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  • 1.
    Bergman, Jan
    et al.
    Södertörn University, Avdelning Naturvetenskap. Karolinska Institute.
    Engqvist, Robert
    Karolinska Institute.
    Stålhandske, C
    Chemical Centre, Lund.
    Wallberg, H
    KTH.
    Studies of the reactions between indole-2,3-diones (isatins) and 2-aminobenzylamine2003In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 59, no 7, p. 1033-1048Article in journal (Refereed)
  • 2.
    Bergman, Jan
    et al.
    Södertörn University, Avdelning Naturvetenskap.
    Janosik, T
    Yudina, L
    Desarbre, E
    Lidgren, G
    Venemalm, L
    Reactions of 1,2-bis(1H-indol-2-yl)ethane: Formation of indolo[2,3-c]carbazole and cyclohept[1,2-b : 5,4-b ']bisindole derivatives2000In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 56, no 13, p. 1911-1916Article in journal (Refereed)
    Abstract [en]

    1,2-Bis(1H-indol-2-yl)ethane (9) has been prepared and converted into indolo[2,3-c]carbazole (8) using palladium acetate in refluxing acetic acid. Reaction of 9 with CoF3 in hot TFA led to isolation of cyclohept[1,2-b:5,4-b']bisindole derivatives 11 and 12, which could be elaborated into further derivatives. Treatment of 9 with orthoesters, aldehydes and ketones under acidic conditions afforded additional bisindoles containing a seven-membered ring.

  • 3.
    Bergman, Jan
    et al.
    Södertörn University, Avdelning Naturvetenskap.
    Rehn, S
    Synthesis of 4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid ethyl ester and its isomer 1-oxo-2,9-dihydro-1H-beta-carboline-4-carboxylic acid ethyl ester2002In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 58, no 45, p. 9179-9185Article in journal (Refereed)
    Abstract [en]

    4-Oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid ethyl ester was obtained when TosMIC was reacted with 3-methylene-oxindole acetic acid ethyl ester. An alternative synthesis to this pyrroloquinolone was performed via a reduction of a 2,3,4-trisubstituted pyrrole obtained in turn by treatment of a vinyl sulfone with ethyl isocyanoacetate under basic conditions. A beta-carboline, isomeric with the pyrroloquinolone, was synthesised utilizing a tosylimine.

  • 4.
    Bergman, Jan
    et al.
    Södertörn University, Avdelning Naturvetenskap. Karolinska Institute.
    Wahlström, Niklas
    Södertörn University, Avdelning Naturvetenskap. Karolinska Institute.
    Yudina, L N
    Tholander, J
    Lidgren, G
    Synthesis of indolocarbazole quinones; potent aryl hydrocarbon receptor ligands2002In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 58, no 7, p. 1443-1452Article in journal (Refereed)
    Abstract [en]

    Syntheses of indolo[2,3-b]carbazole-6,12-dione and the isomeric indolo[3,2-b]carbazole-6,12-dione, an extremely efficient inducer of the aryl hydrocarbon (Ah) receptor are described. Initial oxidation of the parent indolo[3,2-b]carbazole followed by several different ring-closing strategies produced the latter compound. Entries into syntheses of unsymmetrical 6,12-disubstituted indolo[2,3-b]carbazoles are also described.

  • 5.
    Engqvist, Robert
    et al.
    Södertörn University, Avdelning Naturvetenskap. Karolinska Institutet.
    Bergman, Jan
    Södertörn University, Avdelning Naturvetenskap. Karolinska Institutet.
    Synthesis of benzothiopyrano[2,3-b]indol-11-one and benzopyrano[2,3-b]indol-11-one2003In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 59, no 48, p. 9649-9653Article in journal (Refereed)
    Abstract [en]

    The fused heterocycles benzothiopyrano[2,3-b]indol-11-one and benzopyrano[2,3-b]indol-11-one, have been prepared from methyl 3-indole carboxylate in two steps.

  • 6.
    Engqvist, Robert
    et al.
    Södertörn University, School of Chemistry, Biology, Geography and Environmental Science. Karolinska Institutet.
    Stensland, Birgitta
    AstraZeneca.
    Bergman, Jan
    Södertörn University, School of Chemistry, Biology, Geography and Environmental Science. Karolinska Institutet.
    Reduction of indolo[2,3-b]quinoxalines2005In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 61, no 18, p. 4495-4500Article in journal (Refereed)
    Abstract [en]

    Reduction of indolo[2,3-b]quinoxalines with zinc in the presence of an anhydride gave N,N-diacyl trapped 6,11-dihydroindolo[2,3-b]quinoxalines in 43-92% yields. When the reduction with zinc was performed in TFA/TFAA, an unexpected ring opened product was isolated in 49% yield. The structure of this product could be identified as 1,2-dihydro-1-trifluoroacetyl-3-[(2-trifluoroacetylamino)phenyl]quinoxal ine.

  • 7.
    Janosik, Tomasz
    et al.
    Södertörn University, Avdelning Naturvetenskap. Karolinska Institutet.
    Johnson, Ann-Louise
    Södertörn University, Avdelning Naturvetenskap. Karolinska Institutet.
    Bergman, Jan
    Södertörn University, Avdelning Naturvetenskap. Karolinska Institutet.
    Synthesis of the marine alkaloids rhopaladins A, B, C and D2002In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 58, no 14, p. 2813-2819Article in journal (Refereed)
    Abstract [en]

    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.

  • 8. Janosik, Tomasz
    et al.
    Shirani, Hamid
    Wahlström, Niklas
    Malky, Ilham
    Stensland, Birgitta
    Bergman, Jan
    Södertörn University, School of Life Sciences. Karolinska Institute.
    Efficient sulfonation of 1-phenylsulfonyl-1H-pyrroles and 1-phenylsulfonyl-1H-indoles using chlorosulfonic acid in acetonitrile2006In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 62, no 8, p. 1699-1707Article in journal (Refereed)
    Abstract [en]

    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.

  • 9. Johnson, Ann-Louise
    et al.
    Bergman, Jan
    Södertörn University, School of Life Sciences. Karolinska Institute.
    Synthetic approaches towards an indole alkaloid isolated from the marine sponge Halichondria melanodocia2006In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 62, no 47, p. 10815-10820Article in journal (Refereed)
    Abstract [en]

    The exocyclic analogue of the indole alkaloid isolated from the marine sponge Halichondria melanodocia has been prepared via olefination of a phosphonoester derived from 3-(2-bromoacyl)indole. The formation of an unexpected indolylazepine is also discussed.

  • 10.
    Johnson, Ann-Louise
    et al.
    Södertörn University, School of Chemistry, Biology, Geography and Environmental Science. Karolinska Institute.
    Bergman, Jan
    Södertörn University, School of Chemistry, Biology, Geography and Environmental Science. Karolinska Institute.
    Sjögren, M
    Bohlin, L
    Synthesis of barettin2004In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 60, no 4, p. 961-965Article in journal (Refereed)
    Abstract [en]

    The indole alkaloid barettin (with bromine in 6-position), isolated from the marine sponge Geodia Barretti, has been synthesised via a Horner-Wadsworth-Emmons type reaction from 6-bromoindole-3-carboxaldehyde to introduce the dehydro-functionality. Subsequent deprotection and cyclisation afforded the natural product in Z-conformation.

  • 11. Rehn, Stanley
    et al.
    Bergman, Jan
    Södertörn University, School of Life Sciences. Karolinska Institute.
    The reaction between 3-aminocrotonates and oxindole-3-ylidene derivatives: synthesis of highly substituted pyrroles2005In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 61, no 12, p. 3115-3123Article in journal (Refereed)
    Abstract [en]

    The reaction between 3-aminocrotonates and 3-acetonylideneoxindole in refluxing toluene resulted in 2-pyrrolo-3 '-yloxindoles in high yields (around 90%). At room temperature the 2-pyrrolo-3 '-yioxindoles exists as keto-enol tautomers. Treatment with POCl3 yielded the 2-chloro-3-pyrrolyl indole, which gave the pyrrolo annulated indolopyran-2-one upon basic hydrolysis of 2-chloro-3-pyrrolyl indole methyl ester.

  • 12. Rewcastle, G W
    et al.
    Janosik, Tomasz
    Södertörn University, Avdelning Naturvetenskap. Karolinska Institute.
    Bergman, Jan
    Södertörn University, Avdelning Naturvetenskap. Karolinska Institute.
    Reactions of 2-lithiated indoles with elemental sulfur. Formation of pentathiepino[6,7-b]indoles and indoline-2-thiones2001In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 57, no 33, p. 7185-7189Article in journal (Refereed)
    Abstract [en]

    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.

  • 13.
    Slätt, Johnny
    et al.
    Södertörn University, Avdelning Naturvetenskap. Karolinska Institutet.
    Bergman, Jan
    Södertörn University, Avdelning Naturvetenskap. Karolinska Institutet.
    Oxygenation of 2,3-dihydroindoles2002In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 58, no 45, p. 9187-9191Article in journal (Refereed)
    Abstract [en]

    Isatogens (3-oxo-3H-indole 1-oxides) possess interesting biological properties and development of a general method to construct these derivatives has now been developed. Indolines (2,3-dihydroindoles) and isatogens have been prepared in an efficient route starting from indoles substituted in position 2. Reduction of the 2-substituted indoles was performed with tin and hydrochloric acid to give racemic indolines, which were converted to isatogens by 3-chloroperoxybenzoic acid (m-CPBA).

  • 14.
    Wahlström, Niklas
    et al.
    Södertörn University, School of Chemistry, Biology, Geography and Environmental Science. Karolinska Institute.
    Stensland, B
    Bergman, Jan
    Södertörn University, School of Chemistry, Biology, Geography and Environmental Science. Karolinska Institute.
    Synthesis of the marine alkaloid caulersin2004In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 60, no 9, p. 2147-2153Article in journal (Refereed)
    Abstract [en]

    A three-step synthesis of caulersin (3) from indole-2-acetic acid methyl ester and indole-2-carbonyl chloride is described. As the spectral data of the synthetic sample differed from those reported for the natural product, the structure was determined by X-ray crystallography.

  • 15. Witt, A
    et al.
    Bergman, Jan
    Södertörn University, Avdelning Naturvetenskap.
    Synthesis and reactions of some 2-vinyl-3H-quinazolin-4-ones2000In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 56, no 37, p. 7245-7253Article in journal (Refereed)
    Abstract [en]

    A simple, high-yielding synthesis of 2-vinyl-3H-quinazolin-4-one, 2-(1-chlorovinyl)-3H-quinazolin-4-one and 2-(1-bromovinyl)-3H-quinazolin-4-one. The 2-vinylquinazolinones 11a and 14 participate readily in nucleophilic addition reactions. Treatment with both carbon and nitrogen nucleophiles results in a clean conversion into a variety of 2-substituted 3H-quinazolin-4-one derivatives. The 2-(1-halovinyl)-3H-quinazolin-4-ones 11b and Ile reacted with carbon nucleophiles to give several derivatives of 2-substituted 3H-quinazolin-4-one, such as dihydrofurancarboxylic ethyl ester 23.

  • 16. Yudina, Larisa N
    et al.
    Bergman, Jan
    Södertörn University, Avdelning Naturvetenskap. Karolinska Institute.
    Synthesis and alkylation of indolo[3,2-b]carbazoles2003In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 59, no 8, p. 1265-1275Article in journal (Refereed)
1 - 16 of 16
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