{"doi":"10.1002/chem.202100929","title":"Programmed Multiple C‐H Bond Functionalization of the Privileged 4‐hydroxyquinoline Template","abstract":"<jats:title>Abstract</jats:title>\n                  <jats:p>\n                    The introduction of substituents on bare heterocyclic scaffolds can selectively be achieved by directed C−H functionalization. However, such methods have only occasionally been used, in an iterative manner, to decorate various positions of a medicinal scaffold to build chemical libraries. We herein report the multiple, site selective, metal‐catalyzed C−H functionalization of a “programmed” 4‐hydroxyquinoline. This medicinally privileged template indeed possesses multiple reactive sites for diversity‐oriented functionalization, of which four were targeted. The C‐2 and C‐8 decorations were directed by an\n                    <jats:italic>N</jats:italic>\n                    ‐oxide, before taking benefit of an\n                    <jats:italic>O</jats:italic>\n                    ‐carbamoyl protection at C‐4 to perform a Fries rearrangement and install a carboxamide at C‐3. This also released the carbonyl group of 4‐quinolones, the ultimate directing group to functionalize position 5. Our study highlights the power of multiple C−H functionalization to generate diversity in a biologically relevant library, after showing its strong antimalarial potential.\n                  </jats:p>","journal":"Chemistry – A European Journal","year":2021,"id":17457,"datarank":0.12753908122302995,"base_score":0.6931471805599453,"endowment":0.6931471805599453,"self_citation_contribution":0.10397207708399181,"citation_network_contribution":0.02356700413903814,"self_endowment_contribution":0.10397207708399181,"citer_contribution":0.02356700413903814,"corpus_percentile":null,"corpus_rank":null,"citation_count":1,"citer_count":1,"citers_with_citation_signal":1,"citers_with_endowment":1,"datacite_reuse_total":3,"is_dataset":false,"is_dataset_confidence":null,"is_data_producer":false,"deposit_databanks":null,"is_oa":false,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":null,"fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":107697,"name":"Wei Zhang","orcid":"0000-0002-4700-2658","position":1,"is_corresponding":false},{"id":124826,"name":"Nicolas Casaretto","orcid":"0000-0003-0636-983X","position":2,"is_corresponding":false},{"id":124827,"name":"Elisabeth Mouray","orcid":"0000-0001-7575-4032","position":3,"is_corresponding":false},{"id":124828,"name":"Isabelle Florent","orcid":"0000-0002-7140-6417","position":4,"is_corresponding":false},{"id":124829,"name":"Bastien Nay","orcid":"0000-0002-1209-1830","position":5,"is_corresponding":false},{"id":124825,"name":"Quentin Ronzon","orcid":"0000-0002-8635-041X","position":0,"is_corresponding":false}],"reference_count":0,"raw_metadata":{"has_enrichment":true,"base_score":0.6931471805599453,"endowment":0.6931471805599453,"datacite_reuse_total":3,"file_count":0,"downloads":0,"views":0,"has_version_chain":false,"is_dataset":false,"is_oa":false,"pmid":"33848033","pmcid":null,"openalex_id":"https://openalex.org/W3155560266","authors":[],"funders":[{"funder_name":"Labex Charmmmat","grant_id":"","title":null},{"funder_name":"Labex Charmmmat","grant_id":"","title":null}],"total_grants":2,"fwci":0.1091,"citation_percentile":0.40577246,"influential_citations":0,"citation_trend":[{"year":2023,"count":1}],"oa_status":"closed","license":"http://onlinelibrary.wiley.com/termsAndConditions#vor","oa_locations":[{"url":"https://hal.archives-ouvertes.fr/hal-03256641/file/manuscript%20for%20ChemRxiv.pdf","host_type":"GREEN"},{"url":"https://onlinelibrary.wiley.com/doi/pdf/10.1002/chem.202100929","host_type":"publisher"},{"url":"https://onlinelibrary.wiley.com/doi/full-xml/10.1002/chem.202100929","host_type":"publisher"},{"url":"https://chemistry-europe.onlinelibrary.wiley.com/doi/pdf/10.1002/chem.202100929","host_type":"publisher"},{"url":"https://doi.org/10.1002/chem.202100929","host_type":"journal"},{"url":"https://pubmed.ncbi.nlm.nih.gov/33848033","host_type":"repository"},{"url":"https://hal.science/hal-03256641","host_type":"repository"}],"fields_of_study":["Catalytic C–H Functionalization Methods","Synthesis and Catalytic Reactions","Cyclopropane Reaction Mechanisms","Medicine","Chemistry"],"mesh_terms":[],"keywords":["Surface modification","Combinatorial chemistry","Chemistry","Stereochemistry","Antimalarial Drugs","Directing Groups","Divergent Synthesis","Compound Library","C−h Bond Functionalization"],"sdg_mappings":[{"sdg_number":0,"sdg_label":"Life in Land"}],"linked_datasets":[{"doi":"10.5517/ccdc.csd.cc27g7hg","title":"CCDC 2069265: Experimental Crystal Structure Determination","publisher":"Cambridge Crystallographic Data Centre","resource_type":"Dataset"},{"doi":"10.5517/ccdc.csd.cc26kcfl","title":"CCDC 2042479: Experimental Crystal Structure Determination","publisher":"Cambridge Crystallographic Data Centre","resource_type":"Dataset"},{"doi":"10.5517/ccdc.csd.cc26kcdk","title":"CCDC 2042478: Experimental Crystal Structure Determination","publisher":"Cambridge Crystallographic Data Centre","resource_type":"Dataset"}],"clinical_trials":[],"software_tools":[],"database_accessions":[],"source":"live","citation_network_status":"fetched"},"created_at":"2026-06-02T19:00:44.449502Z","pmid":null,"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":[]}