Base-Catalyzed Phenol-Mannich Condensation of Preformed Cesium Iminodiacetate. The Direct Synthesis of Calcein Blue AM and Related Acyloxymethyl Esters

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dc.contributor.authorMikesell, Logan D.
dc.contributor.authorLivinghouse, Tom
dc.date.accessioned2023-09-15T18:56:18Z
dc.date.available2023-09-15T18:56:18Z
dc.date.issued2023-08
dc.descriptionThis document is the unedited Author’s version of a Submitted Work that was subsequently accepted for publication in The Journal of Organic Chemistry, copyright © American Chemical Society after peer review. To access the final edited and published work see https://doi.org/10.1021/acs.joc.3c00155en_US
dc.description.abstractA rapid and highly practical one-flask procedure for the positionally selective preparation of (acyloxy)methyl N-(2-hydroxybenzyl)iminodiacetate and related diesters from iminodiacetic acid and phenols is described. The key to this multicomponent phenol-Mannich condensation resides in the use of cesium iminodiacetate as the reaction partner. This protocol has been applied in an unusually direct synthesis of the intracellular fluorescent dye Calcein blue AM, for which scant experimental and spectroscopic data are presently available.en_US
dc.identifier.citationLogan D. Mikesell and Tom Livinghouse The Journal of Organic Chemistry 2023 88 (16), 12064-12068 DOI: 10.1021/acs.joc.3c00155en_US
dc.identifier.issn0022-3263
dc.identifier.urihttps://scholarworks.montana.edu/handle/1/18105
dc.language.isoen_USen_US
dc.publisherAmerican Chemical Societyen_US
dc.rightscopyright American Chemical Society 2023en_US
dc.rights.urihttp://web.archive.org/web/20190502075603/http://pubs.acs.org/paragonplus/copyright/jpa_form_a.pdfen_US
dc.subjectbase-catalyzeden_US
dc.subjectcesium iminodiacetateen_US
dc.subjectcalcien blue AMen_US
dc.subjectacyloxymethyl estersen_US
dc.titleBase-Catalyzed Phenol-Mannich Condensation of Preformed Cesium Iminodiacetate. The Direct Synthesis of Calcein Blue AM and Related Acyloxymethyl Estersen_US
dc.typeArticleen_US
mus.citation.extentfirstpage1en_US
mus.citation.extentlastpage5en_US
mus.citation.issue16en_US
mus.citation.journaltitleThe Journal of Organic Chemistryen_US
mus.citation.volume88en_US
mus.identifier.doi10.1021/acs.joc.3c00155en_US
mus.relation.collegeCollege of Letters & Scienceen_US
mus.relation.departmentChemistry & Biochemistry.en_US
mus.relation.universityMontana State University - Bozemanen_US

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