83402-24-8

Upstream product

• 41455-40-7 4-amino-5,5-ethylenedioxy-1-(toluene-4-sulfonyl)-3,4-dihydro-1H-benzo[c,d]indole 
• 64-18-6 formic acid 
• 109-94-4 formic acid ethyl ester 
• 3744-82-9 3,4-dihydrobenzo[cd]indol-5(1H)-one 
• 849413-44-1 4-azido-5,5-ethylenedioxy-1-(toluene-4-sulfonyl)-3,4-dihydro-1H-benzo[c,d]indole 
• 98-59-9 p-toluenesulfonyl chloride 
• 81206-38-4 4-azido-1-(toluene-4-sulfonyl)-3,4-dihydro-1H-benzo[c,d]indol-5-one 
• 37945-51-0 4-bromo-1-(toluene-4-sulfonyl)-3,4-dihydro-1H-benzo[c,d]indol-5-one 
• 37945-46-3 1-(toluene-4-sulfonyl)-3,4-dihydro-1H-benzo[c,d]indol-5-one 
• 108-24-7 acetic anhydride 

Downstream Products

• 849413-50-9 4-[N-(methyl)-N-propargyl]amino-5,5-ethylenedioxy-1-(toluene-4-sulfonyl)-3,4-dihydro-1H-benzo[c,d]indole 
• 744970-29-4 4-[N-(methyl)-N-acetonyl]amino-5,5-ethylenedioxy-1-(toluene-4-sulfonyl)-3,4-dihydro-1H-benzo[c,d]indole 

Relevant academic research and scientific papers

Chemistry of indoles carrying a basic function. Part IX. Unexpected cyclizations of diketones derived from Uhle's ketone

Starting from a tricyclic diketone (14) obtained by Bowman's method, a tetracyclic oxonaphthalene derivative (17) has been prepared through intramolecular aldol condensation followed by indole → naphthalene isomerization. An unexpected formation of a lact

Experiments Towards the Synthesis of the Ergot Alkaloids and Related Structures. Part 4. Lysergic Acid-An Attempted 'Endo-amide' Approach

Two attempts to synthesise the tricyclic α-keto-amide (6) are described.In the first, 1,2,3,4-tetradihydro-2-methylaminonaphthalen-1-one (3) was allowed to react with pyridine-hydroxymaleic anhydride at -20 deg C and then at room temperature to give a complex mixture from which the naphth-1,4-oxazinone (14), 2-pyruvamido-1-tetralone (16; R=Ac) contaminated with the oxazinone (14) and the phenolic acid (13c) were isolated.A tetracyclic oxazinone was also obtained from the appropriate methylaminotetrahydroacenaphthenone but not from the corresponiding benzindolone (7; R=NHMe.HCl).In the second, the N-methyldione (10) was converted in three stages into the tricyclic acid (13c) which proved unexpectedly stable.However, its triethylamine salt lost carbon dioxide at 140 deg C to give not the required keto-amide (6) but the isomeric hydroxybenzquinolone (13d).Both the oxazinone (14) and the impure pyruvamido-ketone (16; R=Ac) were converted within seconds by treatment with 2 M-sodium hydroxide into the sparingly soluble sodium salt of the phenol (13d) as was the pure pyruvamido ketone whose synthesis is described.