureas and carbonates. Chemical Communications, 2620−2621. https://doi.org/10.1039/B107947F
  • Huang, D., & Yan, G. (2017). Recent advances in reactions of aryl sulfonyl isocyanates. Organic Biomolecular Chemistry, 15, 1753–1761. https://doi.org/10.1039/C6OB02720B
  • Huxley, C., Wibowo, M., Lum, K. Y., Gordon, S., D’Hyon, S., Guan, H., Wang, X., Chen, Y., Si, M., Wang, M., White, J. M., Wahi, K., Wang, Q., Holst, J., & Davis, R. A. (2020). Synthesis of bilocularin A carbamate derivatives and their evaluation as leucine transport inhibitors in prostate cancer cells. Phytochemistry, 179, 112478. https://doi.org/10.1016/j.phytochem.2020.112478
  • Ishii, Y., Ito, S., Saito, Y., Uno, D., & Oba, T. (2015). Synthesis of [2,3]Naphthoporphyrins Using 4,9-Dihydro-4,9-Ethano-2H-Benz[f]Isoindole as a Benz[f]Isoindole Equivalent. Tetrahedron, 71, 8892–8898. https://doi.org/10.1016/j.tet.2015.09.072
  • Kelebekli, L., Balcı, N., & Şahin, E. (2012). Oxazolidinone polycyclitols. Stereospecific synthesis of novel aminocarbasugars with oxazolidinone ring. Tetrahedron, 68, 1886–1893. https://doi.org/10.1016/j.tet.2011.12.078
  • Kelebekli, L. (2013). Stereoselective Synthesis of Tricyclo[6.2.2.02,7]Dodecane-3,6,9,10- Tetrol via Selective Reduction of α,β-Unsaturated 1,4-DIKetone. Synthetic Communications, 43, 2998–3009. https://doi.org/10.1080/00397911.2012.754472
  • Kelebekli, L. (2022). Synthesis and hydrolysis of monocarbamate from allylic 1,4-dicarbamate: Bis-homodichloroinositol. Carbohydrate Research, 522, 108681. https://doi.org/10.1016/j.carres.2022.108681
  • Kelebekli, L. (2020). Synthesis of N-acetyl-4-methyl-benzenesulfonamide from Chloramine-T. Ordu Üniversitesi Bilim ve Teknoloji Dergisi, 10(2), 117-124. https://dergipark.org.tr/en/pub/ordubtd/issue/58759/823390
  • Kelebekli, L., & Atlı, I. (2019). Stereoselective synthesis of a new methyl-substituted inositol Derivative. Tetrahedron, 75, 130531. https://doi.org/10.1016/j.tet.2019.130531
  • Kelebekli, L., & Şahin, E. (2023). Stereospecific synthesis of Pd(0)-catalyzed oxazolidinone with tetracyclic structure. Synthetic Communications, 53, 1832-1843. https://doi.org/10.1080/00397911.2023.2252537
  • Košak, U., Strašek, N., Knez, D., Jukiˇc, M., Žakelj, S., Zahirovi´c, A., & Gobec, S. (2020). N-alkylpiperidine carbamates as potential anti-Alzheimer’s agents. European Journal of Medicinal Chemistry, 197, 112282. https://doi.org/10.1016/j.ejmech.2021.113282
  • Krzywik, J., Aminpour, M., Janczak, J., Maj, E., Moshari, M., Mozga, W., Wietrzyk, J., Tuszy´nski, J. A., & Huczy´nski, A. (2021). An insight into the anticancer potential of carbamates and thiocarbamates of 10-demethoxy-10-methylaminocolchicine. European Journal of Medicinal Chemistry, 215, 113282. https://doi.org/10.1016/j.ejmech.2021.113282
  • Li, X., Zhan, P., De Clercq, E., & Liu, X. (2012). The HIV-1 non-nucleoside reverse transcriptase inhibitors (Part V): Capravirine and its analogues. Current Medicinal Chemistry, 19, 6138–6149. https://doi.org/10.2174/092986712804485764
  • Löscher, W., Sills, G. J., & White, H. S. (2021). The ups and downs of alkyl-carbamates in epilepsy therapy: how does cenobamate differ? Epilepsia, 62, 596–614. https://doi.org/10.1111/epi.16832
  • Luche, J. L. (1978). Lanthanides in Organic Chemistry. 1. Selective 1,2 Reductions of Conjugated Ketones. Journal of the American Chemical Society, 100, 2226–2227. https://doi.org/10.1021/ja00475a040
  • Marchand, A. P., LaRoe, W. D., Sharma, G. V. M., Suri, S. C., Reddy, D. S. (1986). Facile Stereoselective Reductions of Enediones and Cage Diketones Suing Sodium Borohydride-Cerium(III) Chloride. The Journal of Organic Chemistry, 51, 1622–1625. https://doi.org/10.1021/jo00359a054
  • Matošević, A., & Bosak, A. (2020). Carbamate group as structural motif in drugs: a review of carbamate derivatives used as therapeutic agents. Archives of Industrial Hygiene and Toxicology, 71, 285–299. https://doi.org/10.2478/aiht-2020-71-3466
  • Mattarei, A., Azzolini, M., Zoratti, M., Biasutto, L., & Paradisi, C. (2015). N- Monosubstituted Methoxy-oligo(ethylene glycol) carbamate ester pro- drugs of resveratrol. Molecules, 20, 16085–16102. https://doi.org/10.3390/molecules200916085
  • Mizutani, T., Ishikawa, S., Nagase, T., Takahashi, H., Fujimura, T., Sasaki, T., Nagumo, A., Shimamura, K., Miyamoto, Y., Kitazawa, H., Kanesaka, M., Yoshimoto, R., Aragane, K., Tokita, S., & Sato, N. (2009). Discovery of novel benzoxazinones as potent and orally active long chain fatty acid elongase 6 inhibitors. Journal of Medicinal Chemistry, 52, 7289–7300. https://doi.org/10.1021/jm900915x
  • Prasher, P., Mall, T., & Sharma, M. (2023). Cyclic carbamates in medicine: A clinical perspective. Drug Development Research, 84, 397–405. https://doi.org/10.1002/ddr.22033
  • Seo, U. R., & Chung, Y. K. (2017). Potassium Phosphate-Catalyzed One-pot Synthesis of 3-Aryl-2-oxazolidinones from Epoxides, Amines, and an Atmospheric Carbon Dioxide. Green Chemistry, 19, 803–808. https://doi.org/10.1039/C6GC02934E
  • Scattolin, T., Bouayad-Gervais, S., & Schoenebeck, F. (2019). Straightforward access to N-trifluoromethyl amides, carbamates, thiocarbamates and ureas. Nature, 573, 102–107. https://doi.org/10.1038/s41586-019-1518-3
  • Trost, B. T., & Kalnmals, C. A. (2020). Annulative Allylic Alkylation Reactions between Dual Electrophiles and Dual Nucleophiles: Applications in Complex Molecule Synthesis. Chemistry A European Journal, 26, 1906 – 1921. https://doi.org/10.1002/chem.201903961
  • Vacondio, F., Silva, C., Mor, M., & Testa, B. (2010). Qualitative structure-metabolism relationships in the hydrolysis of carbamates. Drug Metabolism Reviews, 42(4), 551–589. https://doi.org/10.3109/03602531003745960
  • Yakan, H. (2020). Novel Schiff bases derived from isothiocyanates: synthesis, characterization, and antioxidant activity. Research on Chemical Intermediates, 46, 3979–3995. https://doi.org/10.1007/s11164-020-04185-w

Stereospecific Synthesis of cis/trans-dicarbamates

Year 2024, , 94 - 105, 30.06.2024

Latif Kelebekli

https://doi.org/10.54370/ordubtd.1360498

Abstract

The efficient synthesis of a new class of allylic cis/trans-dicarbamates are described. Allylic diols as key intermediates of the targeted compounds were prepared in a facile way, starting from p-benzoquinone. Reaction of allylic diol compounds with p-TsNCO resulted in the formation of cis/trans-dicarbamate groups. The structure of cis/trans-dicarbamates were determined by 1H-NMR, 13C-NMR, FT-IR and elemental analysis techniques.

Keywords

Stereospecific bis-carbamates trans-carbamate cis-carbamate

References

  • Chander, S., Ashok, P., Zheng, Y. T., Wang, P., Raja, K. S., Taneja, A., & Murugesan, S. (2016). Design, synthesis and in-vitro evaluation of novel tetrahydroquinoline carbamates as HIV-1 RT inhibitor and their antifungal activity. Bioorganic Chemistry, 64, 66–73. https://doi.org/10.1016/j.bioorg.2015.12.005
  • Dal Corso, A., Borlandelli, V., Corno, C., Perego, P., Belvisi, L., Pignataro, L., & Gennari, C. (2020). Fast cyclization of a proline-derived self-immolative spacer improves the efficacy of carbamate prodrugs. Angewandte Chemie International Edition, 59, 4176–4181. https://doi.org/10.1002/anie.201916394
  • Franz, M., Stalling, T., Steinert H., & Martens, J. (2018). First catalyst-free CO2 trapping of N-acyliminium ions under ambient conditions: sustainable multicomponent synthesis of thia-and oxazolidinyl carbamates. Organic Biomolecular Chemistry, 16, 6914-6926. https://doi.org/10.1039/C8OB01865K Ghosh, A. K., & Brindisi, M. (2015). Organic carbamates in drug design and medicinal chemistry. Journal of Medicinal Chemistry, 58, 2895−2940. https://doi.org/10.1021/jm501371s
  • Ghrairi, S., Retailleau, P., Crousse, B., & Slimi, T. B. (2022). A one-pot synthesis and X-Ray structural characterization of new highly substituted-allyl carbamates. Journal of Molecular Structure, 1258, 132548. https://doi.org/10.1016/j.molstruc.2022.132548
  • Gupte, S. P., Shivarkar, A. B., & Chaudhari, R. V. (2001). Carbamate synthesis by solid-base catalyzed reaction of disubstituted ureas and carbonates. Chemical Communications, 2620−2621. https://doi.org/10.1039/B107947F
  • Huang, D., & Yan, G. (2017). Recent advances in reactions of aryl sulfonyl isocyanates. Organic Biomolecular Chemistry, 15, 1753–1761. https://doi.org/10.1039/C6OB02720B
  • Huxley, C., Wibowo, M., Lum, K. Y., Gordon, S., D’Hyon, S., Guan, H., Wang, X., Chen, Y., Si, M., Wang, M., White, J. M., Wahi, K., Wang, Q., Holst, J., & Davis, R. A. (2020). Synthesis of bilocularin A carbamate derivatives and their evaluation as leucine transport inhibitors in prostate cancer cells. Phytochemistry, 179, 112478. https://doi.org/10.1016/j.phytochem.2020.112478
  • Ishii, Y., Ito, S., Saito, Y., Uno, D., & Oba, T. (2015). Synthesis of [2,3]Naphthoporphyrins Using 4,9-Dihydro-4,9-Ethano-2H-Benz[f]Isoindole as a Benz[f]Isoindole Equivalent. Tetrahedron, 71, 8892–8898. https://doi.org/10.1016/j.tet.2015.09.072
  • Kelebekli, L., Balcı, N., & Şahin, E. (2012). Oxazolidinone polycyclitols. Stereospecific synthesis of novel aminocarbasugars with oxazolidinone ring. Tetrahedron, 68, 1886–1893. https://doi.org/10.1016/j.tet.2011.12.078
  • Kelebekli, L. (2013). Stereoselective Synthesis of Tricyclo[6.2.2.02,7]Dodecane-3,6,9,10- Tetrol via Selective Reduction of α,β-Unsaturated 1,4-DIKetone. Synthetic Communications, 43, 2998–3009. https://doi.org/10.1080/00397911.2012.754472
  • Kelebekli, L. (2022). Synthesis and hydrolysis of monocarbamate from allylic 1,4-dicarbamate: Bis-homodichloroinositol. Carbohydrate Research, 522, 108681. https://doi.org/10.1016/j.carres.2022.108681
  • Kelebekli, L. (2020). Synthesis of N-acetyl-4-methyl-benzenesulfonamide from Chloramine-T. Ordu Üniversitesi Bilim ve Teknoloji Dergisi, 10(2), 117-124. https://dergipark.org.tr/en/pub/ordubtd/issue/58759/823390
  • Kelebekli, L., & Atlı, I. (2019). Stereoselective synthesis of a new methyl-substituted inositol Derivative. Tetrahedron, 75, 130531. https://doi.org/10.1016/j.tet.2019.130531
  • Kelebekli, L., & Şahin, E. (2023). Stereospecific synthesis of Pd(0)-catalyzed oxazolidinone with tetracyclic structure. Synthetic Communications, 53, 1832-1843. https://doi.org/10.1080/00397911.2023.2252537
  • Košak, U., Strašek, N., Knez, D., Jukiˇc, M., Žakelj, S., Zahirovi´c, A., & Gobec, S. (2020). N-alkylpiperidine carbamates as potential anti-Alzheimer’s agents. European Journal of Medicinal Chemistry, 197, 112282. https://doi.org/10.1016/j.ejmech.2021.113282
  • Krzywik, J., Aminpour, M., Janczak, J., Maj, E., Moshari, M., Mozga, W., Wietrzyk, J., Tuszy´nski, J. A., & Huczy´nski, A. (2021). An insight into the anticancer potential of carbamates and thiocarbamates of 10-demethoxy-10-methylaminocolchicine. European Journal of Medicinal Chemistry, 215, 113282. https://doi.org/10.1016/j.ejmech.2021.113282
  • Li, X., Zhan, P., De Clercq, E., & Liu, X. (2012). The HIV-1 non-nucleoside reverse transcriptase inhibitors (Part V): Capravirine and its analogues. Current Medicinal Chemistry, 19, 6138–6149. https://doi.org/10.2174/092986712804485764
  • Löscher, W., Sills, G. J., & White, H. S. (2021). The ups and downs of alkyl-carbamates in epilepsy therapy: how does cenobamate differ? Epilepsia, 62, 596–614. https://doi.org/10.1111/epi.16832
  • Luche, J. L. (1978). Lanthanides in Organic Chemistry. 1. Selective 1,2 Reductions of Conjugated Ketones. Journal of the American Chemical Society, 100, 2226–2227. https://doi.org/10.1021/ja00475a040
  • Marchand, A. P., LaRoe, W. D., Sharma, G. V. M., Suri, S. C., Reddy, D. S. (1986). Facile Stereoselective Reductions of Enediones and Cage Diketones Suing Sodium Borohydride-Cerium(III) Chloride. The Journal of Organic Chemistry, 51, 1622–1625. https://doi.org/10.1021/jo00359a054
  • Matošević, A., & Bosak, A. (2020). Carbamate group as structural motif in drugs: a review of carbamate derivatives used as therapeutic agents. Archives of Industrial Hygiene and Toxicology, 71, 285–299. https://doi.org/10.2478/aiht-2020-71-3466
  • Mattarei, A., Azzolini, M., Zoratti, M., Biasutto, L., & Paradisi, C. (2015). N- Monosubstituted Methoxy-oligo(ethylene glycol) carbamate ester pro- drugs of resveratrol. Molecules, 20, 16085–16102. https://doi.org/10.3390/molecules200916085
  • Mizutani, T., Ishikawa, S., Nagase, T., Takahashi, H., Fujimura, T., Sasaki, T., Nagumo, A., Shimamura, K., Miyamoto, Y., Kitazawa, H., Kanesaka, M., Yoshimoto, R., Aragane, K., Tokita, S., & Sato, N. (2009). Discovery of novel benzoxazinones as potent and orally active long chain fatty acid elongase 6 inhibitors. Journal of Medicinal Chemistry, 52, 7289–7300. https://doi.org/10.1021/jm900915x
  • Prasher, P., Mall, T., & Sharma, M. (2023). Cyclic carbamates in medicine: A clinical perspective. Drug Development Research, 84, 397–405. https://doi.org/10.1002/ddr.22033
  • Seo, U. R., & Chung, Y. K. (2017). Potassium Phosphate-Catalyzed One-pot Synthesis of 3-Aryl-2-oxazolidinones from Epoxides, Amines, and an Atmospheric Carbon Dioxide. Green Chemistry, 19, 803–808. https://doi.org/10.1039/C6GC02934E
  • Scattolin, T., Bouayad-Gervais, S., & Schoenebeck, F. (2019). Straightforward access to N-trifluoromethyl amides, carbamates, thiocarbamates and ureas. Nature, 573, 102–107. https://doi.org/10.1038/s41586-019-1518-3
  • Trost, B. T., & Kalnmals, C. A. (2020). Annulative Allylic Alkylation Reactions between Dual Electrophiles and Dual Nucleophiles: Applications in Complex Molecule Synthesis. Chemistry A European Journal, 26, 1906 – 1921. https://doi.org/10.1002/chem.201903961
  • Vacondio, F., Silva, C., Mor, M., & Testa, B. (2010). Qualitative structure-metabolism relationships in the hydrolysis of carbamates. Drug Metabolism Reviews, 42(4), 551–589. https://doi.org/10.3109/03602531003745960
  • Yakan, H. (2020). Novel Schiff bases derived from isothiocyanates: synthesis, characterization, and antioxidant activity. Research on Chemical Intermediates, 46, 3979–3995. https://doi.org/10.1007/s11164-020-04185-w
There are 29 citations in total.

Details

Primary Language English
Subjects Organic Chemical Synthesis
Journal Section Research Articles
Authors

Latif Kelebekli 0000-0002-6242-2589

Early Pub Date June 30, 2024
Publication Date June 30, 2024
Submission Date September 14, 2023
Published in Issue Year 2024

Cite

APA Kelebekli, L. (2024). Stereospecific Synthesis of cis/trans-dicarbamates. Ordu Üniversitesi Bilim Ve Teknoloji Dergisi, 14(1), 94-105. https://doi.org/10.54370/ordubtd.1360498

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