Synthesis and chemical transformations of 1,5‐benzothiazepines

Lévai, Albert

doi:10.1002/jhet.5570370201

Cited by 62 publications

(29 citation statements)

References 98 publications

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“…However, only two papers 15,16) have been published to date on the synthesis of seven-membered tellurazepine rings. 1,4-Dibenzo[b,f]tellurazepine (7) 15) was prepared by the thermolysis of 9-azidoxanthene (6) in 1987. The one-pot synthesis of the 2-aryl-1,5-benzotellurazepines (9) 16) has been reported based on the condensation of sodium 2-aminophenyltellurolate (8) with arylpropargyl aldehydes.…”

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confidence: 99%

Studies on Tellurium-Containing Heterocycles. Part 22. Tellurazepine Ring System: Preparation of 1,5-Benzotellurazepin-4-ones and Their Conversion into Fully Unsaturated 1,5-Benzotellurazepines

Sashida

Satoh

2004

CHEMICAL & PHARMACEUTICAL BULLETIN

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The chemistry of the thiazepine ring systems, seven-membered heterocycles containing atoms of both sulfur and nitrogen has been reviewed.2-6) Monocyclic 1,4-thiazepine compounds (1, 2) have been prepared by the Schmidt ring-expansion of 4H-thiopyran-1,1-dioxides 7) and by the Beckmann rearrangement of thiapyran-4-one oxime.8) The syntheses of its benzo derivatives, the 1,5-benzothiazepines (3), were described by Hofmann and Fischer 9,10) and by Kaupp et al. 11)The procedure for the preparation of these compounds is the cis-addition of o-mercaptoaniline to propiolic acid, followed by the cyclization of the adducts. 1,4-Benzothiazepines (4) 12) have also been produced by the condensation of 2-mercaptobenzamide and bromoacetaldehyde diethylacetal. Furthermore, the photocycloaddition of 2-phenylbenzothiazole with acetylenes gave the 1,5-benzothiazepines (5) 13) in one step. In addition, a number of tellurium-nitrogen-containing heterocycles 14) have been prepared. However, only two papers 15,16) have been published to date on the synthesis of seven-membered tellurazepine rings. 1,4-Dibenzo[b,f]tellurazepine (7) 15) was prepared by the thermolysis of 9-azidoxanthene (6) in 1987. The one-pot synthesis of the 2-aryl-1,5-benzotellurazepines (9) 16) has been reported based on the condensation of sodium 2-aminophenyltellurolate (8) with arylpropargyl aldehydes.In recent years, we have been investigating the syntheses of the 3-benzotellurepines 17) and 1-benzotellurepines, 18,19) novel fully unsaturated seven-membered heterocycles containing a tellurium atom. More recently, a convenient synthetic route for the preparation of tellurochromones, 20) sixmembered tellurium-containing carbonyl compounds, was also reported. Our synthetic strategy 21,22) for the preparation of these compounds is based on the intramolecular cyclization of the tellurol moieties to a triple bond. In this respect, we report herein the synthesis of the title compounds 23) as an extension of increasing interest in our methodology for preparing the tellurium-containing heterocycles.The first sub-goal is the preparation of the tellurazepinones (14). The preparation of 14 from o-iodobenzoic acid (10) is shown in Chart 3. o-Iodophenylisocyanate (11) was easily prepared from 10 via one-step according to the diphenylphospholic azide (DPPA) procedure reported by Shioiri and Yamada 24) in almost quantitative yield. The successful reaction of the isocyanate (11) with Grignard reagents was a result of the sp 2 -sp carbon-carbon bond formation to afford the oiodopropiolanilides (12), the key starting compounds for the synthesis of the tellurazepinones (14). Compound 11 reacted with one equivalent of an alkynylmagnesium bromide in tetrahydrofuran (THF) at 0°C to give the corresponding anilides (12) as the sole product in moderate to good yields. The telluration of the o-iodopropiolanilides (12) via the lithium compound, which was the method for the preparation of the 1-benzotellurepines, was unsuccessful. Therefore, we examined our original telluration method for t...

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Studies on Tellurium-Containing Heterocycles. Part 22. Tellurazepine Ring System: Preparation of 1,5-Benzotellurazepin-4-ones and Their Conversion into Fully Unsaturated 1,5-Benzotellurazepines

Sashida

Satoh

2004

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…62,63 One of their subclasses contains the 2,3-dihydro-1,5-benzothiazepin-4(5H)-ones among which there are compounds with antidepressant and antianginal activities. For this reason, their chemical tansformations including the oxidation of the sulfur atom have been extensively studied.…”

Section: Stereoselective Sulfoxidation Of Sulfides With Dimethyldioximentioning

confidence: 99%

Dioxirane Oxidation of Sulfur‐Containing Organic Compounds

Lévai

2004

ChemInform

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Dedicated to Professor Branko AbstractThis short review describes the utilization of dioxiranes as convenient and extremely efficient electrophilic oxidants for the selective oxidation of sulfur-containing organic compounds. Relevant examples are included to illustrate the chemoselective and stereoselective oxidations of substances with several sites of oxidation. Electrophilic character of the dioxiranes is shown via the oxidation of compounds with two sulfur heteroatoms.

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“…Three possible benzocondensed derivatives of 1,5-benzothiazepines viz. 1,4-, 4,1-and 1,5-benzothiazepines 19 are kwown. Benzothiazepines have their role in the treatment of muscle relaxant 20 , cardiovascular disorders 21 , as Ca 2+ channel blockers 22 and inhibitors of HIVintegrase 23 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Some Fluorinated 1, 5 - Benzothiazepines and Pyrazolines

Jagadhani¹,

Kundlikar²,

Karale³

2015

Orient. J. Chem

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ABSTRACT4-Bromo-2-fluorobenzaldehyde 1 when treated with substituted hydroxy acetophenones 2 yields chalcones 3. These chalcones were refluxed with 2-aminothiophenol gave "2-[2-(4-bromo-2-fluorophenyl)-2,3-dihydro-1,5-benzothiazepin-4-yl]phenol" 4 and when treated with hydrazine hydrate gave the compound "2- [5-(4-bromo-2-fluorophenyl)-4,5-dihydro-1H-pyrazol-3-yl]phenol" 5. The structures of compounds have been established on the basis of spectral data.

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Synthesis and chemical transformations of 1,5‐benzothiazepines

Cited by 62 publications

References 98 publications

Studies on Tellurium-Containing Heterocycles. Part 22. Tellurazepine Ring System: Preparation of 1,5-Benzotellurazepin-4-ones and Their Conversion into Fully Unsaturated 1,5-Benzotellurazepines

Studies on Tellurium-Containing Heterocycles. Part 22. Tellurazepine Ring System: Preparation of 1,5-Benzotellurazepin-4-ones and Their Conversion into Fully Unsaturated 1,5-Benzotellurazepines

Dioxirane Oxidation of Sulfur‐Containing Organic Compounds

Synthesis and Characterization of Some Fluorinated 1, 5 - Benzothiazepines and Pyrazolines

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