Davis-Beirut reaction: Route to thiazolo-, thiazino-, and thiazepino-2 h -indazoles

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dc.contributor.authorFarber, Kelli M.
dc.contributor.authorHaddadin, Makhluf J.
dc.contributor.authorKurth, Mark J.
dc.contributor.departmentDepartment of Chemistry
dc.contributor.facultyFaculty of Arts and Sciences (FAS)
dc.contributor.institutionAmerican University of Beirut
dc.date.accessioned2025-01-24T11:21:41Z
dc.date.available2025-01-24T11:21:41Z
dc.date.issued2014
dc.description.abstractMethods for the construction of thiazolo-, thiazino-, and thiazepino-2H-indazoles from o-nitrobenzaldehydes or o-nitrobenzyl bromides and S-trityl-protected 1°-aminothioalkanes are reported. The process consists of formation of the requisite N-(2-nitrobenzyl)(tritylthio)alkylamine, subsequent deprotection of the trityl moiety with TFA, and immediate treatment with aq. KOH in methanol under Davis-Beirut reaction conditions to deliver the target thiazolo-, thiazino-, or thiazepino-2H-indazole in good overall yield. Subsequent S-oxidation gives the corresponding sulfone. © 2014 American Chemical Society.
dc.identifier.doihttps://doi.org/10.1021/jo501014e
dc.identifier.eid2-s2.0-84905398375
dc.identifier.pmid25019525
dc.identifier.urihttp://hdl.handle.net/10938/25270
dc.language.isoen
dc.publisherAmerican Chemical Society
dc.relation.ispartofJournal of Organic Chemistry
dc.sourceScopus
dc.subjectBenzaldehydes
dc.subjectBenzyl compounds
dc.subjectIndazoles
dc.subjectMolecular structure
dc.subjectOxidation-reduction
dc.subjectThiazines
dc.subjectThiazoles
dc.subjectChemistry
dc.subjectOrganic compounds
dc.subject10 chloro 3,4 dihydro 2h [1,3]thiazino[3,2 b]indazole
dc.subject2 (1 hydroxypropan 2 yl)isoindoline 1,3 dione
dc.subject2 (1 iodopropan 2 yl)isoindoline 1,3 dione
dc.subject2 [1 (tritylthio)propan 2 yl]isoindoline 1,3 dione
dc.subject2,3 dihydrothiazolo[3',2':1,5]pyrazolo[4,3 b]pyridine
dc.subject2,3 dihydrothiazolo[3,2 b]indazole
dc.subject2,3 dihydrothiazolo[3,2 b]indazole 1,1 dioxide
dc.subject2,3,4,5 tetrahydro [1,3]oxazepino[3,2 b]indazole
dc.subject2,3,4,5 tetrahydro [1,3]thiazepino[3,2 b]indazole
dc.subject2,3,4,5 tetrahydro [1,3]thiazepino[3,2 b]indazole 1,1 dioxide
dc.subject3 methyl 1 (tritylthio)butan 2 amine
dc.subject3 methyl 2,3 dihydrothiazolo[3,2 b]indazole
dc.subject3,4 dihydro 2h pyrido[3',2':3,4]pyrazolo[5,1 b][1,3]thiazine
dc.subject3,4 dihydro 2h [1,3]thiazino[3,2 b]indazole
dc.subject3,4 dihydro 2h [1,3]thiazino[3,2 b]indazole 8 carboxylic acid
dc.subject3,4 dihydro-2 h [1,3]thiazino[3,2 b]indazole 1,1 dioxide
dc.subject7,8 dihydro [1,3]dioxolo[4,5 f ]thiazolo[3,2 b]indazole
dc.subject7,8 dihydro [1,3]dioxolo[4,5 f ]thiazolo[3,2 b]indazole 9,9 dioxide
dc.subject7,8,9,10 tetrahydro [1,3]dioxolo[4,5 f][1,3]thiazepino[3,2 b]indazole
dc.subject8,9 dihydro 7h [1,3]dioxolo[4,5 f ][1,3]thiazino[3,2 b] indazole 10,10 dioxide
dc.subject8,9 dihydro 7h [1,3]dioxolo[4,5 f ][1,3]thiazino[3,2 b]indazole
dc.subject8,9 dimethoxy 3,4 dihydro 2h [1,3]thiazino[3,2 b]indazole
dc.subject9 bromo 3,4 dihydro 2h [1,3]thiazino[3,2 b]indazole
dc.subjectBenzaldehyde derivative
dc.subjectBenzo[4,5]thiazolo[3,2 b]indazole
dc.subjectBromine derivative
dc.subjectIndazole derivative
dc.subjectMercaptamine
dc.subjectSulfone
dc.subjectUnclassified drug
dc.subjectUnindexed drug
dc.subjectBenzyl derivative
dc.subjectThiazine derivative
dc.subjectThiazole derivative
dc.subject2-nitrobenzyl
dc.subjectAlkylamine
dc.subjectDeprotection
dc.subjectIndazole
dc.subjectNitrobenzyl bromides
dc.subjectReaction conditions
dc.subjectAmination
dc.subjectArticle
dc.subjectChemical reaction
dc.subjectDavis beirut reaction
dc.subjectElectrophilicity
dc.subjectLiquid chromatography
dc.subjectMass spectrometry
dc.subjectOxidation
dc.subjectReaction time
dc.subjectStereospecificity
dc.subjectChemical structure
dc.subjectOxidation reduction reaction
dc.subjectSynthesis
dc.subjectPotassium hydroxide
dc.titleDavis-Beirut reaction: Route to thiazolo-, thiazino-, and thiazepino-2 h -indazoles
dc.typeArticle

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