36209-71-9

Usage

InChI:InChI=1/C12H15NO3/c1-8(13-9(2)14)5-10-3-4-11-12(6-10)16-7-15-11/h3-4,6,8H,5,7H2,1-2H3,(H,13,14)

Upstream product

• 4764-17-4 3,4-methylenedioxyamphetamine 
• 108-24-7 acetic anhydride 
• 5438-41-5 2-nitro-1-(3,4-methylenedioxyphenyl)-1-propene 
• 87095-03-2 5-(2-nitropropyl)benzo[d][1,3]dioxole 
• 4676-39-5 1-(1,3-benzodioxol-5-yl)-2-propanone 
• 5438-41-5 5-(2-nitroprop-1-enyl)benzo[d][1,3]dioxole 

Downstream Products

• 14089-52-2 3,4-methylenedioxyethylamphetamine 

Relevant academic research and scientific papers

Transformation of oximes of phenetyl ketone derivatives to quinolines and azaspirotrienones catalyzed by tetrabutylammonium perrhenate and trifluoromethanesulfonic acid

Phenethyl ketone oximes are converted to quinolines by the treatment with tetrabutylammonium perrhenate, trifluoromethanesulfonic acid, and chloranil in refluxing 1,2-dichloroethane. Azaspirotrienones can be synthesized from p-hydroxyphenethyl or 3-(p-hydroxyphenyl)propyl ketone oximes by applying the above method. Thus prepared azaspirotrienones are converted to quinolines by acid treatment.

Synthesis of Quinolines via Intramolecular Cyclization of Benzylacetone Oxime Derivatives Catalyzed with Tetrabutylammonium Perrhenate(VII) and Trifluoromethanesulfonic Acid

Intramolecular cyclization reaction on the nitrogen atom of benzylacetone oxime derivatives, which have electron donating group(s) on the phenyl group, proceeds by treatment with tetrabutylammonium perrhenate, trifluoromethanesulfonic acid, and 4-chloranil in refluxing 1,2-dichloroethane to afford quinoline derivatives in good yield.

Reaction of a Possible Iminoketene Precursor with 6,7-Dialkoxy-1,3-dialkyl-3,4-dihydroisoquinolines

Reaction of 6,7-dialkoxy-1-alkyl-3,4-dihydro-3-methylisoquinolines (10 - 12) with sulphinamide anhydride (13) yields 2,3-dialkoxy-5,6,7,8-tetrahydro-6-methyl-8-oxoisoquinolinoquinazolines (14 and 19) and 2,3-dialkoxy-13a-alkyl-5,6,7,8,13,13a-hexahydro-6-methyl-8-oxoisoquinolinoquinazolines (15 - 17 and 20).Of the two possible geometrical isomers of the latter class of compounds, the cis-isomer predominates and the trans-isomer is found to be labile towards aerial oxidation.No evidence for the generation of iminoketene (21) is obtained in the reaction of sulphinamide anhydride (13) with various 3,4-dihydroisoquinoline derivatives.

Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine)

The known central nervous system activity of 3,4-methylenedioxyphenylisopropylamine and its N-methyl homolog prompted the synthesis of a series of analogs with substituents on the nitrogen atom. Most of these analogs (R = alkyl, alkenyl, hydroxy, alkoxy, and alkoxyalkyl) were prepared by the reductive alkylation of 3,4-methylenedioxyphenylacetone with the appropriate amine and sodium cyanoborohydride. Hindered isomers were synthesized indirectly. Measurements of their pharmacological activity in several animal assays and in human subjects indicated that the central activity decreased with the increasing bulk of the N-substituent.