New Routes for the Synthesis Novel Heterocyclic via Formation of C-N Bond and via Cleavage a Thiazine Ring of 1,4-Benzothiazine

Fatima Al-Omran and Adel Abou El-Khair
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Adel Abou El-Khair: Department of Chemistry, Kuwait University, Kuwait

Organic & Medicinal Chemistry International Journal, 2016, vol. 1, issue 1, 36-46

Abstract: The reactions of 2-aminothiophenol with acetylacetone in refluxing DMSO or ethanol wasinvestigated. Treatment of 1 with enaminone 5 gave 1,4-benzothiazine derivative 6. A reasonable mechanism represented the formation of pyridone derivative 11 by treatment of 2 with malononitrile. Reactions of 2 with cyanoacetohydrazide, thiosemicarbazide,hydrazine hydrate and phenyl hydrazine afforded the compounds 13, 15 and, 17a-b respectively. Condensation of 13 with 4-methoxy benzaldehyde gave 18. The latter compound reacted with malononitrile gave pyridone derivative 19. A reasonable mechanism interpreted the formation of pyrazolo[3,4-b]pyridine derivative 20 from the reaction of 13 with DMF-DMA via cleavage of a thiazine ring of 1,4-benzothiazine. The structures of all newly synthesized compounds elucidated by elemental analysis 1H-NMR and 13C-NMR spectra, Ms and X-ray crystallographic investigations. The reported crystal structures of these novel 1,4-benzothiazine derivatives are expected to be a remarkable contribution to the crystallographic database of heterocyclic compounds.

Keywords: juniper publishers:Medicinal Chemistry; Biochemistry Journal; Pharmacology Journal; biochemical pharmacology; molecular pharmacology; biochemistry; open access journals; peer reviewed journals; Open Access; Journal of Molecular Biochemistry; International Research Journal of Pure and Applied Chemistry; World Journal of Biological Chemistry; Biochemistry and Analytical Biochemistry; Biochemistry & Physiology: Open Access; Molecular Biology International; Plant Biochemistry & Physiology; International Journal of Molecular Sciences; Journal of Clinical and Medical Genomics; Environmental Analytical Chemistry; Medicinal Chemistry; Juniper publishers reivews (search for similar items in EconPapers)
Date: 2016
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Persistent link: https://EconPapers.repec.org/RePEc:adp:jomcij:v:1:y:2016:i:1:p:36-46

DOI: 10.19080/OMCIJ.2016.01.555555

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