{"doi":"10.1021/ol0600638","title":"Enediynes from Aza-Enediynes:  <i>C</i>,<i>N</i>-Dialkynyl Imines Undergo Both Aza-Bergman Rearrangement and Conversion to Enediynes and Fumaronitriles","abstract":null,"journal":"Organic Letters","year":2006,"id":688399,"datarank":0.4943755299006494,"base_score":3.295836866004329,"endowment":3.295836866004329,"self_citation_contribution":0.4943755299006494,"citation_network_contribution":0.0,"self_endowment_contribution":0.4943755299006494,"citer_contribution":0.0,"corpus_percentile":null,"corpus_rank":null,"citation_count":26,"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":1501220,"name":"Aibin Zhang","orcid":"0009-0006-6245-1423","position":1,"is_corresponding":false},{"id":1306309,"name":"Sean M. Kerwin","orcid":"0000-0001-8432-6558","position":2,"is_corresponding":false},{"id":275336,"name":"Liping Feng","orcid":"0000-0002-2936-7397","position":0,"is_corresponding":false}],"reference_count":0,"raw_metadata":{"has_enrichment":true,"resolved":true,"title":"Enediynes from Aza-Enediynes:  <i>C</i>,<i>N</i>-Dialkynyl Imines Undergo Both Aza-Bergman Rearrangement and Conversion to Enediynes and Fumaronitriles","abstract":"[reaction; see text] Aza-enediynes (C,N-dialkynyl imines) undergo thermal aza-Bergman rearrangement to beta-alkynyl acrylonitriles through 2,5-didehydropyridine (2,5-ddp) intermediates. Certain aza-enediynes also undergo an alternative process affording enediynes and fumaronitriles. Studies employing a specifically (l3)C-labeled aza-enediyne show that the conversion to enediyne is second order in aza-enediyne, proceeds by a \"head-to-tail\" coupling, and affords the (Z)-enediyne.","is_dataset_classified":null,"base_score":3.295836866004329,"endowment":3.295836866004329,"datacite_reuse_total":0,"file_count":0,"downloads":0,"views":0,"has_version_chain":false,"is_dataset":false,"is_oa":false,"pmid":"16671762","pmcid":null,"openalex_id":"https://openalex.org/W2952637116","authors":[],"funders":[{"funder_name":"NIEHS NIH HHS","grant_id":"P30 ES07784","title":null}],"total_grants":1,"fwci":1.4499,"citation_percentile":0.81459071,"influential_citations":0,"citation_trend":[{"year":2012,"count":1},{"year":2013,"count":1},{"year":2014,"count":1},{"year":2016,"count":1},{"year":2021,"count":2},{"year":2022,"count":1},{"year":2023,"count":2},{"year":2024,"count":2}],"oa_status":"closed","license":null,"oa_locations":[{"url":"https://pubs.acs.org/doi/pdf/10.1021/ol0600638","host_type":"publisher"},{"url":"https://doi.org/10.1021/ol0600638","host_type":"journal"},{"url":"https://pubmed.ncbi.nlm.nih.gov/16671762","host_type":"repository"}],"fields_of_study":["Cyclization and Aryne Chemistry","Catalytic Alkyne Reactions","Chemical synthesis and alkaloids","Chemistry","Medicine","Aza Compounds","Cyclization","Enediynes","Imines","Molecular Structure","Nitriles"],"mesh_terms":["Aza Compounds","Cyclization","Imines","Nitriles","Molecular Structure","Enediynes"],"keywords":["Chemistry","Enediyne","Stereochemistry","Combinatorial chemistry"],"sdg_mappings":[],"linked_datasets":[],"clinical_trials":[],"software_tools":[],"database_accessions":[],"source":"live","citation_network_status":"fetched"},"created_at":"2026-08-19T15:49:40.414406Z","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":[]}