{"doi":"10.1002/chem.202301888","title":"Heterocyclic Merging of Stereochemically Diverse Chiral Piperazines and Morpholines with Indazoles","abstract":"We report a heterocyclic merging approach to construct novel indazolo-piperazines and indazolo-morpholines. Starting from chiral diamines and amino alcohols, novel regiochemically (1,3 and 1,4) and stereochemically diverse (relative and absolute) cohorts of indazolo-piperazines and indazolo-morpholines were obtained within six or seven steps. The key transformations involved are a Smiles rearrangement to generate the indazole core structure and a late-stage Michael addition to build the piperazine and morpholine heterocycles. We further explored additional vector diversity by incorporating substitutions on the indazole aromatic ring, generating a total of 20 unique, enantiomerically pure heterocyclic scaffolds.","journal":"Chemistry - A European Journal","year":2023,"id":382204,"datarank":0.20794415416798362,"base_score":1.3862943611198906,"endowment":1.3862943611198906,"self_citation_contribution":0.20794415416798362,"citation_network_contribution":0.0,"self_endowment_contribution":0.20794415416798362,"citer_contribution":0.0,"corpus_percentile":null,"corpus_rank":null,"citation_count":3,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9504,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2023-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":1148420,"name":"Timothy M. Mansfield","orcid":"0000-0001-5749-3588","position":1,"is_corresponding":false},{"id":488320,"name":"Kevin Tran","orcid":"0000-0002-2579-8907","position":2,"is_corresponding":false},{"id":554791,"name":"Evan Lenkeit","orcid":null,"position":3,"is_corresponding":false},{"id":506397,"name":"Kevin R. MacKenzie","orcid":"0000-0001-9620-5868","position":4,"is_corresponding":false},{"id":513440,"name":"Damian W. Young","orcid":"0000-0002-1595-9658","position":5,"is_corresponding":false},{"id":565977,"name":"Srinivas Chamakuri","orcid":"0000-0002-7586-4992","position":6,"is_corresponding":false},{"id":1148419,"name":"Amol B. Viveki","orcid":"0000-0002-7805-8160","position":0,"is_corresponding":true}],"reference_count":29,"raw_metadata":{"citation_network_status":"fetched"},"created_at":"2026-07-19T01:17:17.113710Z","pmid":"37462979","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":[]}