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pHarmacist (pHantasticant) 08-26-03 12:43 No 455754 |
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Great synthetic approach to 4-subst. indoles (Rated as: excellent) |
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Fellow Tryptamine Bees! This is an interesting reduction of indole with Li in the presence of trimethylsilyl chloride, followed by rearomatisation that give you 4-methylsilylindole an excellent intermediate used in the synthesis of 4-substituted indoles via electrophilic replacement of silicon. Preparation and Reactions of 4-(Trimethylsilyl)indole Anthony G. M. Barrett, Daniel Dauzonne, Ian A. O'Neil, Alain Renaud J. Org. Chem. 49, 4409-4415 (1984) (../rhodium/pdf /4-tms-indole Abstract: Indole or 1-(trimethylsilyl)indole was reacted sequentially with lithium-chlorotrimethylsilane and with 1,4-benzoquinone to produce 1,4-bis(trimethylsilyl)indole (50% and 55%, respectively). Methanolysis gave 4-(trimethylsilyl)-indole which reacted with electrophiles at C-3. However, the derivative l-acetyl-4-(trimethylsilyl)indole reacted with acetyl, 2-chloropropanoyl, or propenoyl chlorides via clean C-4 ipso substitution. Attempts to extend the reaction to a useful synthesis of derivatives of 5-oxo-1,3,4,5-tetrahydrobenz[cd]indole, a lysergic acid synthon, were prevented by low yields. ______ See also: Post 443497 (pHarmacist: "Large-scale syntheses of Psilocin/Psilocybin", Tryptamine Chemistry) Do NOT disturb: Mind at Large |
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pHarmacist (pHantasticant) 11-04-03 22:23 No 468775 |
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Uhle's approach to 4-Substituted Indoles (old) (Rated as: excellent) |
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Failed to find this using TFSE, if posted b4 - delete: The Synthesis of S-Keto-l,3,4,5-tetrahydrobenz[cd]indole. Frederick C. Uhle JOACS VOLUME 71 MARCH 19, 1949 NUMBER 3 (http://pharmacist-hive.tripod.com/uhle. http://www.bassdrive.com/BassDrive.m3u |
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pHarmacist (pHantasticant) 11-11-03 16:01 No 470209 |
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3- and 4-substituted indoles (towards Ergot alk.) (Rated as: good read) |
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TFSE gave no relevant hits, thus: ГАлллллл
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hest (Hive Adickt) 11-11-03 18:55 No 470244 |
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4-oh-indole | ||||||
Hi PH.. Good to see someone looking at this wonderfull indole. Doo you have a good way to the 2,6-nitro-toluene ? Dinitration of toluene and seperation of the isomeres have alwayes seem a bid diff. to mee. The Azide routhe from salicylaldehyde i still my favorite. |
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Rhodium (Chief Bee) 11-11-03 21:28 No 470266 |
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2,6-dinitrotoluene from tosic acid | ||||||
What about dinitrating para-toluenesulfonic acid, then desulfonate? |
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