Novel Syntheses of 2,3-Dihydro-1,5-benzothiazepin-4(5H)-ones and 2H-1,4-Benzothiazin-3(4H)-ones

Katritzky, Alan R.; Odens, Herman H.; Zhang, Suoming; Rostek, Charles J.; Maender, Otto W.

doi:10.1021/jo0101959

Cited by 24 publications

(12 citation statements)

References 26 publications

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“…Intermediate compounds 323a-c, were isolated (but characterized only by 1 H NMR) and further used in the final cyclization step to obtain the target benzothiazepines 322a-c. Treatment of the intermediates 323a-c with DCC and subsequent purification by flash column chromatography gave the desired benzothiazepines 322a-c in 81-97% yields [75] (Scheme 58).…”

Section: Cyclization Of 3-{5-[anilino-2-(alkylamino)phenyl]sulfanyl}-mentioning

confidence: 99%

Benzo[1,5]thiazepine: Synthesis, Reactions, Spectroscopy, and Applications

El‐Bayouki

2013

Organic Chemistry International

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Section: Cyclization Of 3-{5-[anilino-2-(alkylamino)phenyl]sulfanyl}-mentioning

confidence: 99%

Benzo[1,5]thiazepine: Synthesis, Reactions, Spectroscopy, and Applications

El‐Bayouki

2013

Organic Chemistry International

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“…Tipical Procedure [16]. A mixture of the chalcones (2.5 mmol), 2-aminothiophenol (0.5 g, 4 mmol), AcOH (0.5 mL), HCl conc.…”

Section: Chemistrymentioning

confidence: 99%

“Anti-Michael” and Michael Additions in the Reactions of 2-Arylmethyliden-1,3-Indandiones with 2-Aminothiophenol

García¹,

Hernández-Suzan²,

Martínez-Klimova³

et al. 2017

IJOC

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A novel 2-indano[2,3b]-2-ferrocenyl-and 2-indano[2,3b]-2-(p-methoxyphenyl) [1,5]benzo-2,5-dihydrothiazepine 5a,b (addition Michael/cyclization) (~30.32%), indano[2,3b]-2-ferrocenyl-and 2-(p-methoxyphenyl) [1,4] benzothiazine 4a,b (addition "anti-Michael"/cyclization) (~45.43%), respectively, were obtained by the condensation of 2-ferrocenyl-and 2-(p-methoxyphenyl)methyliden-1,3-indandiones 1a,b with o-aminothiophenol 2 in the presence of AcOH and HCl. A new "anti-Michael" addition reaction of 1,4-bis-heteronucleophile 2 into 2-arylmethyliden-1,3-indandiones was reported.As a result of this reaction the product 1a,b was obtained. The structures of the resultant compounds were elucidated by IR, 1 H and 13 C NMR spectroscopy, mass spectrometry, elemental and X-ray diffraction analysis. The in vitro antitumor activity of the obtained products was researched using the following human cancer cell lines: glioblastoma (CNS U-251), prostatic adenocarcinoma (PC-3), chronic myelogenous leukemia (K562), colorectal adenocarcinoma (HCT-15), mammary adenocarcinoma (MCF-7), and small cell lung cancer (SKLU) and the sulforhodamine B (SRB) method. Among these new compounds some thiazine and thiazepine derivatives showed compelling in vitro antitumor effects on cell lines K-562, HCT-15, SKLU-1 and MCF-7.

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“…Endnoten dürfen nicht verwendet werden. Die Zitierung der Literatur erfolgt in Anlehnung an den "Vancouver style" [1] wie unten dargestellt (Bücher [2], Zeitschriften [3,4] …”

Section: Literaturunclassified

Instructions for Authors 2014 - Autorenhinweise 2014

2014

Sci. Pharm.

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Novel Syntheses of 2,3-Dihydro-1,5-benzothiazepin-4(5H)-ones and 2H-1,4-Benzothiazin-3(4H)-ones

Cited by 24 publications

References 26 publications

Benzo[1,5]thiazepine: Synthesis, Reactions, Spectroscopy, and Applications

Benzo[1,5]thiazepine: Synthesis, Reactions, Spectroscopy, and Applications

“Anti-Michael” and Michael Additions in the Reactions of 2-Arylmethyliden-1,3-Indandiones with 2-Aminothiophenol

Instructions for Authors 2014 - Autorenhinweise 2014

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