How to cite this paper
Waskle, A., Waskle, D., Solanki, T., Barfa, P., Sharma, P & Kumar, A. (2025). Base and additive free click chemistry strategy to accomplish the synthesis of amalgamated pyrazolo-triazole heterocyclic scaffolds and their molecular docking study.Current Chemistry Letters, 14(1), 173-182.
Refrences
1. Boyang Yin 1, Céline Croutxé-Barghorn, Christelle Delaite 1, Xavier Allonas. (2019) A new synthetic pathway based on one-pot sequential aza-Michael addition and photo CuAAC click reactions. RSC Adv., 9, 4824-4831.
2. Yang Na., Yuan G., (2018) A Multicomponent Electrosynthesis of 1,5-Disubstituted and 1-Aryl 1,2,4-Triazoles. J. Org. Chem., 83, 19, 11963–11969
3. Tornoe C. W., Christensen C., Mendal M., (2002) Peptidotriazoles on Solid Phase: [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides. J. Org. Chem., 67, 3057-3064.
4. Liang L, Astruc D., (2011) The copp er (I)-catalyzed alkyne-azide cycloaddition (CuAAC) “click” reaction and its applications. An overview. Coor. Chem. Rev.255, 2933-2945.
5. Yamada M., Matsumura M., Uchida Y., Kavahata M., Murata Y., Kakusava N., Yamaguchi K., Yasuike S., (2016) Copper-catalyzed [3 + 2] cycloaddition of (phenylethynyl)di-p-tolylstibane with organic azides. Beilstein J. Org. Chem. 12, 1309–1313.
6. Galstya S., Ghochikyan V., Frangyan R., Tamazyan A., Ayvazyan G., (2018) Synthesis of Novel Derivatives of 1,2,4-Triazoles. Chemistry select, 3, 9981-9985.
7. Cera G., Haven T., Ackermann L., (2013) Versatile reactivity of rhodium-iminocarbenes derived from N-sulfonyl triazoles. Angew. Chem., Int. Ed., 52, 1371-1373.
8. Ackermann L., Jeyachandran R., Potukuchi H. K., Novak P., Buttner L., (2010) Palladium-Catalyzed Dehydrogenative Direct Arylations of 1,2,3-Triazoles.Org. Lett., 12, 2056.
9. Li H., Wu X., Hao H., Li H., Zhao Y., Wang Y., Lian P., Zheng Y., Bao X., Wan X., (2018) [3+2] Cycloaddition of Nitrile Ylides with Diazonium Salts: Copper Catalyzed One Pot Synthesis of Fully Substituted 1,2,3-Triazoles. Org. Lett., 20, 5224-5227.
10. Bechara W. S., Khazhieva I. S., Rodriguez E., Charette A. B., (2015) One-Pot Synthesis of 3,4,5-Trisubstituted 1,2,4-Triazoles via the Addition of Hydrazides to Activated Secondary Amides. Org. Lett., 17, 1184-1187.
11. Kolb H. C., Finn M. G., Shapless K. B., (2001) Click Chemistry: Diverse Chemical Function from a Few Good Reactions. Angev. Chem. Int. Ed., 40, 2004-2021.
12. Rostovtsev V. V., Green L. G., Folkin V. V., Sharpless K. B., (2002) A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal Alkynes. Angev. Chem. Int. Ed., 41, 2596.
13. Prieto A., Uzel A., Bouyssi D., Monteiro N., (2017) Thiocyanation of N, N -Dialkylhydrazonoyl Bromides: An Entry to Sulfur-Containing 1,2,4-Triazole Derivatives.Eur. J. Org. Chem.,28, 4201-4204.
14. SzaboK. E., Pahi A., Somsak L., (2017) C-Glycosyl 1,2,4-triazoles: Synthesis of the 3-β-d-glucopyranosyl-1,5-disubstituted and 5-β-d-glucopyranosyl-1,3-disubstituted variants. Tetrahedron., 73, 3810-3822.
15. Holm S. C., Straub B. F., (2011) Synthesis of N-Substituted 1,2,4-Triazoles A Review. Org. Prep. Proced. Int., 43, 319-347.
16. Rostovtsev V. V., Green L.G., Fokin V. V., Sharpless K. B., (2002) A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal Alkynes. Angew. Chem. Int. Ed., 41, 2596-2599.
17. Johan R. J., Tamás B. S., Anna S. S., Nina K. (2016) Ruthenium-Catalyzed Azide Alkyne Cycloaddition Reaction: Scope, Mechanism, and Applications. Chem. Rev. 116, 23, 14726–14768.
18. Yang N., Yuan G., (2018) A Multicomponent Electrosynthesis of 1,5-Disubstituted and 1-Aryl 1,2,4-Triazoles. J. Org. Chem., 83, 11963-11969.
19. Bechara W. S., Khazhieva I. S., Rodriguez E., Charette A. B., (2015) One-Pot Synthesis of 3,4,5-Trisubstituted 1,2,4-Triazoles via the Addition of Hydrazides to Activated Secondary Amides. Org. Lett., 17, 1184-1187.
20. Malani H. A., Makwana A. H., Makwana H., (2017) A brief review article: Various synthesis and therapeutic importance of 1, 2, 4-triazole and its derivatives. Mor. J. Chem. 5, 41- 58.
21. Mohammad B., Rahele D., Mahdi M., Khosro J., (2017) Synthesis of new 2-substituted pyrazolo[5,1-b] [1,3] oxazoles via Sonogashira coupling reactions in water. Tetrahedron., 73, 3281-3287.
22. Fustero S., Sanchez-Rosselo M., Barrio P., Simon-FuentesA., (2011) From 2000 to mid-2010: a fruitful decade for the synthesis of pyrazoles. Chem. Rev., 111, 6984-7034.
23. Li R. Y., Li C., Li J. C., (2015) Synthesis and biological evaluation of 1,3-diaryl pyrazole derivatives as potential antibacterial and anti-inflammatory agents. Bioorg. Med. Chem. Lett., 25, 5052-5057.
24. Kamal A., Saik A., B., Jain N., (2015) Design and synthesis of pyrazole–oxindole conjugates targeting tubulin polymerization as new anticancer agents. Eur. J. Med. Chem., 92, 501-513.
25. Alegaon S., G., Alagawadi K., R., Garg M., Dushyant K., Vinod D., (2014) 1,3,4-Trisubstituted pyrazole analogues as promising anti-inflammatory agents. Bioorg. Chem., 54, 51-59.
26. Kunes J., Balsanec V., Pour M., Buchta V., (2001) Synthesis and Antifungal Activity Evaluation of 3-Hetaryl-2,5-dihydrofuran-2-ones. An Unusual Fragmentation of the Oxazole Ring via 2,3-Selenoxide Shift Czech. Chem. Commun., 66, 1809-1830.
27. Daswani U., Singh U., Sharma P., Kumar A. (2018) From Molecules to Devices: A DFT/TD-DFT Study of Dipole Moment and Internal Reorganization Energies in Opto electronically Active Aryl Azo Chromophores. J. Phys. Chem. C, 122, 14390-14401.
28. Ahuja M., Biswas S., Sharma P., Samanta S., (2018) Metal-Free Based Domino Approach to Pyrano-Fused-Pyrido[3,2,1-jk] carbazolones: Antibacterial and Molecular Docking Studies. chemistry select, 3, 4354-4360.
29. Malvia H., Kumar A., Sharma P., Mishra R., (2017) A Submicellar Liquid Chromatographic Method for Quantitative Determination of Muscle Relaxant Drug Baclofen in Solubilized System. asian journals of chemistry, 29, 1509-1514.
30. Malvia H., Sharma A., Sharma P., Mishra R., (2017) A Micellar Liquid Chromatographic Method for the Determination of Azosemide in Solubilized System. J. Surfact. Deterg, 20, 1411-1418.
31. Sharma A., Sharma P., Sharma P. K., (2017) Exploration of Antioxidant Activity of Newly Synthesized Azo Flavones and its Correlation with Electrochemical Parameters along with the Study of their Redox Behaviour. Journal of analytical chemistry, 72, 1034-1044.
32. Reen G. K., Kuma A., Sharma P., (2017) In vitro and in silico evaluation of 2-(substituted phenyl) oxazolo [4,5-b]pyridine derivatives as potential antibacterial agents. Med. Chem. Res., 26, 3336-3344.
33. Reen G. K., Ahuja M., Kumar A., Patidar R., Sharma P., (2017) ZnO Nanoparticle-Catalyzed Multicomponent Reaction for the Synthesis of 1,4Diaryl Dihydropyridines. Organic Preparation and Procedures International, 49, 273-286.
34. Reen G. K., Kumar A., Sharma P., (2019) Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage. Beilstein. J. Org. Chem., 15, 1612-1704.
35. Orazio A. A., Gianfranco F., Paolino F., Fabio M., Giada M., Francesca R. P., (2010) Copper (II)/Copper (I)-Catalyzed Aza-Michael Addition/Click Reaction of in Situ Generated α-Azidohydrazones: Synthesis of Novel Pyrazolone− Triazole Framework. Org. Lett., 12, 468-471.
36. Dresler E., Woliński P., Wróblewska A., Jasiński R., (2023) On the Question of Zwitterionic Intermediates in the [3+2] Cycloaddition Reactions between Aryl Azides and Ethyl Propiolate. Molecules, 28, 8152.
37. Maleki A., Rahimi J., Demchuk O. M., Wilczewska A. Z., Jasiński R., (2018) Green in water sonochemical synthesis of tetrazolopyrimidine derivatives by a novel core-shell magnetic nanostructure catalyst. Ultrasonics Sonochemistry, 43, 262-271.
38. Jasinski R., (2015) Nitroacetylene as dipolarophile in [2 + 3] cycloaddition reactions with allenyl-type three-atom components: DFT computational study. Monatsh Chem., 146 591–599.
39. Tornøe, C. W., Christensen, C., Meldal, M. (2002). Peptidotriazoles on Solid Phase: [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides. The Journal of Organic Chemistry, 67(9), 3057-3064. DOI: 10.1021/jo011148j.
40. Weiguo W., Yunzhi L., Yudao M., Chen-Ho T., Zhenghu X., (2018,) Copper (I)-Catalyzed three-component click/persulfuration cascade: Regioselective synthesis of triazole disulfides. Org. Lett. 20, 2956-2959.
41. Orazio A. A., Gianfranco F., Paolino F., Fabio M., Giada M., Francesca R. P. (2010) Copper (II)/Copper (I)-Catalyzed Aza-Michael Addition/Click Reaction of in Situ Generated α-Azidohydrazones: Synthesis of Novel Pyrazolone− Triazole Framework. Org. Lett., 12, 468-471.
42. Trott O., Olson A. J., (2010) AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. Journal of Computational Chemistry 31, 455-461. DOI 10.1002/jcc.21334
43. Dongamanti A. Gugulothu T. Bhukya K. K., Gundu S., Dharavath R., Thumma V., Madderla S., Bujji S., (2023) Microwave-assisted synthesis, molecular docking studies of 1,2,3-triazole-based carbazole derivatives as antimicrobial, antioxidant and anticancer agents., RSC Adv., 13, 25, DOI: 10.1039/d2ra05960frsc.li/rsc-advances
44. Jasinski R., Dresler E., (2020) On the Question of Zwitterionic Intermediates in the [3+2] Cycloaddition Reactions: A Critical Review. Organics, 1, 49–69.
2. Yang Na., Yuan G., (2018) A Multicomponent Electrosynthesis of 1,5-Disubstituted and 1-Aryl 1,2,4-Triazoles. J. Org. Chem., 83, 19, 11963–11969
3. Tornoe C. W., Christensen C., Mendal M., (2002) Peptidotriazoles on Solid Phase: [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides. J. Org. Chem., 67, 3057-3064.
4. Liang L, Astruc D., (2011) The copp er (I)-catalyzed alkyne-azide cycloaddition (CuAAC) “click” reaction and its applications. An overview. Coor. Chem. Rev.255, 2933-2945.
5. Yamada M., Matsumura M., Uchida Y., Kavahata M., Murata Y., Kakusava N., Yamaguchi K., Yasuike S., (2016) Copper-catalyzed [3 + 2] cycloaddition of (phenylethynyl)di-p-tolylstibane with organic azides. Beilstein J. Org. Chem. 12, 1309–1313.
6. Galstya S., Ghochikyan V., Frangyan R., Tamazyan A., Ayvazyan G., (2018) Synthesis of Novel Derivatives of 1,2,4-Triazoles. Chemistry select, 3, 9981-9985.
7. Cera G., Haven T., Ackermann L., (2013) Versatile reactivity of rhodium-iminocarbenes derived from N-sulfonyl triazoles. Angew. Chem., Int. Ed., 52, 1371-1373.
8. Ackermann L., Jeyachandran R., Potukuchi H. K., Novak P., Buttner L., (2010) Palladium-Catalyzed Dehydrogenative Direct Arylations of 1,2,3-Triazoles.Org. Lett., 12, 2056.
9. Li H., Wu X., Hao H., Li H., Zhao Y., Wang Y., Lian P., Zheng Y., Bao X., Wan X., (2018) [3+2] Cycloaddition of Nitrile Ylides with Diazonium Salts: Copper Catalyzed One Pot Synthesis of Fully Substituted 1,2,3-Triazoles. Org. Lett., 20, 5224-5227.
10. Bechara W. S., Khazhieva I. S., Rodriguez E., Charette A. B., (2015) One-Pot Synthesis of 3,4,5-Trisubstituted 1,2,4-Triazoles via the Addition of Hydrazides to Activated Secondary Amides. Org. Lett., 17, 1184-1187.
11. Kolb H. C., Finn M. G., Shapless K. B., (2001) Click Chemistry: Diverse Chemical Function from a Few Good Reactions. Angev. Chem. Int. Ed., 40, 2004-2021.
12. Rostovtsev V. V., Green L. G., Folkin V. V., Sharpless K. B., (2002) A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal Alkynes. Angev. Chem. Int. Ed., 41, 2596.
13. Prieto A., Uzel A., Bouyssi D., Monteiro N., (2017) Thiocyanation of N, N -Dialkylhydrazonoyl Bromides: An Entry to Sulfur-Containing 1,2,4-Triazole Derivatives.Eur. J. Org. Chem.,28, 4201-4204.
14. SzaboK. E., Pahi A., Somsak L., (2017) C-Glycosyl 1,2,4-triazoles: Synthesis of the 3-β-d-glucopyranosyl-1,5-disubstituted and 5-β-d-glucopyranosyl-1,3-disubstituted variants. Tetrahedron., 73, 3810-3822.
15. Holm S. C., Straub B. F., (2011) Synthesis of N-Substituted 1,2,4-Triazoles A Review. Org. Prep. Proced. Int., 43, 319-347.
16. Rostovtsev V. V., Green L.G., Fokin V. V., Sharpless K. B., (2002) A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal Alkynes. Angew. Chem. Int. Ed., 41, 2596-2599.
17. Johan R. J., Tamás B. S., Anna S. S., Nina K. (2016) Ruthenium-Catalyzed Azide Alkyne Cycloaddition Reaction: Scope, Mechanism, and Applications. Chem. Rev. 116, 23, 14726–14768.
18. Yang N., Yuan G., (2018) A Multicomponent Electrosynthesis of 1,5-Disubstituted and 1-Aryl 1,2,4-Triazoles. J. Org. Chem., 83, 11963-11969.
19. Bechara W. S., Khazhieva I. S., Rodriguez E., Charette A. B., (2015) One-Pot Synthesis of 3,4,5-Trisubstituted 1,2,4-Triazoles via the Addition of Hydrazides to Activated Secondary Amides. Org. Lett., 17, 1184-1187.
20. Malani H. A., Makwana A. H., Makwana H., (2017) A brief review article: Various synthesis and therapeutic importance of 1, 2, 4-triazole and its derivatives. Mor. J. Chem. 5, 41- 58.
21. Mohammad B., Rahele D., Mahdi M., Khosro J., (2017) Synthesis of new 2-substituted pyrazolo[5,1-b] [1,3] oxazoles via Sonogashira coupling reactions in water. Tetrahedron., 73, 3281-3287.
22. Fustero S., Sanchez-Rosselo M., Barrio P., Simon-FuentesA., (2011) From 2000 to mid-2010: a fruitful decade for the synthesis of pyrazoles. Chem. Rev., 111, 6984-7034.
23. Li R. Y., Li C., Li J. C., (2015) Synthesis and biological evaluation of 1,3-diaryl pyrazole derivatives as potential antibacterial and anti-inflammatory agents. Bioorg. Med. Chem. Lett., 25, 5052-5057.
24. Kamal A., Saik A., B., Jain N., (2015) Design and synthesis of pyrazole–oxindole conjugates targeting tubulin polymerization as new anticancer agents. Eur. J. Med. Chem., 92, 501-513.
25. Alegaon S., G., Alagawadi K., R., Garg M., Dushyant K., Vinod D., (2014) 1,3,4-Trisubstituted pyrazole analogues as promising anti-inflammatory agents. Bioorg. Chem., 54, 51-59.
26. Kunes J., Balsanec V., Pour M., Buchta V., (2001) Synthesis and Antifungal Activity Evaluation of 3-Hetaryl-2,5-dihydrofuran-2-ones. An Unusual Fragmentation of the Oxazole Ring via 2,3-Selenoxide Shift Czech. Chem. Commun., 66, 1809-1830.
27. Daswani U., Singh U., Sharma P., Kumar A. (2018) From Molecules to Devices: A DFT/TD-DFT Study of Dipole Moment and Internal Reorganization Energies in Opto electronically Active Aryl Azo Chromophores. J. Phys. Chem. C, 122, 14390-14401.
28. Ahuja M., Biswas S., Sharma P., Samanta S., (2018) Metal-Free Based Domino Approach to Pyrano-Fused-Pyrido[3,2,1-jk] carbazolones: Antibacterial and Molecular Docking Studies. chemistry select, 3, 4354-4360.
29. Malvia H., Kumar A., Sharma P., Mishra R., (2017) A Submicellar Liquid Chromatographic Method for Quantitative Determination of Muscle Relaxant Drug Baclofen in Solubilized System. asian journals of chemistry, 29, 1509-1514.
30. Malvia H., Sharma A., Sharma P., Mishra R., (2017) A Micellar Liquid Chromatographic Method for the Determination of Azosemide in Solubilized System. J. Surfact. Deterg, 20, 1411-1418.
31. Sharma A., Sharma P., Sharma P. K., (2017) Exploration of Antioxidant Activity of Newly Synthesized Azo Flavones and its Correlation with Electrochemical Parameters along with the Study of their Redox Behaviour. Journal of analytical chemistry, 72, 1034-1044.
32. Reen G. K., Kuma A., Sharma P., (2017) In vitro and in silico evaluation of 2-(substituted phenyl) oxazolo [4,5-b]pyridine derivatives as potential antibacterial agents. Med. Chem. Res., 26, 3336-3344.
33. Reen G. K., Ahuja M., Kumar A., Patidar R., Sharma P., (2017) ZnO Nanoparticle-Catalyzed Multicomponent Reaction for the Synthesis of 1,4Diaryl Dihydropyridines. Organic Preparation and Procedures International, 49, 273-286.
34. Reen G. K., Kumar A., Sharma P., (2019) Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage. Beilstein. J. Org. Chem., 15, 1612-1704.
35. Orazio A. A., Gianfranco F., Paolino F., Fabio M., Giada M., Francesca R. P., (2010) Copper (II)/Copper (I)-Catalyzed Aza-Michael Addition/Click Reaction of in Situ Generated α-Azidohydrazones: Synthesis of Novel Pyrazolone− Triazole Framework. Org. Lett., 12, 468-471.
36. Dresler E., Woliński P., Wróblewska A., Jasiński R., (2023) On the Question of Zwitterionic Intermediates in the [3+2] Cycloaddition Reactions between Aryl Azides and Ethyl Propiolate. Molecules, 28, 8152.
37. Maleki A., Rahimi J., Demchuk O. M., Wilczewska A. Z., Jasiński R., (2018) Green in water sonochemical synthesis of tetrazolopyrimidine derivatives by a novel core-shell magnetic nanostructure catalyst. Ultrasonics Sonochemistry, 43, 262-271.
38. Jasinski R., (2015) Nitroacetylene as dipolarophile in [2 + 3] cycloaddition reactions with allenyl-type three-atom components: DFT computational study. Monatsh Chem., 146 591–599.
39. Tornøe, C. W., Christensen, C., Meldal, M. (2002). Peptidotriazoles on Solid Phase: [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides. The Journal of Organic Chemistry, 67(9), 3057-3064. DOI: 10.1021/jo011148j.
40. Weiguo W., Yunzhi L., Yudao M., Chen-Ho T., Zhenghu X., (2018,) Copper (I)-Catalyzed three-component click/persulfuration cascade: Regioselective synthesis of triazole disulfides. Org. Lett. 20, 2956-2959.
41. Orazio A. A., Gianfranco F., Paolino F., Fabio M., Giada M., Francesca R. P. (2010) Copper (II)/Copper (I)-Catalyzed Aza-Michael Addition/Click Reaction of in Situ Generated α-Azidohydrazones: Synthesis of Novel Pyrazolone− Triazole Framework. Org. Lett., 12, 468-471.
42. Trott O., Olson A. J., (2010) AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. Journal of Computational Chemistry 31, 455-461. DOI 10.1002/jcc.21334
43. Dongamanti A. Gugulothu T. Bhukya K. K., Gundu S., Dharavath R., Thumma V., Madderla S., Bujji S., (2023) Microwave-assisted synthesis, molecular docking studies of 1,2,3-triazole-based carbazole derivatives as antimicrobial, antioxidant and anticancer agents., RSC Adv., 13, 25, DOI: 10.1039/d2ra05960frsc.li/rsc-advances
44. Jasinski R., Dresler E., (2020) On the Question of Zwitterionic Intermediates in the [3+2] Cycloaddition Reactions: A Critical Review. Organics, 1, 49–69.