{"doi":"10.1002/poc.610061102","title":"A reinvestigation of the reactions between diazomethane and 1‐phenylurazole","abstract":"<jats:title>Abstract</jats:title><jats:p>Exhaustive methylation of 1‐phenylurazole (1), using ethereal diazomethane as the methylating agent, results in the formation of three products: 1‐phenyl‐3,5‐dimethoxy‐1,2,4‐triazole (2), 1‐phenyl‐3‐methoxy‐4‐methyl‐Δ<jats:sup>2</jats:sup>‐1,2,4‐triazolinev5‐one (3) and 1‐phenyl‐2,4‐dimethylurazole (4). Based on the amounts of 2–4 isolated, the overall yields in these reactions are typically &gt;90%. When 1 and diazomethane were allowed to react in a fashion that resulted in the formation of monomethylated analogues of 1, 1‐phenyl‐3‐methoxy‐Δ<jats:sup>2</jats:sup>‐1,2,4‐triazoline‐5‐one (5) and 1‐phenylv2‐methylurazole (6) were formed. In separate experiments, the monomethylated species 5 and 6 were allowed to react with diazomethane in efforts to develop a sequence of reactions that reasonably accounts for the formation of 2–4. Whereas <jats:italic>N</jats:italic>‐ and <jats:italic>O</jats:italic>‐methylated products were obtained when 5 was treated with ethereal diazomethane, the reaction of 6 and diazomethane produced only the <jats:italic>N</jats:italic>‐alkylated product 1‐phenyl–2,4‐dimethylurazole (in quantitative yield). The outcomes of these experiments are consistent with a sequence of reactions in which the treatment of 1 with diazomethane results, initially, in the formation of the monomethylated species 5 and 6. In the presence of sufficient diazomethane, 5 and 6 then undergo further mothylation, forming the dimethylated species 2–4.</jats:p>","journal":"Journal of Physical Organic Chemistry","year":1993,"id":34847,"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":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":179736,"name":"L.‐H. Wang","orcid":null,"position":1,"is_corresponding":false},{"id":179735,"name":"M. J. Bausch","orcid":null,"position":0,"is_corresponding":false}],"reference_count":0,"raw_metadata":{"has_enrichment":true,"base_score":0.0,"endowment":0.0,"datacite_reuse_total":0,"file_count":0,"downloads":0,"views":0,"has_version_chain":false,"is_dataset":false,"is_oa":false,"pmid":"24523987","pmcid":null,"openalex_id":"https://openalex.org/W2070031917","authors":[],"funders":[],"total_grants":0,"fwci":0.0,"citation_percentile":0.1656225,"influential_citations":0,"citation_trend":[],"oa_status":"closed","license":"http://onlinelibrary.wiley.com/termsAndConditions#vor","oa_locations":[{"url":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fpoc.610061102","host_type":"publisher"},{"url":"https://onlinelibrary.wiley.com/doi/pdf/10.1002/poc.610061102","host_type":"publisher"},{"url":"https://doi.org/10.1002/poc.610061102","host_type":"journal"}],"fields_of_study":["Synthesis and Biological Evaluation","Click Chemistry and Applications","Chemistry"],"mesh_terms":[],"keywords":["Diazomethane","Chemistry","Methylation","Yield (engineering)","Alkylation","Organic chemistry","Medicinal chemistry","Stereochemistry","Catalysis"],"sdg_mappings":[],"linked_datasets":[],"clinical_trials":[],"software_tools":[],"database_accessions":[],"source":"live","citation_network_status":"fetched"},"created_at":"2026-06-09T20:37:23.382757Z","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":[]}