552-29-4

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 77, p. 4399, 1955 DOI: 10.1021/ja01621a062

InChI:InChI=1/C11H11NO3/c1-12-3-2-7-4-9-10(15-6-14-9)5-8(7)11(12)13/h4-5H,2-3,6H2,1H3

Upstream product

• 6592-85-4 hydrastinine 
• 298-45-3 (S)-bulocapnine 
• 53777-79-0 N-methyl-13,14-dehydrostylopinium chloride 
• 21796-14-5 noroxyhydrastinine 
• 74-88-4 methyl iodide 
• 35287-11-7 6-methyl-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-6-ium iodide 
• 124-40-3 dimethyl amine 
• 494-55-3 N-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline 
• 33542-98-2 β-<3,4-(methylenedioxy)phenyl>ethyl formamide 
• 94-53-1 Piperonylic acid 
• 86138-63-8 6,7-dihydro-indeno[5,6-d][1,3]dioxol-5-one oxime 
• 130-86-9 protopine 
• 24880-42-0 6-methyl[1,3]dioxolo[4,5-g]isoquinolin-5(6H)-one 
• 28281-84-7 2-carboxy-4,5-methylenedioxyphenylacetic acid 

Downstream Products

• 6592-85-4 hydrastinine 
• 1132791-32-2 C₁₇H₁₅NO₃ 
• 1132791-33-3 C₁₉H₁₇NO₄ 
• 1132791-37-7 C₁₇H₁₄BrNO₃ 
• 1132791-35-5 C₁₈H₁₇NO₄ 
• 1132791-34-4 C₂₀H₁₉NO₅ 
• 1132791-36-6 C₁₈H₁₄F₃NO₄ 

Relevant academic research and scientific papers

Facile synthesis of the isoquinoline alkaloids doryanine and oxyhydrastinine

Starting from 4,5-(methylenedioxy)homophthalic acid, a concise and efficient synthesis of the isoquinoline alkaloids doryanine and oxyhydrastinine is described via the corresponding homophthalimide utilizing a one-pot regioselective reductive dehydration

Pd-catalyzed ortho-arylation of 3,4-dihydroisoquinolones via C-H bond activation: synthesis of 8-aryl-1,2,3,4-tetrahydroisoquinolines

An efficient route to synthesize biologically interesting 8-aryl-1,2,3,4-tetrahydroisoquinoline has been developed. It involves the Pd-catalyzed direct arylation of 3,4-dihydroisoquinolones via C-H bond activation with aryl iodides to afford a variety of 8-arylated cross-coupling products, which are subsequently reduced to 8-aryl-1,2,3,4-tetrahydroisoquinolines in good to excellent yields.

Activation of iodosobenzene by catalytic tetrabutylammonium iodide and its application in the oxidation of some isoquinoline alkaloids

Oxidation of N-methyltetrahydroisoquinolines with iodosylbenzene in the presence of a catalytic amount of tetrabutylammonium iodide in various solvents afforded N-methyl-2H-3,4-dihydroisoquinol-1-ones in almost quantitative yields. The application of this finding to the oxidation of other isoquinolines, including tetrahydroisoquinolines, lycorine diacetate, and benzyltetrahydroisoquinolines, also afforded the corresponding lactams in good yields, however, accompanied by a few minor byproducts. Under similar conditions, tetrahydroberberine gave a rearranged compound, berberal, as the major product, accompanied by 8-oxoberberine and berberine.

A Facile Total Synthesis of Isoquinolone Alkaloids

Four isoquinolone alkaloids, N-methylcorydaldine 8a, oxyhydrastinine 8b, 6,7-dimethoxy-2-methylisocarbostyril 9a and doryanine 9b, have been efficiently synthesized from phenyl vinyl sulfoxide via the Pummerer type rearrangement as a key step.

Mercuric dehydrogenations of N-tertiary piperidine derivatives with different substitution pattern

A comparison of the dehydrogenation of different N-tertiary piperidine derivatives with mercuric EDTA and mercuric acetate shows an increase of the reaction with the complex method.This is especially evident with the N-demethylation of 1,2,2,6,6-pentamethylpiperidine.Generally with dehydrogenations offering a possibility of generating a tertiary or a secondary carbenium ion, the latter alternative is mostly also realized to a minor extent.

OXIDATION OF 3,4-DIHYDROISOQUINOLINIUM SALT WITH DMSO/conc HCl

3,4-Dihydroisoquinolinium salts can be oxidized to the corresponding isoquinolines by DMSO in conc HCl.

New Facile Synthesis of Isoquinolone Alkaloids

Beckmann rearrangement of substituted indanone oximes (IIa, b) with PPA gives corydaldine (IIIa) and noroxyhydrastinine (IIIb) which on methylation yield N-methylcorydaldine (IVa) and N-methylnoroxyhydrastinine (IVb) respectively.

Air oxidation of Reissert compounds

Reissert compounds undergo autoxidation in basic solution giving rise to isoquinaldo- or quinaldonitriles.Under the same reaction conditions, dihydroisoquinoline Reissert compounds undergo oxidative decyanation to dihydroisocarbostirils.The intermediacy of α-peroxycyanides is proposed in this transformation.