Synthesis and molecular crystal of 3-Chloro-2-(1-chloro-1-methyl-ethyl)-2,3-dihydro-1H-naphtho[2,1-b]oxepin-4-one (original) (raw)
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An Unusual Synthesis of N-Unsubstituted Benzazepinones
Organic Letters, 2012
A short route to novel bicyclic N-unprotected benzazepinones is described starting from N-acetoxyanilides involving radical addition and cyclization with concomitant homolytic rupture of the NÀO bond. We describe here an unexpected route to N-unsubstituted benzazepinone we discovered while examining a radical-based approach to cyclic hydroxamic acids. The strong chelating ability of hydroxamic acids toward metal ions such as zinc has made them popular targets for medicinal chemists. Numerous members of this family have indeed been reported to be potent inhibitors of histone deacetylase and matrix metalloproteinases. 1 Other interesting biological properties include antibiotic, antifungal, anti-inflammatory and anticancer activities. 1,2 While most hydroxamic acids described are linear derivatives, such as the antibiotic fosmidomycin 1, a few cases where the hydroxamate motif is part of a ring appear to be particularly interesting (Figure 1). Examples include cobactin T, a siderophore growth promoter isolated from mycobacteria, 3 and PF-04859989, 3, an irreversible kynurenine aminotransferase II inhibitor developed by Pfizer for treating schizophrenia. 4
Medicinal Chemistry Research, 2021
Two new Schiff bases, N, N'-(1,3-phenylenebis(methanylylidene))bis(4-bromoaniline) (1) and N, N'-(1,3-phenylenebis (methanylylidene))bis(4-methoxyaniline) (2), have been synthesized by the reaction between isophthalaldehyde and appropriate aniline derivatives, and characterized by physico-chemical and spectroscopic methods. The structures of new compound 1 and 2 have been characterized crystallographically. Moreover, structural optimization by DFT calculations have been performed and compared with the experimental data. The compounds were also screened for in vitro antibacterial activities against four human pathogenic bacteria and their minimum inhibitory concentrations showed moderate antibacterial activities.
Powder Diffraction, 2011
The 7-methyl-cis-2-(1’-naphthyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-ol (chemical formula C21H21NO) was prepared via the reductive cleavage of the bridged N-O bond of the corresponding 7-methyl-2-exo-(1′-naphthyl)-1,4-epoxytetrahydro-1-benzazepine. The X-ray powder diffraction pattern for the new compound was analyzed and found that the title compound crystallizes in a monoclinic system with space group P2/c (No. 13) and refined unit-cell parameters a = 11.012(2), b = 18.613(5), c = 7.316(4) Å, β = 102.88(3) ° and V = 1461.8(7) Å3.
Acta Crystallographica Section C Structural Chemistry, 2016
Tetrahydro-1-benzazepines have been described as potential antiparasitic drugs for the treatment of chagas disease and leishmaniasis, two of the most important so-called `forgotten tropical diseases' affecting South and Central America, caused byTrypanosoma cruziandLeishmania chagasiparasites, respectively. Continuing our extensive work describing the structural characteristics of some related compounds with interesting biological properties, the crystallographic features of three epoxy-1-benzazepines, namely (2SR,4RS)-6,8-dimethyl-2-(naphthalen-1-yl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, (1), (2SR,4RS)-6,9-dimethyl-2-(naphthalen-1-yl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, (2), and (2SR,4RS)-8,9-dimethyl-2-(naphthalen-1-yl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, (3), all C22H21NO, and two 1-benzazepin-4-ols, namely 7-fluoro-cis-2-[(E)-styryl]-2,3,4,5-tetrahydro-1H-1-benzazepin-4-ol, C18H18FNO, (4), and 7-fluoro-cis-2-[(E)-pent-1-enyl]-2,3,4,5-tetrahydro...
11.Use of 0002www.iiste.org Call_for_Paper-Ethoxy(4H)-3,1-benzoxazin-4-one as a Precursor
The interactions of 2-ethoxy(4H)-3,1-benzoxazin-4-one (1) with various nitrogen nucleophiles such as ammonium acetate, hydrazine hydrate, ethanolamine, p-phenylenediamine, o-phenylenediamine, otolidine, dapsone, 2-aminophenol, 4-aminophenol, 4-aminobenzoic acid and 2-aminonicotinic acid have been discussed. The reactions of 2-thoxy-(3H)-quinazolin-4-one with ethyl chloroformate, phosphorus pentasulfide, chloroacetyl chloride and phosphorus oxychloride have also been investigated. Similar reactions of 2-ethoxy-4-chloroquinazoline with hydrazine hydrate and thiosemicarbazide have been introduced. Aminolysis of the 2-ethoxy group in some of the thiadiazoloquinazolinone derivatives has been attempted. The interactions of these aminolized derivatives and the 3-aminoquinazolinone with chloroacetyl chloride have been studied. All of the synthesized derivatives have been used in a wide range as starting materials for the synthesis of novel quinazoline and/or quinazolinones which have biological activity. The structures of all these products, obtained by heterocyclic ring opening and ring closure, were inferred by the IR, MS, 1 H NMR spectral as well as elemental analyses.
Powder Diffraction, 2011
The 6,8-dimethyl-cis-2-vinyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-ol (2a) (Chemical formula C14H19NO) and 8-chloro-9-methyl-cis-2-(prop-1-en-2-yl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-ol (2b) (Chemical formula C14H18ClNO) were prepared via the reductive cleavage of the bridged N-O bond of the corresponding 1,4-epoxytetrahydro-1-benzazepines. The X-ray powder diffraction patterns for the new compounds were obtained. The compound 2a was found to crystallize in an orthorhombic system with space group Pmn21 (No. 31), refined unit-cell parameters a = 19.422(6) Å, b = 6.512(3) Å, c = 9.757(4) Å and V = 1234.0(5) Å3. The compound 2b was found to crystallize in a monoclinic system with space group P21/m (No. 11), refined unit-cell parameters a = 17.570(4) Å, b = 8.952(3) Å, c = 14.985(4) Å, β = 101.66(2)°, and V = 2308.3(9) Å3.
Zenodo (CERN European Organization for Nuclear Research), 1974
With a view to increasing our understanding of the conformation of catecholamines representing an 'ideal' tit of tbe molecules at the adrenergic receptor site, cisand trans-2.-hydroxy-, 3-hydroxy and 2., 3-dibydroxy-6amino-(and isopropylamino)-6, 7, 8, 9-tetrahydro-SH-benzocyclohepten-5-ols and some related compmmds, which incorporate a phenyl-ethanolamine residue, a-common denominator of many adrenergic compounds, in a rigid framework, have been synthesised and their biological activity studied. Some significant differences between the properties of 6-amino-6, 7, 8, 9-tetrahydro-5H-benzocyclohepten-5-ols and the corresponding aminotetralols, indanols and acyclic compounds are : (i) very facile acid catalysed epimerisation of both cis and trans-isomers (3N HC1 for 30 at 100°), and (ii) NO -acetyl migration taking place in both cis and trans-isomers with retention of configuration. Only in the case of 6, 7-trans-7-phenyl-6-amino-6, 7, 8, 9-tetrahydro-5H-benzocyclohepten-5-ols and 4-amino-2., 3, 4, 5-tetrahydro-1-benzoxepin-5-ols It has been found that only the trans-isomer undergoes epimerisation and gradually an increasing proportion of the cis-isomer accumulates in the reaction mixture. Stereochemical assignments and proposals for probable conformations are based on nmr studies. A twist chair conformation has been proposed for cisand trans-6-amino-6, 7, 8, 9-tetrahydro-5H-benzocyclohepten-5-ols, while for 6, 1-trans-S, 6-cis• and trans-7-phenyl-6, 7, 8, 9-tetrahydro-SH-benzocycloheptenols the nmr data can be best fitted for boat conformations. A characteristic feature of the nmr spectra of these compounds was the marked downfield shift of H-4, which is peri to tbe 5-0H group, in one of the isomers ; the OH group in this isomer has been assigned equatorial geometry. In a further study of the nature ofthis deshielding effect 5, 7-cisand tralls-7-phenyl-6, 7, ~. 9-tetrahydro-58-benzocyclohepten-5-ols and their corresponding 0-methyl and 0-acetyl derivatives have been synthesised and their nmr studied ; it has been found that tbe extent of deshielding is related to the availability of the lone pair of electrons on the oxygen. The formation of hydrogen bond between H-4 as donor and OR (R=H, Me, Ac) as acceptor may be involved. Both cisand trans-2., 3-dihydroxy-6-amino-6, 7, 8, 9-tetrahydro-benzocycloheptenols show typical 01-sympathomimetic activity. These fu1dings have been discussed in terms of tbe probable structural profile of 01 •adrenergic receptor.
HETEROCYCLES, 2010
Synthesis of four novel classes of structurally related fused hetero-pentacyclic compounds, naphtho[2,3-b]thieno[2,3-d][1]benzothiepins (Ia), naphtho[1,2-b]thieno[2,3-d][1]benzothiepins (IIa), naphtho[2,3-b]thieno-[2,3-d][1]benzoxepins (Ib,c) and naphtho[1,2-b]thieno[2,3-d][1]benzoxepins (IIb,c), is described. The key intermediates were the tetracyclic ketones,
Synthetic Study of Natural Metabolites Containing a Benzo[c]oxepine Skeleton: Heterocornol C and D
International Journal of Molecular Sciences
A versatile strategy for the enantioselective synthesis of a benzo[c]oxepine structural core containing natural secondary metabolites was developed. The key steps of the synthetic approach include ring-closing alkene metathesis for seven-member ring construction, the Suzuki–Miyaura cross-coupling reaction for the installation of the double bond and Katsuki–Sharpless asymmetric epoxidation for the introduction of chiral centers. The first total synthesis and absolute configuration assignment of heterocornol D (3a) were achieved. Four stereoisomers, 3a, ent-3a, 3b and ent-3b, of this natural polyketide were prepared, starting with 2,6-dihydroxy benzoic acid and divinyl carbinol. The absolute and relative configuration of heterocornol D was assigned via single-crystal X-ray analysis. The extension of the described synthetic approach is further presented with the synthesis of heterocornol C by applying the ether group reduction method to the lactone.