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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 |
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| Authors: | Om Prakash,Ajay Kumar,Richa Prakash,Rosa M. Claramunt,Ibon Alkorta,José Elguero |
| Affiliation: | a Department of Chemistry, Kurukshetra University, Kurukshetra 136 119, India b Departamento de Química Orgánica y Bio-Orgánica, Facultad de Ciencias, UNED, Senda del Rey 9, E-28040 Madrid, Spain c Instituto de Química Médica, Centro de Química Orgánica ‘Manuel Lora-Tamayo’, CSIC, Juan de la Cierva, 3, E-28006 Madrid, Spain |
| Abstract: | Treatment 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. |
| Keywords: | 1,5-Benzothiazepines 1,4-Benzothiazines Tautomerism DFT-calculations GIAO chemical shifts |
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