Synthese von 1,4-Diazepino[1,2-a]-indolen
Condensation of 1-(3-aminopropyl)-3-methyl-indole (1) with acetaldehyde or benzaldehyde by the Mannich reaction gave 1,4-diazepino[1,2-a]-indoles 2 and 3 respectively. The 1,4-diazepino[1,2-a]indole 9 was obtained by analogous acidcatalyzed cyclo-condensation of 1 with dimethyl-2-dimethoxyethylmalo...
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| Format: | Article |
| Language: | deu |
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Swiss Chemical Society
1977-09-01
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| Series: | CHIMIA |
| Online Access: | https://www.chimia.ch/chimia/article/view/9390 |
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| _version_ | 1850140296177778688 |
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| author | Hans Peter Härter Othmar Schindler |
| author_facet | Hans Peter Härter Othmar Schindler |
| author_sort | Hans Peter Härter |
| collection | DOAJ |
| description |
Condensation of 1-(3-aminopropyl)-3-methyl-indole (1) with acetaldehyde or benzaldehyde by the Mannich reaction gave 1,4-diazepino[1,2-a]-indoles 2 and 3 respectively.
The 1,4-diazepino[1,2-a]indole 9 was obtained by analogous acidcatalyzed cyclo-condensation of 1 with dimethyl-2-dimethoxyethylmalonate (8), and 6,17, and 19 were obtained by intramolecular condensation of 5, 15, and 16 respectively. All these lactames could be readily reduced to the corresponding bases 7, 12, 18 and 20. Bischler-Napieralsky cyclization of 23 gave the diazepinoindole-butanoic acid derivative 25 as main product, together with the fully cyclized 24. Compound 25, after reduction, gave directly the diazepinoindole 26, which was also obtained by reduction of compound 24.
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| format | Article |
| id | doaj-art-6d17bc2269354ce3a3ca192fa4d2ccea |
| institution | OA Journals |
| issn | 0009-4293 2673-2424 |
| language | deu |
| publishDate | 1977-09-01 |
| publisher | Swiss Chemical Society |
| record_format | Article |
| series | CHIMIA |
| spelling | doaj-art-6d17bc2269354ce3a3ca192fa4d2ccea2025-08-20T02:29:54ZdeuSwiss Chemical SocietyCHIMIA0009-42932673-24241977-09-0131910.2533/chimia.1977.362Synthese von 1,4-Diazepino[1,2-a]-indolenHans Peter Härter0Othmar Schindler1Forschungsinstitut Wander (eine Sandoz Forschungsgruppe), Bern, SchweizForschungsinstitut Wander (eine Sandoz Forschungsgruppe), Bern, Schweiz Condensation of 1-(3-aminopropyl)-3-methyl-indole (1) with acetaldehyde or benzaldehyde by the Mannich reaction gave 1,4-diazepino[1,2-a]-indoles 2 and 3 respectively. The 1,4-diazepino[1,2-a]indole 9 was obtained by analogous acidcatalyzed cyclo-condensation of 1 with dimethyl-2-dimethoxyethylmalonate (8), and 6,17, and 19 were obtained by intramolecular condensation of 5, 15, and 16 respectively. All these lactames could be readily reduced to the corresponding bases 7, 12, 18 and 20. Bischler-Napieralsky cyclization of 23 gave the diazepinoindole-butanoic acid derivative 25 as main product, together with the fully cyclized 24. Compound 25, after reduction, gave directly the diazepinoindole 26, which was also obtained by reduction of compound 24. https://www.chimia.ch/chimia/article/view/9390 |
| spellingShingle | Hans Peter Härter Othmar Schindler Synthese von 1,4-Diazepino[1,2-a]-indolen CHIMIA |
| title | Synthese von 1,4-Diazepino[1,2-a]-indolen |
| title_full | Synthese von 1,4-Diazepino[1,2-a]-indolen |
| title_fullStr | Synthese von 1,4-Diazepino[1,2-a]-indolen |
| title_full_unstemmed | Synthese von 1,4-Diazepino[1,2-a]-indolen |
| title_short | Synthese von 1,4-Diazepino[1,2-a]-indolen |
| title_sort | synthese von 1 4 diazepino 1 2 a indolen |
| url | https://www.chimia.ch/chimia/article/view/9390 |
| work_keys_str_mv | AT hanspeterharter synthesevon14diazepino12aindolen AT othmarschindler synthesevon14diazepino12aindolen |