{"doi":"10.1039/c9cc09194g","title":"‘Atypical Ugi’ tetrazoles","abstract":"Amino acid-derived isocyano amides together with TMSN3, oxocomponents and 1° or 2° amines are common substrates in the Ugi tetrazole reaction. We surprisingly found that combining these substrates gives two different constitutional isomeric Ugi products A and B. A is the expected classical Ugi product whereas B is an isomeric product ('atypical Ugi') of the same molecular weight with the tetrazole heterocycle migrated to a different position. We synthesized, separated and characterized 22 different isomorphic examples of the two constitutional isomers of the Ugi reaction to unambiguously prove the formation of A and B. Mechanistic studies resulted in a proposed mechanism for the concomitant formation of A and B.","journal":"Chemical Communications","year":2020,"id":82498,"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":12,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9554,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2020-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":427128,"name":"Imogen Goodwin","orcid":null,"position":1,"is_corresponding":false},{"id":305445,"name":"Shabnam Shaabani","orcid":"0000-0001-5546-7140","position":2,"is_corresponding":false},{"id":427129,"name":"Michel P. de Haan","orcid":null,"position":3,"is_corresponding":false},{"id":420462,"name":"Katarzyna Kurpiewska","orcid":"0000-0002-6102-313X","position":4,"is_corresponding":false},{"id":420463,"name":"Justyna Kalinowska‐Tłuścik","orcid":"0000-0001-7714-1651","position":5,"is_corresponding":false},{"id":230785,"name":"Alexander Dömlingꝉ","orcid":"0000-0002-9923-8873","position":6,"is_corresponding":false},{"id":425750,"name":"Eman M. M. Abdelraheem","orcid":"0000-0002-9008-2729","position":0,"is_corresponding":true}],"reference_count":32,"raw_metadata":null,"created_at":"2026-07-18T21:53:48.608934Z","pmid":"31950120","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":[]}