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Stereospecific Synthesis of cis/trans-dicarbamates

Year 2024, Volume: 14 Issue: 1, 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

cis/trans-dikarbamatların Stereospesifik Sentezi

Year 2024, Volume: 14 Issue: 1, 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
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 Volume: 14 Issue: 1

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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