188064-71-3

Upstream product

• 548448-36-8 N,N-bis-(3,4-dimethoxy-β-phenylethyl)-o-phthalamide 
• 85-44-9 phthalic anhydride 
• 63375-81-5 2-(2-bromo-4,5-dimethoxyphenylphenyl)ethan-1-amine 
• 493-49-2 6,7-dimethoxy-3,4-dihydro-2H-isoquinolin-1-one 

Relevant academic research and scientific papers

Synthesis of bis-Tetrahydroisoquinolines Based on Homoveratrylamine and Dibasic Acids. 2.

Bis-tetrahydroisoquinolines were prepared from homoveratrylamine and phthalic acids using a Bischler-Napieralski reaction. Their structures were confirmed by IR and NMR spectral data.

Bronsted acid assisted activation of imide carbonyl group: Regioselective synthesis of isoindoloisoquinolinone alkaloid (±)-nuevamine

Activation of imide carbonyl group with trifluoromethanesulfonic acid facilitates the intramolecular cyclization of phenethylphthalimides to give a fused isoindoloisoquinolinone skeleton. The first one pot regioselective synthesis of isoindoloisoquinolinone alkaloid (±)-nuevamine has been successfully executed using this methodology.

Construction of the six- and five-membered aza-heterocyclic units of the isoindoloisoquinolone nucleus by parham-type cyclization sequences - Total synthesis of nuevamine

An efficient methodology for the synthesis of isoindolo[1,2-α] isoquinolones based on two Parham-type cyclizations allowing the formation of the five- and six-membered nitrogenated rings from carbamate or diacylamine precursors is described. The synthetic potential of this method has been further illustrated by the total synthesis of the alkaloid nuevamine. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

Metalation vs Nucleophilic Addition in the Reactions of N-Phenethylimides with Organolithium Reagents. Ready Access to Isoquinoline Derivatives via N-Acyliminium Ions and Parham-Type Cyclizations

Sequential carbophilic addition of organolithium reagents and N-acyliminium ion cyclization of N-phenethylimides 1 affords the substituted isoquinolones 3 in high yields, with the possibility of varying the substituent at the C-1 position of the isoquinoline ring by changing the organolithium reagent. Ready access to the isoquinoline nucleus via Parham-type cyclization of imides 2 is also described. We have shown that iodinated imides 2 tolerate the metal-halogen exchange in the presence of the imide group, and the intramolecular cyclization of the so-obtained aromatic organometallic derivatives leads to the corresponding enamides 4. Both approaches have allowed the efficient preparation of various types of the isoquinoline class of alkaloids, just by changing the substitution pattern on the readily available starting imides. Thus, we have developed convenient alternative routes for the synthesis of benzo[a]quinolizidones and their 2-oxa analogs, isoindoloisoquinolones, dibenzo[a,h]quinolizidones, and thiazolo- and oxazolo[4,3-a]isoquinolones.

Parham-type cyclization and nucleophilic addition-N-acyliminium ion cyclization sequences for the construction of the isoquinoline nucleus

Efficient methodologies based on the nucleophilic addition-N-acyliminium ion cyclization and the Parham-type cyclization sequences of N-phenethylimides 1 and 2 are reported for the synthesis of a dibenzo[a,h]quinolizidones, thiazolo-, oxazolo-, and imidazolo[4,3-a]isoquinolones.