Triazole-containing compounds have shown great biological activity ranging from antiviral, antibacterial, to anticancer, to name a few. Coumarin derivatives have also shown interesting biological activities. The combination of these bioactive compounds appears to have great promise for new and future medicines. In this work, various 4-azido-coumarins were synthesized via the transformation of the 4-hydroxy derivatives to 4-benzotriazolyloxy coumarins by reaction with the peptide coupling agent (benzotriazol-1-yloxy)tris-(dimethylamino)phosphonium hexafluorophosphate (BOP), and 1,8-diazabicycloundec-7-ene (DBU) as the base, in tetrahydrofuran (THF) solvent. The 4-benzotriazolyloxy coumarins were converted to the 4-azidocoumarins by reaction with sodium azide (NaN3), and the overall process was simplified to a one-pot, two-step process. The methodology reduced the need for additional manipulations and purifications. Using the 4-azidocoumarins thus prepared, the 1,4-disubstituted-1,2,3 triazoles were synthesized via a copper-catalyzed alkyne-azide cycloaddition (CuAAC) reaction. CuAAC reactions of the azides were optimized by screening of various copper catalysts 6 and copper tetrakis acetonitrile hexafluorophosphate ([Cu(CH3CN)4]PF6) gave the best results in the experiments performed. Once the reaction conditions were optimized, various 4-(1,2,3-triazolyl) coumarins were synthesized in good to excellent yields.
","abstract_html":"<p>Triazole-containing compounds have shown great biological activity ranging from antiviral, antibacterial, to anticancer, to name a few. Coumarin derivatives have also shown interesting biological activities. The combination of these bioactive compounds appears to have great promise for new and future medicines. In this work, various 4-azido-coumarins were synthesized via the transformation of the 4-hydroxy derivatives to 4-benzotriazolyloxy coumarins by reaction with the peptide coupling agent (benzotriazol-1-yloxy)tris-(dimethylamino)phosphonium hexafluorophosphate (BOP), and 1,8-diazabicycloundec-7-ene (DBU) as the base, in tetrahydrofuran (THF) solvent. The 4-benzotriazolyloxy coumarins were converted to the 4-azidocoumarins by reaction with sodium azide (NaN3), and the overall process was simplified to a one-pot, two-step process. The methodology reduced the need for additional manipulations and purifications. Using the 4-azidocoumarins thus prepared, the 1,4-disubstituted-1,2,3 triazoles were synthesized via a copper-catalyzed alkyne-azide cycloaddition (CuAAC) reaction. CuAAC reactions of the azides were optimized by screening of various copper catalysts 6 and copper tetrakis acetonitrile hexafluorophosphate ([Cu(CH3CN)4]PF6) gave the best results in the experiments performed. Once the reaction conditions were optimized, various 4-(1,2,3-triazolyl) coumarins were synthesized in good to excellent yields.</p>","abstract_has_math":false,"creators":["Netsuri, Anthony J"],"institution":null,"degree_name":"Master of Science (M.S.)","degree_level":"Thesis","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":["Mahesh Lakshman"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2013,"date_issued":"2013-01-01T08:00:00Z","date_published":"2013-01-01T08:00:00Z","updated_at":"2026-07-24T01:56:59Z","subjects":["Coumarins","triazoles","azides","Biochemistry","Biochemistry, Biophysics, and Structural Biology","Chemical Engineering"],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://academicworks.cuny.edu/cc_etds_theses/520","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Mahesh Lakshman"]},{"key":"dc:creator","label":"Author","values":["Netsuri, Anthony J"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.available","label":"Dc Date Available","values":["2016-01-06T08:00:00Z"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Thesis"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Master of Science (M.S.)"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Coumarins","triazoles","azides","Biochemistry","Biochemistry, Biophysics, and Structural Biology","Chemical Engineering"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://academicworks.cuny.edu/cc_etds_theses/520"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["Triazole-containing compounds have shown great biological activity ranging from antiviral, antibacterial, to anticancer, to name a few. Coumarin derivatives have also shown interesting biological activities. The combination of these bioactive compounds appears to have great promise for new and future medicines. In this work, various 4-azido-coumarins were synthesized via the transformation of the 4-hydroxy derivatives to 4-benzotriazolyloxy coumarins by reaction with the peptide coupling agent (benzotriazol-1-yloxy)tris-(dimethylamino)phosphonium hexafluorophosphate (BOP), and 1,8-diazabicycloundec-7-ene (DBU) as the base, in tetrahydrofuran (THF) solvent. The 4-benzotriazolyloxy coumarins were converted to the 4-azidocoumarins by reaction with sodium azide (NaN3), and the overall process was simplified to a one-pot, two-step process. The methodology reduced the need for additional manipulations and purifications. Using the 4-azidocoumarins thus prepared, the 1,4-disubstituted-1,2,3 triazoles were synthesized via a copper-catalyzed alkyne-azide cycloaddition (CuAAC) reaction. CuAAC reactions of the azides were optimized by screening of various copper catalysts 6 and copper tetrakis acetonitrile hexafluorophosphate ([Cu(CH3CN)4]PF6) gave the best results in the experiments performed. Once the reaction conditions were optimized, various 4-(1,2,3-triazolyl) coumarins were synthesized in good to excellent yields.
"]},{"key":"dc:title","label":"Title","values":["Synthesis of 4-Azidocoumarins and Their Use in Copper-Catalyzed Azide-Alkyne Cycloaddition reactions"]}]}],"canonical_facts":{"dc:contributor":["Mahesh Lakshman"],"dc:creator":["Netsuri, Anthony J"],"dc:date.available":["2016-01-06T08:00:00Z"],"dc:description.abstract":["Triazole-containing compounds have shown great biological activity ranging from antiviral, antibacterial, to anticancer, to name a few. Coumarin derivatives have also shown interesting biological activities. The combination of these bioactive compounds appears to have great promise for new and future medicines. In this work, various 4-azido-coumarins were synthesized via the transformation of the 4-hydroxy derivatives to 4-benzotriazolyloxy coumarins by reaction with the peptide coupling agent (benzotriazol-1-yloxy)tris-(dimethylamino)phosphonium hexafluorophosphate (BOP), and 1,8-diazabicycloundec-7-ene (DBU) as the base, in tetrahydrofuran (THF) solvent. The 4-benzotriazolyloxy coumarins were converted to the 4-azidocoumarins by reaction with sodium azide (NaN3), and the overall process was simplified to a one-pot, two-step process. The methodology reduced the need for additional manipulations and purifications. Using the 4-azidocoumarins thus prepared, the 1,4-disubstituted-1,2,3 triazoles were synthesized via a copper-catalyzed alkyne-azide cycloaddition (CuAAC) reaction. CuAAC reactions of the azides were optimized by screening of various copper catalysts 6 and copper tetrakis acetonitrile hexafluorophosphate ([Cu(CH3CN)4]PF6) gave the best results in the experiments performed. Once the reaction conditions were optimized, various 4-(1,2,3-triazolyl) coumarins were synthesized in good to excellent yields.
"],"dc:identifier":["https://academicworks.cuny.edu/cc_etds_theses/520"],"dc:subject":["Coumarins","triazoles","azides","Biochemistry","Biochemistry, Biophysics, and Structural Biology","Chemical Engineering"],"dc:title":["Synthesis of 4-Azidocoumarins and Their Use in Copper-Catalyzed Azide-Alkyne Cycloaddition reactions"],"thesis:degree_discipline":["Chemistry"],"thesis:degree_level":["Thesis"],"thesis:degree_name":["Master of Science (M.S.)"]},"updated_at":"2026-07-24T01:56:59Z"}