| 1. |
- Janosik, Tomasz, et al.
(author)
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Chemistry and Properties of Indolocarbazoles
- 2018
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In: Chemical Reviews. - : American Chemical Society (ACS). - 0009-2665 .- 1520-6890. ; 118:18, s. 9058-9128
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Journal article (peer-reviewed)abstract
- The indolocarbazoles are an important class of nitrogen heterocycles which has evolved significantly in recent years, with numerous studies focusing on their diverse biological effects, or targeting new materials with potential applications in organic electronics. This review aims at providing a broad survey of the chemistry and properties of indolocarbazoles from an interdisciplinary point of view, with particular emphasis on practical synthetic aspects, as well as certain topics which have not been previously accounted for in detail, such as the occurrence, formation, biological activities, and metabolism of indolo[3,2-b]carbazoles. The literature of the past decade forms the basis of the text, which is further supplemented with older key references.
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| 2. |
- Hasimbegovic, Vedran, et al.
(author)
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The synthesis of some 3-acylindoles revisited
- 2007
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In: Journal of Heterocyclic Chemistry. - : Wiley. - 0022-152X .- 1943-5193. ; 44:5, s. 1213-1217
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Journal article (peer-reviewed)abstract
- A study probing the scope of acylation of indoles with dicarboxylic acids in acetic anhydride has beenperformed, resulting in products incorporating 3-acylindole- or 1-acylindole motifs depending on thechoice of the acid reactant. Synthetically useful results were only obtained from reactions involvingmalonic acid or Meldrum’s acid. Correlations to previous studies have also been made and discussed.
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| 3. |
- Janosik, Tomasz, et al.
(author)
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Efficient sulfonation of 1-phenylsulfonyl-1H-pyrroles and 1-phenylsulfonyl-1H-indoles using chlorosulfonic acid in acetonitrile
- 2006
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In: Tetrahedron. - : Elsevier BV. - 0040-4020 .- 1464-5416. ; 62:8, s. 1699-1707
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Journal article (peer-reviewed)abstract
- The sulfonation of various 1-phenylsulfonyl-1H-pyrroles and 1-phenylsulfonyl-1H-indoles using chlorosulfonic acid in acetonitrile has been studied, leading to the development of a clean and operationally simple protocol allowing direct synthesis of the corresponding 1-phenylsulfonyl-1H-pyrrole-3-sulfonyl chlorides and 1-phenylsulfonyl-1H-indole-3-sulfonyl chlorides, respectively, both of which may be easily converted to various sulfonamide derivatives by treatment with nitrogen nucleophiles. Efficient and selective removal of the phenylsulfonyl- or tosyl groups in the sulfonamide series may be achieved under mild conditions.
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| 4. |
- Janosik, Tomasz, et al.
(author)
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Sulfur-rich heterocycles from 2-metalated benzo[b]thiophene and benzo[b]furan : Synthesis and structure
- 2002
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In: Journal of Organic Chemistry. - : American Chemical Society (ACS). - 0022-3263 .- 1520-6904. ; 67:17, s. 6220-6223
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Journal article (peer-reviewed)abstract
- The reaction of 2-lithiated benzo[b]thiophene with 8 equiv of elemental sulfur was found to give pentathiepino[6,7-b]benzo[d]thiophene. In contrast, treatment of 2-lithiated benzo[b]furan with sulfur under similar conditions produced the interesting ring system bis(benzo[4,5]-furo)[2,3-e:3',2'-g][1,2,3,4]tetrathiocine. Both of these new cyclic polysulfides were studied by X-ray crystallography. Two polymorphic forms of pentathiepino[6,7-b]benzo[d]thiophene were found, displaying similar conformations but different packing schemes, which was also evident from powder diffraction data.
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| 5. |
- Janosik, Tomasz, et al.
(author)
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Synthesis of the marine alkaloids rhopaladins A, B, C and D
- 2002
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In: Tetrahedron. - 0040-4020 .- 1464-5416. ; 58:14, s. 2813-2819
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Journal article (peer-reviewed)abstract
- The total synthesis of all four known rhopaladins, A-D, isolated from the Okinawan marine tunicate Rhopalaea sp., in two synthetic steps is described, involving an imidate based cyclization with tryptophan esters as the key step to afford the appropriately substituted imidazolinone unit. A short and efficient new synthesis of indol-3-yl-carbonyl nitriles from indol-3-yl-carboxaldehydes and trimethylsilyl cyanide, followed by oxidation with DDQ is also described.
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| 6. |
- Janosik, Tomasz, et al.
(author)
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Thionation of bisindole derivatives with P4S10 or elemental sulfur
- 2002
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In: Journal of the Chemical Society - Perkin Transactions 1. - : Royal Society of Chemistry (RSC). - 1472-7781 .- 1364-5463. ; :3, s. 330-334
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Journal article (peer-reviewed)abstract
- Thionation reactions of several bisindole derivatives using elemental sulfur or P4S10 in pyridine have been studied, leading to formation of several novel structures. The reaction of indigo or isatin with P4S10 gave the structurally new salt 10, which could be transformed into the ethyl derivative 11. The first example of a thionated indigo derivative, monothioindigo (6), was isolated in low yield from the thionation of isatin. Treatment of 3,3'-biindolyl with sulfur in hot DMF produced the previously known tetrasulfide 1, which was studied by X-ray crystallography, thus also establishing that 1 is chiral in the crystalline state. The structure of an additional thionation product, the thienoindole derivative 34 was also solved using X-ray crystallography.
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| 7. |
- Rewcastle, G W, et al.
(author)
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Reactions of 2-lithiated indoles with elemental sulfur. Formation of pentathiepino[6,7-b]indoles and indoline-2-thiones
- 2001
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In: Tetrahedron. - 0040-4020 .- 1464-5416. ; 57:33, s. 7185-7189
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Journal article (peer-reviewed)abstract
- The reactions of 2-lithiated indole and 1-methylindole with elemental sulfur have been studied, leading e.g. to a rational approach to pentathiepino[6,7-b]indoles 5 and 10. Notable amounts of the previously known tetrathiocino[5,6-b:8,7-b ' ]diindole 11 could be observed as a side reaction in the preparation of 10. Treatment of the anions of indoline-2-thiones 6 or 7 with sulfur also gave the pentathiepins 5 or 10, respectively. In addition, a convenient and clean lithiation route to indoline-2-thione (6) has been developed.
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| 8. |
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| 9. |
- Wahlström, Niklas, et al.
(author)
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Synthetic Applications of Cyanoacetylated Bisindoles : Synthesis of Novel Cycloheptadiindoles, Indolocarbazoles, and Related Aza Analogues.
- 2007
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In: Journal of Organic Chemistry. - : American Chemical Society (ACS). - 0022-3263 .- 1520-6904. ; 72:15, s. 5886-5889
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Journal article (peer-reviewed)abstract
- (Chemical Equation Presented) Cyclization reactions involving cyanoacetylated bisindoles have been studied, providing access to various novel cyclohepta[2,1-b:3,4-b′]diindole derivatives as well as some related fused pentacyclic systems. Treatment of 3-cyanoacetyl-2,3′-diindolylmethane with methanesulfonic acid gave 6-(cyanomethyl)indolo[3,2-b]carbazole in a good yield.
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| 10. |
- Andersson, Maria, et al.
(author)
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Synthesis and bioanalytical evaluation of morphine-3-O-sulfate and morphine-6-O-sulfate in human urine and plasma using LC-MS/MS
- 2012
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In: Journal of Separation Science. - : Wiley. - 1615-9306 .- 1615-9314. ; 35:3, s. 367-375
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Journal article (peer-reviewed)abstract
- The aim of this work was to synthesize morphine-3-O-sulfate and morphine-6-O-sulfate for use as reference substances, and to determine the sulfate conjugates as possible heroin and morphine metabolites in plasma and urine by a validated LC-MS/MS method. Morphine-6-O-sulfate and morphine-3-O-sulfate were prepared as dihydrates from morphine hydrochloride, in overall yields of 41 and 39% with product purities of >99.5% and >98%, respectively. For bioanalysis, the chromatographic system consisted of a reversed-phase column and gradient elution. The tandem mass spectrometer was operated in the positive electrospray mode using selected reaction monitoring, of transition m/z 366.15 to 286.40. The measuring range was 5500?ng/mL for morphine-3-O-sulfate and 4.5454?ng/mL for morphine-6-O-sulfate in plasma. In urine, the measuring range was 505000?ng/mL for morphine-3-O-sulfate and 45.44544?ng/mL for morphine-6-O-sulfate. The intra-assay and total imprecision (coefficient of variation) was below 11% for both analytes in urine and plasma. Quantifiable levels of morphine-3-O-sulfate in authentic urine and plasma samples were found. Only one authentic urine sample contained a detectable level of morphine-6-O-sulfate, while no detectable morphine-6-O-sulfate was found in plasma samples.
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