| 1. |
- Bergman, Jan, et al.
(författare)
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Studies of the reactions between indole-2,3-diones (isatins) and 2-aminobenzylamine
- 2003
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Ingår i: Tetrahedron. - 0040-4020 .- 1464-5416. ; 59:7, s. 1033-1048
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Tidskriftsartikel (refereegranskat)abstract
- Reflux of equimolecular amounts 2-aminobenzylamine and isatins in acetic acid produced indolo[3,2-c]quinolin-6-ones in good yields. A proposed mechanism involving initial formation of a spiro compound is given. This isolable intermediate subsequently rearranges via a sequential isocyanate ring opening and a cyclisation process to a urea derivative which finally cyclized to the indolo[3,2-c]quinolin-6-ones. The urea derivative could be prepared separately and cyclized selectively to indolo[3,2-c]quinolin-6-one. Reaction of N-acetylisatin with 2-aminobenzylamine at room temperature yielded the 1,4-benzodiazepinone 3-(2-acetamidophenyl)-1,5-dihydro-1,4-benzodiazepin-2one whereas its isomer 2(2-acetamidophenyl)-4,5-dihydro-1,4-benzodiazepin-3-one was obtained from 2-(2-acetylaminophenyl)-N-(2-aminobenzyl)-2-oxoacetamide in acetic acid at room temperature. The previously unknown linear isomer of indolo[3,2-c]quinolin-6-one, i.e. indolo[2,3-blquinolin-11-one, has been prepared by thermal (260degreesC) cyclization of methyl 2-phenylamino indole-3-carboxylate, which in turn was prepared in two steps from methyl indole-3-carboxyl ate. (C) 2003 Elsevier Science Ltd. All rights reserved.
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| 2. |
- Johnson, Ann-Louise, et al.
(författare)
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Synthesis of barettin
- 2004
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Ingår i: Tetrahedron. - : Elsevier BV. - 0040-4020 .- 1464-5416. ; 60:4, s. 961-965
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Tidskriftsartikel (refereegranskat)abstract
- 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.
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| 3. |
- Slätt, Johnny, 1976-, et al.
(författare)
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Oxygenation of 2,3-dihydroindoles.
- 2002
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Ingår i: Tetrahedron. - 0040-4020 .- 1464-5416. ; 58:45, s. 9187-9191
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Tidskriftsartikel (refereegranskat)abstract
- Indolines (2,3-dihydroindoles) and isatogens (3-oxo-3H-indole 1-oxides) have been prepd. in an efficient route starting from indoles substituted in position 2. Redn. 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). [on SciFinder(R)]
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| 4. |
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| 5. |
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| 6. |
- Bergman, Jan, et al.
(författare)
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Acid-induced dimerization of 3-(1H-indol-3-yl)maleimides. Formation of cyclopentindole derivatives
- 2000
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Ingår i: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1. - : Royal Society of Chemistry (RSC). - 1470-4358 .- 1364-5463 .- 1472-7781. ; :16, s. 2615-2621
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Tidskriftsartikel (refereegranskat)abstract
- Acid-induced dimerizations of 3-substituted maleimides have been investigated, leading to e.g. the cyclopentindole 9 and the deeply coloured spiro compounds 24 and 25 in good yields. 3-(1H-Indol-3-yl)maleimide 6b readily gave the cycloaddition products 13-15 on treatment with appropriate dienophiles. In addition, several related 3,3-di-(1H-indol-3-yl)succinimides have been prepared and studied.
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| 7. |
- Bergman, Jan, et al.
(författare)
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Coupling reactions of indole-3-acetic acid derivatives. Synthesis of arcyriaflavin A
- 2000
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Ingår i: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1. - : Royal Society of Chemistry (RSC). - 1470-4358 .- 1364-5463 .- 1472-7781. ; :16, s. 2609-2614
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Tidskriftsartikel (refereegranskat)abstract
- The bisindolesuccinic acid methyl ester 10 was obtained by an iodine-promoted coupling of the dianion 9. The diester was converted to the N-benzylimide 12, which was oxidatively cyclized to the indolo[2,3-a]pyrrolo[3,4-c]carbazole 15. The diester 10 could be directly transformed to the known indolocarbazole diester 27 via acid-induced intramolecular cyclization in TFA. The same methodology gave arcyriaflavin A 4 from the succinimide 18b.
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| 8. |
- Bergman, Jan, et al.
(författare)
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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 derivatives
- 2000
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Ingår i: Tetrahedron. - 0040-4020 .- 1464-5416. ; 56:13, s. 1911-1916
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Tidskriftsartikel (refereegranskat)abstract
- 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.
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