{"doi":"10.3762/bjoc.21.194","title":"Pentacyclic aromatic heterocycles from Pd-catalyzed annulation of 1,5-diaryl-1,2,3-triazoles","abstract":"A series of pentacyclic aromatic heterocycles representing functionalized phenanthridines, naphthyridines, and phenanthrolines were prepared via Pd-catalyzed annulation of 1,5-diaryl-1,2,3-triazoles. Analogs with triazole N1-connected ortho -bromobenzene subunits successfully underwent annulation under microwave irradiation in yields of 31–90%. In contrast, annulations of triazole C1-connected ortho -bromobenzene subunit analogs failed under microwave irradiation but were successful using conventional thermal heating in yields of 31–65%. The expanded nature of the aromatic ring system following annulation was reflected by the downfield shifting of aromatic 1 H NMR signals and the red-shifting of UV–visible absorbance signals relative to their non-annulated counterparts. Structural rigidity of annulated systems compared to non-annulated counterparts was reflected by emission signals with increased intensity and decreased Stokes shifts. Five benzotriazolophenanthroline regioisomers sharing structural similarity regarding N center placement showed antimicrobial activity, as measured by minimum inhibitory concentration assays. MIC values of 2–16 μM towards Gram-positive bacteria Staphylococcus epidermidis and Bacillus subtilis and 8–16 μM towards Saccharomyces cerevisiae yeast were observed for these annulated molecules, while their analogous non-annulated control compounds were not bioactive.","journal":"Beilstein Journal of Organic Chemistry","year":2025,"id":581022,"datarank":0.0,"base_score":0.0,"endowment":0.0,"self_citation_contribution":0.0,"citation_network_contribution":0.0,"self_endowment_contribution":0.0,"citer_contribution":0.0,"corpus_percentile":null,"corpus_rank":null,"citation_count":0,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.943,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2025-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":1492417,"name":"Emily M Hanneken","orcid":null,"position":1,"is_corresponding":false},{"id":1492051,"name":"Katelyn R Grzelak","orcid":"0009-0004-0232-5754","position":2,"is_corresponding":false},{"id":1492052,"name":"J. T. FLETCHER","orcid":"0000-0003-3389-3522","position":3,"is_corresponding":false},{"id":1492416,"name":"Kaylen D Lathrum","orcid":null,"position":0,"is_corresponding":true}],"reference_count":54,"raw_metadata":null,"created_at":"2026-07-19T02:58:43.046112Z","pmid":"41256239","pmcid":null,"fwci":null,"citation_percentile":null,"influential_citations":0,"oa_status":null,"license":null,"views":0,"total_file_size_bytes":0,"version_count":0,"fair_f":null,"fair_a":null,"fair_i":null,"fair_r":null,"fair_zscore":null,"fair_rationale":null,"fair_model":null,"fair_agent_version":null,"fair_fulltext_source":null,"fair_has_llm":null,"fair_computed_at":null,"clinical_trials":[],"software_tools":[],"db_accessions":[],"linked_datasets":[],"topics":[]}