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Analogues of the Cyclic Hydroxamic Acid 2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3-one: Decomposition to Benzoxazolinones and Reaction with β-Mercaptoethanol

Authordc.contributor.authorAtkinson, Jeffrey 
Authordc.contributor.authorMorand, Peter 
Authordc.contributor.authorArnason, John T. 
Authordc.contributor.authorNiemeyer, Hermann M. 
Authordc.contributor.authorBravo, Héctor R. 
Admission datedc.date.accessioned2018-12-20T14:34:15Z
Available datedc.date.available2018-12-20T14:34:15Z
Publication datedc.date.issued1991
Cita de ítemdc.identifier.citationJournal of Organic Chemistry, Volumen 56, Issue 5, 2018, Pages 1788-1800
Identifierdc.identifier.issn15206904
Identifierdc.identifier.issn00223263
Identifierdc.identifier.other10.1021/jo00005a025
Identifierdc.identifier.urihttp://repositorio.uchile.cl/handle/2250/156474
Abstractdc.description.abstractAnalogues of the aglucones of naturally occurring cyclic hydroxamic acids (2,4-dihydroxy-1,4-benzoxazin-3-ones) from Gramineae (Poaceae) have been synthesized by the reductive cyclization of the ring-substituted methyl α-(o-nitrophenoxy)-α-methoxyacetates, followed by demethylation of the C-2 methoxy group with BBr3 or BCl3 to reveal the 2-hydroxy group. A structure-activity series was produced by varying the substituent at C-7 on the aromatic ring [R = MeO (1), t-Bu (6), Me (7), H (8), Cl (9), F (10), C02Me (11a)]. The pKa, values for the hydroxamic acid and the phenol moieties were determined for each member of the C-7 series. They correlated well with σ in a linear free energy relationship (LFER) yielding values of p = 0.71 (with σp) for pKa1 (the hydroxamic acid) and ρ = 1.6 (with σm) for pKa2 (the phenol). A LFER also existed between the rate constants for the unimolecular decomposition of these hydroxamic acids to benzoxazolinones and σ+ (ρ=-1.1). The rates of hydroxamic acid red
Lenguagedc.language.isoen
Type of licensedc.rightsAttribution-NonCommercial-NoDerivs 3.0 Chile
Link to Licensedc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/3.0/cl/
Sourcedc.sourceJournal of Organic Chemistry
Keywordsdc.subjectOrganic Chemistry
Títulodc.titleAnalogues of the Cyclic Hydroxamic Acid 2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3-one: Decomposition to Benzoxazolinones and Reaction with β-Mercaptoethanol
Document typedc.typeArtículo de revista
Catalogueruchile.catalogadorSCOPUS
Indexationuchile.indexArtículo de publicación SCOPUS
uchile.cosechauchile.cosechaSI


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Except where otherwise noted, this item's license is described as Attribution-NonCommercial-NoDerivs 3.0 Chile