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Study of the reaction of chalcone analogs of dehydroacetic acid and o-aminothiophenol: Synthesis and structure of 1,5-benzothiazepines and 1,4-benzothiazines

AuthorsPrakash, O.; Kumar, A.; Sadana, A.; Prakash, R.; Singh, S. P.; Claramunt, Rosa M.; Sanz, D.; Alkorta, Ibon ; Elguero, José
Issue Date2005
PublisherPergamon Press
CitationTetrahedron 61: 6642- 6651 (2005)
AbstractTreatment of α,β-unsaturated carbonyl compounds, obtained by the reaction of DHA and aromatic (or heteroaromatic) aldehydes, with o-aminothiophenol results in the formation of 1,5-benzothiazepines and/or 1,4-benzothiazines depending upon the reaction conditions and structure of the aldehydes. The products were characterized by the combined use of multinuclear 1D and 2D NMR and GIAO/DFT calculations of 1H, 13C and 15N chemical shifts. The tautomerism of these compounds in solution was determined, they have an exocyclic CC double bond.
Identifiersdoi: 10.1016/j.tet.2005.03.035
issn: 0040-4020
Appears in Collections:(IQM) Artículos
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