826-67-5

Upstream product

• 408314-99-8 5-methoxybenzo[cd]indol-2(1H)-one 
• 582319-19-5 1,3,4,5-tetrahydro-benz[cd]indole-2-carboxylic acid 
• 126266-29-3 1-Azidomethylene-1,2,3,4-tetrahydronaphthalene 
• 1984-02-7 5-isocyano-1,2,3,4-tetrahydronaphthalene 
• 96679-56-0 1-(4,5-dihydro-3H-benzo[cd]indol-1-yl)ethanone 
• 1112057-14-3 C₁₆H₂₃NO₄ 
• 94734-30-2 5-hydroxy-1H-benz[cd]indol-2-one 
• 29809-14-1 5-nitro-1,2,3,4-tetrahydronaphthalene 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 128405-62-9 1-Azidomethyl-1,2,3,4-tetrahydronaphthalen-1-ol 
• 51605-29-9 Spiro<1,2,3,4-tetrahydronaphthalene-1,2'-oxirane> 
• 138343-72-3 2-Hydroxy-2a,3,4,5-tetrahydro-2H-benzo[cd]indole-1-carboxylic acid tert-butyl ester 
• 138343-71-2 1-(tert-butoxycarbonyl)-5,6,7,8-tetrahydronaphthylamine 
• 2217-41-6 1-amino-5,6,7,8-tetrahydronaphthalene 

Relevant academic research and scientific papers

A microwave assisted intramolecular-furan-Diels-Alder approach to 4-substituted indoles

The key steps of a versatile new protocol for the convergent synthesis of 3,4-disubstituted indoles are the addition of an α-lithiated alkylaminofuran to a carbonyl compound, a microwave-accelerated intramolecular Diels-Alder cycloaddition and an in situ

Synthesis of indoles via 6π-electrocyclic ring closures of trienecarbamates

A new method for the preparation of indoles from readily available α-haloenones and α-(trialkylstannyl)enecarbamates is described. Following a Stille coupling, trienecarbamate 2 is electronically activated to undergo a facile 6π-electrocyclic ring closure

Preparation of indoles and oxindoles from N-(tert-butoxycarbonyl)-2-alkylanilines

Treatment of dilithiated N-(tert-butoxycarbonyl)anilines 1 with dimethylformamide or carbon dioxide furnishes intermediates 3, 5, that are easily converted to N-(tert-butoxycarbonyl)indoles 4 and oxindoles (indol-2(3H)-ones, 7), respectively. Condensation of dilithiated 1 with N-methoxy-N-methylamides provides ketones 9 which are cyclized upon trifluoroacetic acid treatment to either 2-substituted 1-(tert-butoxycarbonyl)indoles 10 or 2-substituted indoles 11 depending on the reaction time. This general methodology has been applied to efficient synthesis of 1,2-alkyl-bridged indoles 12, 1,3,4,5-tetrahydrobenz[c,d]indole (16), 2a,3,4,5-tetrahydrobenz[c,d]indol-2(1H)-one (18), and 1-(tert-butoxycarbonyl)1H-pyrrolo[2,3-b]pyridine (21).

Preparation of Tetrahydrobenzindoles from 1-Tetralones

3,4-Bridged indoles (5) are prepared from readily available aromatic ketones (1) by conversion into the epoxides (2), ring opening with azide ion to give the azido alcohols (3), dehydration, and thermolysis of the resulting vinyl azides (4).

PREPARATION OF TETRAHYDROBENZINDOLES FROM 1-TETRALONES

3,4-Bridged indoles (5) are prepared from readily available aromatic ketones (1) by conversion into epoxides, ring opening with azide ion, dehydration, and thermolysis of the resulting vinyl azides.

BENZINDOLES - I. THE USE OF TERT-BUTOXY-BIS(DIMETHYLAMINO)METHANE AS CONDENSATION REAGENT.

A simple and efficient route to benzindoles is the reaction of nitrotetralins with Bredereck's reagent and reduction of the condensation product to the corresponding annelated indole.

INDOLE SYNTHESES UTILIZING o-METHYLPHENYL ISOCYANIDES.

New indole synthesis starting with o-methylphenyl isocyanides such as o-tolyl, 2,4-xylyl, and 2,6-xylyl isocyanide is described. Treatment of o-tolyl isocyanide with LDA in diglyme at minus 78 degree C generated selectively o-(lithiomethyl)phenyl isocyanide in an almost quantitative yield, which on warming up to room temperature was cyclized to indole after aqueous workup. Similarly, 2,4-xylyl and 2,6-xylyl and 2,6-xylyl isocyanides were cyclized to 5-methylindole and 7-methylindole quantitatively. The o-(lithiomethyl)phenyl isocyanides reacted with electrophiles such as alkyl halides and alkylene oxides to give o-alkylphenyl isocyanides, which were cyclized via the lithiation at the orthobenzylic carbon to afford 3-substituted indoles.