SYNTHESIS OF INDOLES DERIVATIVES USING METAL FREE CATALYST IN ORGANIC REACTIONS
Yıl 2021,
Cilt: 45 Sayı: 3, 615 - 630, 27.09.2021
Ratnesh Das
,
Hemlata Dangi
Sushil Kashaw
Öz
Objective: Indole derivatives are one of the most flexible and common nitrogen-based skeletons and often used in the synthesis of numerous heterocyclic compounds, having biological or medicinal importance. Many indole derivatives have been isolated naturally from plants, fungi, and marine organisms and are highly important due to their pharmaceutical activities. They also play a significant character in polymer and dye industries as well as in the agriculture sector. There exists an immense potential for designing and methodology development for the synthesis of indole based heterocyclic scaffold structure with desire chemical and biomedical relevance.
Result and Discussion: In this present review, we outlined the recent applications of indoles in the one-pot multi-component reaction using metal free catalysts for the preparation of various heterocyclic scaffolds and their corresponding biological activities are also discussed.
Destekleyen Kurum
Dr. Harisingh Gour Central University Sagar MP 470003
Teşekkür
Thankful CSIR, Delhi India for giving me a NET-JRF fellowship grant.
Kaynakça
- 1. Yellappa, S. An anti-Michael route for the synthesis of indole-spiro (indene-pyrrolidine) by 1,3-cycloaddition of azomethineylide with indole-derivatised olefins. J. Heterocycl. Chem. 57, 1083–1089 (2020).
- 2. Tha, S., Shakya, S., Malla, R. & Aryal, P. Prospects of Indole derivatives as methyl transfer inhibitors: Antimicrobial resistance managers. BMC Pharmacol. Toxicol. 21, 1–11 (2020).
- 3. Sayed, M. et al. Design and synthesis of novel indole derivatives with aggregation-induced emission and antimicrobial activity. J. Photochem. Photobiol. A Chem. 383, 111969 (2019).
- 4. Parle, A. & Kumar, N. Synthesis , characterization and evaluation of 3- acetylindole derivatives as potential antifungal agents. 9, 468–474 (2020).
- 5. Mo, Z. Y. et al. Electrochemically enabled functionalization of indoles or anilines for the synthesis of hexafluoroisopropoxy indole and aniline derivatives. Org. Biomol. Chem. 18, 3832–3837 (2020).
- 6. Wei, C., Zhao, L., Sun, Z., Hu, D. & Song, B. Discovery of novel indole derivatives containing dithioacetal as potential antiviral agents for plants. Pestic. Biochem. Physiol. 166, 104568 (2020).
- 7. Turner, D. N., Edwards, L., Kornienko, A., Frolova, L. V. & Rogelj, S. Synergistic action of substituted indole derivatives and clinically used antibiotics against drug-resistant bacteria. Future Microbiol. 15, 579–590 (2020).
- 8. Syahri, J., Hidayah, N., Hilma, R. & Nurohmah, B. A. www.jmolekul.com. (2020).
- 9. Zeng, L., Lin, Y. & Cui, S. Indole-N-Carboxylic Acids and Indole-N-Carboxamides in Organic Synthesis. Chem. - An Asian J. 15, 973–985 (2020).
- 10. Ganguly, N. C., Roy, S., Mondal, P. & Saha, R. An efficient one-pot organocatalytic synthesis of 9-(1H-indol-3-yl)- xanthen-4-(9H)-ones under mild aqueous micellar conditions. Tetrahedron Lett. 53, 7067–7071 (2012).
- 11. Bhattacharjee, S., Das, D. K. & Khan, A. T. Ammonium chloride-catalyzed three-component reaction for the synthesis of fused 4H-chromene derivatives in aqueous medium. Synth. 46, 73–80 (2014).
- 12. Jiang, Y. H. & Yan, C. G. Three-Component Reaction for the Convenient Synthesis of Functionalized 3-{1-[2-(1 H -Indol-3-yl)ethyl]-4,5,6,7-tetrahydro-1 H -indol-3-yl}indolin-2-ones. Synth. 48, 3057–3064 (2016).
- 13. Klenc, J. et al. Synthesis of 4-Substituted 2- ( 4-Methylpiperazino ) pyrimidines and Quinazoline Analogs as Serotonin 5-HT 2A Receptor Ligands. J. Heterocycl. Chem. 46, 1259–1265 (2009).
- 14. Fatma, S. et al. An eco-compatible multicomponent strategy for the synthesis of new 2-amino-6-(1H-indol-3-yl)-4-arylpyridine-3,5-dicarbonitriles in aqueous micellar medium promoted by thiamine-hydrochloride. Tetrahedron Lett. 55, 2201–2207 (2014).
- 15. El-Sayed, N. S. et al. Synthesis of 4-aryl-6-indolylpyridine-3-carbonitriles and evaluation of their antiproliferative activity. Tetrahedron Lett. 55, 1154–1158 (2014).
- 16. Naureen, S. et al. Synthesis of tetrasubstitutd imidazoles containing indole and their antiurease and antioxidant activities. J. Chil. Chem. Soc. 62, 3583–3587 (2017).
- 17. Chen, T., Xu, X. P. & Ji, S. J. Novel, one-pot, three-component route to indol-3-yl substituted spirooxindole derivatives. J. Comb. Chem. 12, 659–663 (2010).
- 18. Chen, X. B., Xiong, S. L., Xie, Z. X., Wang, Y. C. & Liu, W. Three-Component One-Pot Synthesis of Highly Functionalized Bis-Indole Derivatives. ACS Omega 4, 11832–11837 (2019).
- 19. Borpatra, P. J., Deka, B., Rajbongshi, B. K., Deb, M. L. & Baruah, P. K. One-pot sequential multi-component reaction: Synthesis of 3-substituted indoles. Synth. Commun. 48, 2074–2082 (2018).
- 20. Waill A, E., Ghoson M, D., Paul W, T. & Ting-Chi, W. Influence of two extraction methods on essential oils of some Apiaceae family plants. Egypt Pharm. J 18, 160–164 (2019).
- 21. Wang, L. et al. Synthesis of Diastereoenriched Oxazolo[5,4-b]indoles via Catalyst-Free Multicomponent Bicyclizations. J. Org. Chem. 82, 3605–3611 (2017).
- 22. Lin, W., Zheng, Y. X., Xun, Z., Huang, Z. Bin & Shi, D. Q. Microwave-Assisted Regioselective Synthesis of 3-Functionalized Indole Derivatives via Three-Component Domino Reaction. ACS Comb. Sci. 19, 708–713 (2017).
- 23. Zeng, L., Sajiki, H. & Cui, S. Multicomponent Ugi Reaction of Indole- N-carboxylic Acids: Expeditious Access to Indole Carboxamide Amino Amides. Org. Lett. 21, 5269–5272 (2019).
- 24. Singh, V. K., Dubey, R., Upadhyay, A., Sharma, L. K. & Singh, R. K. P. Electrochemical approach for synthesis of 3-substituted indole derivatives. Tetrahedron Lett. 58, 4227–4231 (2017).
- 25. Krishnammagari, S. K., Balwe, S. G., Kim, J. S., Lim, K. T. & Jeong, Y. T. A one-pot four-component domino protocol for the synthesis of indole and coumarin containing pyridine-3-carbonitrile derivatives. Monatshefte fur Chemie 150, 691–702 (2019).
- 26. Mazzotta, S. et al. 3-Amino-alkylated indoles: Unexplored green products acting as anti-inflammatory agents. Future Med. Chem. 12, 5–17 (2019).
- 27. Rathod, A. S., Reddy, P. V. & Biradar, J. S. Microwave-Assisted Synthesis of Some Indole and Isoniazid Derivatives as Antitubercular Agents and Molecular Docking Study. Russ. J. Org. Chem. 56, 662–670 (2020).
- 28. Janosik, S. M. One-Pot Multicomponent Synthesis and Cytotoxic Evaluation of Novel 7-Substituted-5-(1H-Indol-3yl)Tetrazolo[1,5-a] Pyrimidine-6-Carbonitrile. NASPA J. 42, 1 (2005).
- 29. Dhuguru, J. & Skouta, R. Role of indole scaffolds as pharmacophores in the development of anti-lung cancer agents. Molecules 25, (2020).
- 30. Mousavizadeh, F., Talebizadeh, M. & Anary-Abbasinejad, M. Synthesis of new indolylpyrrole derivatives via a four-component domino reaction between arylglyoxals, acetylacetone, indole and aliphatic amines in aqueous media. Tetrahedron Lett. 59, 2970–2974 (2018).
- 31. Kumari, P. et al. Publisher Correction: Design and efficient synthesis of pyrazoline and isoxazole bridged indole C-glycoside hybrids as potential anticancer agents (Scientific Reports, (2020), 10, 1, (6660), 10.1038/s41598-020-63377-x). Sci. Rep. 10, 1–17 (2020).
- 32. Yang, A. & Li, Z. Transition-Metal-Free Aerobic Oxidative Cross-Coupling of Indoles with Arylidenemalononitriles. Synlett 31, 194–198 (2020).
ORGANİK REAKSİYONLARDA METAL İÇERMEYEN KATALİZÖR KULLANILARAK İNDOL TÜREVLERİNİN SENTEZİ
Yıl 2021,
Cilt: 45 Sayı: 3, 615 - 630, 27.09.2021
Ratnesh Das
,
Hemlata Dangi
Sushil Kashaw
Öz
Amaç: İndol türevleri azot bazlı iskeletlerden biridir ve biyolojik veya tıbbi önemi olan birçok heterosiklik bileşiğin sentezinde sıklıkla kullanılır. Birçok indol türevi bitkilerden, mantarlardan ve deniz organizmalarından doğal olarak izole edilmiştir ve farmasötik aktiviteleri nedeniyle oldukça önemlidirler. Ayrıca polimer ve boya endüstrilerinde ve tarım sektöründe de önemli rol oynarlar. İstenen kimyasal ve biyomedikal özelliklere sahip indol bazlı heterosiklik iskelet yapısının sentezi için tasarım ve metodoloji geliştirmeye ihtiyaç vardır.
Sonuç ve Tartışma: Bu derlemede, çeşitli heterosiklik yapı iskeletlerinin hazırlanması için metal içermeyen katalizörlerin kullanıldığı, tek kap çok bileşenli reaksiyonlarla indollerin son uygulamaları özetlenmiştir ve bunlara karşılık gelen biyolojik aktiviteler tartışılmıştır.
Kaynakça
- 1. Yellappa, S. An anti-Michael route for the synthesis of indole-spiro (indene-pyrrolidine) by 1,3-cycloaddition of azomethineylide with indole-derivatised olefins. J. Heterocycl. Chem. 57, 1083–1089 (2020).
- 2. Tha, S., Shakya, S., Malla, R. & Aryal, P. Prospects of Indole derivatives as methyl transfer inhibitors: Antimicrobial resistance managers. BMC Pharmacol. Toxicol. 21, 1–11 (2020).
- 3. Sayed, M. et al. Design and synthesis of novel indole derivatives with aggregation-induced emission and antimicrobial activity. J. Photochem. Photobiol. A Chem. 383, 111969 (2019).
- 4. Parle, A. & Kumar, N. Synthesis , characterization and evaluation of 3- acetylindole derivatives as potential antifungal agents. 9, 468–474 (2020).
- 5. Mo, Z. Y. et al. Electrochemically enabled functionalization of indoles or anilines for the synthesis of hexafluoroisopropoxy indole and aniline derivatives. Org. Biomol. Chem. 18, 3832–3837 (2020).
- 6. Wei, C., Zhao, L., Sun, Z., Hu, D. & Song, B. Discovery of novel indole derivatives containing dithioacetal as potential antiviral agents for plants. Pestic. Biochem. Physiol. 166, 104568 (2020).
- 7. Turner, D. N., Edwards, L., Kornienko, A., Frolova, L. V. & Rogelj, S. Synergistic action of substituted indole derivatives and clinically used antibiotics against drug-resistant bacteria. Future Microbiol. 15, 579–590 (2020).
- 8. Syahri, J., Hidayah, N., Hilma, R. & Nurohmah, B. A. www.jmolekul.com. (2020).
- 9. Zeng, L., Lin, Y. & Cui, S. Indole-N-Carboxylic Acids and Indole-N-Carboxamides in Organic Synthesis. Chem. - An Asian J. 15, 973–985 (2020).
- 10. Ganguly, N. C., Roy, S., Mondal, P. & Saha, R. An efficient one-pot organocatalytic synthesis of 9-(1H-indol-3-yl)- xanthen-4-(9H)-ones under mild aqueous micellar conditions. Tetrahedron Lett. 53, 7067–7071 (2012).
- 11. Bhattacharjee, S., Das, D. K. & Khan, A. T. Ammonium chloride-catalyzed three-component reaction for the synthesis of fused 4H-chromene derivatives in aqueous medium. Synth. 46, 73–80 (2014).
- 12. Jiang, Y. H. & Yan, C. G. Three-Component Reaction for the Convenient Synthesis of Functionalized 3-{1-[2-(1 H -Indol-3-yl)ethyl]-4,5,6,7-tetrahydro-1 H -indol-3-yl}indolin-2-ones. Synth. 48, 3057–3064 (2016).
- 13. Klenc, J. et al. Synthesis of 4-Substituted 2- ( 4-Methylpiperazino ) pyrimidines and Quinazoline Analogs as Serotonin 5-HT 2A Receptor Ligands. J. Heterocycl. Chem. 46, 1259–1265 (2009).
- 14. Fatma, S. et al. An eco-compatible multicomponent strategy for the synthesis of new 2-amino-6-(1H-indol-3-yl)-4-arylpyridine-3,5-dicarbonitriles in aqueous micellar medium promoted by thiamine-hydrochloride. Tetrahedron Lett. 55, 2201–2207 (2014).
- 15. El-Sayed, N. S. et al. Synthesis of 4-aryl-6-indolylpyridine-3-carbonitriles and evaluation of their antiproliferative activity. Tetrahedron Lett. 55, 1154–1158 (2014).
- 16. Naureen, S. et al. Synthesis of tetrasubstitutd imidazoles containing indole and their antiurease and antioxidant activities. J. Chil. Chem. Soc. 62, 3583–3587 (2017).
- 17. Chen, T., Xu, X. P. & Ji, S. J. Novel, one-pot, three-component route to indol-3-yl substituted spirooxindole derivatives. J. Comb. Chem. 12, 659–663 (2010).
- 18. Chen, X. B., Xiong, S. L., Xie, Z. X., Wang, Y. C. & Liu, W. Three-Component One-Pot Synthesis of Highly Functionalized Bis-Indole Derivatives. ACS Omega 4, 11832–11837 (2019).
- 19. Borpatra, P. J., Deka, B., Rajbongshi, B. K., Deb, M. L. & Baruah, P. K. One-pot sequential multi-component reaction: Synthesis of 3-substituted indoles. Synth. Commun. 48, 2074–2082 (2018).
- 20. Waill A, E., Ghoson M, D., Paul W, T. & Ting-Chi, W. Influence of two extraction methods on essential oils of some Apiaceae family plants. Egypt Pharm. J 18, 160–164 (2019).
- 21. Wang, L. et al. Synthesis of Diastereoenriched Oxazolo[5,4-b]indoles via Catalyst-Free Multicomponent Bicyclizations. J. Org. Chem. 82, 3605–3611 (2017).
- 22. Lin, W., Zheng, Y. X., Xun, Z., Huang, Z. Bin & Shi, D. Q. Microwave-Assisted Regioselective Synthesis of 3-Functionalized Indole Derivatives via Three-Component Domino Reaction. ACS Comb. Sci. 19, 708–713 (2017).
- 23. Zeng, L., Sajiki, H. & Cui, S. Multicomponent Ugi Reaction of Indole- N-carboxylic Acids: Expeditious Access to Indole Carboxamide Amino Amides. Org. Lett. 21, 5269–5272 (2019).
- 24. Singh, V. K., Dubey, R., Upadhyay, A., Sharma, L. K. & Singh, R. K. P. Electrochemical approach for synthesis of 3-substituted indole derivatives. Tetrahedron Lett. 58, 4227–4231 (2017).
- 25. Krishnammagari, S. K., Balwe, S. G., Kim, J. S., Lim, K. T. & Jeong, Y. T. A one-pot four-component domino protocol for the synthesis of indole and coumarin containing pyridine-3-carbonitrile derivatives. Monatshefte fur Chemie 150, 691–702 (2019).
- 26. Mazzotta, S. et al. 3-Amino-alkylated indoles: Unexplored green products acting as anti-inflammatory agents. Future Med. Chem. 12, 5–17 (2019).
- 27. Rathod, A. S., Reddy, P. V. & Biradar, J. S. Microwave-Assisted Synthesis of Some Indole and Isoniazid Derivatives as Antitubercular Agents and Molecular Docking Study. Russ. J. Org. Chem. 56, 662–670 (2020).
- 28. Janosik, S. M. One-Pot Multicomponent Synthesis and Cytotoxic Evaluation of Novel 7-Substituted-5-(1H-Indol-3yl)Tetrazolo[1,5-a] Pyrimidine-6-Carbonitrile. NASPA J. 42, 1 (2005).
- 29. Dhuguru, J. & Skouta, R. Role of indole scaffolds as pharmacophores in the development of anti-lung cancer agents. Molecules 25, (2020).
- 30. Mousavizadeh, F., Talebizadeh, M. & Anary-Abbasinejad, M. Synthesis of new indolylpyrrole derivatives via a four-component domino reaction between arylglyoxals, acetylacetone, indole and aliphatic amines in aqueous media. Tetrahedron Lett. 59, 2970–2974 (2018).
- 31. Kumari, P. et al. Publisher Correction: Design and efficient synthesis of pyrazoline and isoxazole bridged indole C-glycoside hybrids as potential anticancer agents (Scientific Reports, (2020), 10, 1, (6660), 10.1038/s41598-020-63377-x). Sci. Rep. 10, 1–17 (2020).
- 32. Yang, A. & Li, Z. Transition-Metal-Free Aerobic Oxidative Cross-Coupling of Indoles with Arylidenemalononitriles. Synlett 31, 194–198 (2020).