123355-84-0

Upstream product

• 186581-53-3 diazomethane 
• 56114-05-7 1-<2-(4-hydroxy-3-methoxy)ethyl>-7-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline 
• 20226-10-2 1-<2-(3,4-dimethoxyphenyl)ethyl>-3,4-dihydro-6,7-dimethoxy-2-methylisoquinolinium iodide 
• 20944-14-3 1-[2-(3,4-dimethoxyphenyl)-ethyl]-6,7-dimethoxy-3,4-dihydroisoquinoline 
• 50896-90-7 (-) N-norlaudanosine 
• 4525-33-1 dimethyl dicarbonate 
• 15248-39-2 6,7-dimethoxyisoquinoline 
• 123355-83-9 (1S,4R)-1-<(1R)-1,2,3,4-Tetrahydro-6,7-dimethoxy-1-<2-(3,4-dimethoxyphenyl)-1-ethyl>-2-isoquinolylcarbonyl>-4,7,7-trimethyl-2-oxa-bicyclo<2.2.1>heptan-3-one 
• 123279-31-2 (1S,4R)-1-<1,2,3,4-Tetrahydro-6,7-dimethoxy-1-<2-(3,4-dimethoxyphenyl)-2-oxo-1-ethyl>-2-isoquinolylcarbonyl>-4,7,7-trimethyl-2-oxa-bicyclo<2.2.1>heptan-3-one 
• 4302-52-7 4-ethynylveratrole 
• 2316-26-9 3,4-dimethoxycinnamic acid 
• 1374870-00-4 6,7-dimethoxy-1-(3,4-dimethoxyphenylethynyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 111427-24-8 N-<3-(3,4-dimethoxyphenyl)propionyl>-2-thiazolidine-2-thione 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 

Downstream Products

• 105578-49-2 (+/-)-N,N-Dimethyl-6,7,3',4'-tetramethoxyphenylethyl-1,2,3,4-tetrahydroisoquinolinium iodide 
• 97117-83-4 3-(3,4-Dimethoxy-phenyl)-1-<4,5-dimethoxy-2-<2-(methyl-aethoxycarbonyl-amino)-aethyl>-phenyl>-propen-(1) 

Relevant academic research and scientific papers

Succinct Syntheses of Methopholine, (±)-Homolaudanosine, and (±)-Dysoxyline via Metal-free One-Pot Double Alkylation on 1-Methyl-3,4-dihydroisoquinolines

A mild one-pot and metal-free condition was discovered to implement two different alkyl groups chemoselectively on 1-methyl-3,4-dihydroisoquinoline (1-Me-DHIQ), one at the nitrogen another at the C1-methyl group. This chemistry is compatible with various DHIQs as well as alkyl halides. Application of this chemistry facilitated the concise syntheses of methopholine, (±)-homolaudanosine, and (±)-dysoxyline, requiring only two steps from 6,7-dimethoxy-1-Me-DHIQ.

Biomimetic Total Synthesis of Dysoxylum Alkaloids

A five-step total synthesis of Dysoxylum alkaloids has been achieved using a biomimetic approach from zanthoxylamide protoalkaloids. The synthesis featured a direct amidation and a Bischler-Napieralski reaction to form the dihydroisoquinoline ring, which

Unified approach to isoindolinones and THIQs via lewis acid catalyzed domino mukaiyama-mannich Lactamization/Alkylations: Application in the synthesis of (±)-homolaudanosine

A novel and efficient synthesis of a variety of isoindolinones and tetrahydroisoquinolines via a Lewis acid catalyzed domino Mukaiyama-Mannich lactamization/alkylation is achieved. This transformation comprises a sequential formation of three new bonds through a one-pot, three-component procedure to afford product in moderate to high yields. A concise synthesis of (±)-homolaudanosine (2b) has been achieved using this method.

Practical metal-free C(sp3)-H functionalization: Construction of structurally diverse α-substituted N-benzyl and N-allyl carbamates

Described is a practical and universal C-H functionalization of readily removable N-benzyl and N-allyl carbamates, with a wide range of nucleophiles at ambient temperature promoted by Ph3CClO4. The metal-free reaction has an excellent functional-group tolerance, and displays a broad scope with respect to both N-carbamates and nucleophile partners (a variety of organoboranes and C-H compounds). The synthetic utility in target- as well as diversity-oriented syntheses is demonstrated. Strategic play: A direct functionalization of the title carbamates with a wide range of nucleophiles has been developed. The reaction proceeds efficiently at low temperature using Ph3CClO4 as an oxidant. Sensitive functional groups are tolerated, thus allowing applications in natural product synthesis, the construction of chemical libraries, and the discovery of potential anticancer targets.

C-1 alkynylation of N-methyltetrahydroisoquinolines through CDC: A direct access to phenethylisoquinoline alkaloids

Direct cross-coupling between N-methyltetrahydroisoquinolines and alkynes using CuI-DEAD is presented. It affords the regioselective C-1-alkynylated products in good yield. This regio-selectivity is in contrast to the results reported earlier in the reaction of N,N-dimethylbenzyl amine where the N-methyl alkynylated product was formed exclusively or predominantly. The C-1-substituted propargylic isoquinolines were easily reduced to phenethylisoquinolines with Pd/C. This reaction sequence provides a short route to synthesize methopholine, homolaudanosine and other phenethylisoquinoline alkaloids. Georg Thieme Verlag Stuttgart · New York.

Enantioselective addition of terminal alkynes to isolated isoquinoline iminiums

(Chemical Equation Presented) The asymmetric, catalytic addition of terminal alkynes to discrete alkyliminium species in the presence of copper bromide, QUINAP ligand, and triethylamine is reported. The reaction proceeds in high yield and high enantiomeri

Synthesis and radioligand binding studies of methoxylated 1,2,3,4-tetrahydroisoquinolinium derivatives as ligands of the apamin-sensitive Ca2+-activated K+ channels

Several methoxylated 1,2,3,4-tetrahydroisoquinoliniums derived from N-methyl-laudanosine and N-methyl-noscapine were synthesized and evaluated for their affinity for apamin-sensitive binding sites. The quaternary ammonium derivatives have a higher affinit

Asymmetric addition of nucleophiles to C-1 position of isoquinolines using (S)-alanine derivatives as chiral auxiliaries

5,8-Dibromoisoquinoline derivatives were allowed to react with a nucleophile (silyl enol ether or allyltributyltin) in the presence of an acyl chloride derived from (S)-alanine to afford the 1,2-addition products in good chemical yields and high stereoselectivity. The bromo groups were readily removed by a reduction process in which the double bond at C3-C4 was also reduced. Thus the reaction system provided a general method to synthesize asymmetric 1-substituted tetrahydroisoquinolines. In order to determine the absolute configuration of the reaction product, (-)-homolaudanosine was synthesized in an enantiopure form. The stereoselectivity was rationally understood from the conformation of intermediary N-acylated isoquinolinium salts.

A novel straightforward synthesis of enantiopure tetrahydroisoquinoline alkaloids

A novel, direct, and high-yielding stereoselective method for enantiopure 1-substituted tetrahydroisoquinolines (THIQ) is described. The successful approach, which creates the stereocenter during the formation of the THIQ nucleus is based on (i) formation of chiral 2,3-substituted perhydro-1,3-benzoxazines derived from (-)-8-aminomenthol, (ii) diastereoselective intramolecular ring opening of the N,O-acetal moiety by an arylmetal generated from the substituent at the nitrogen atom in the perhydrobenzoxazine ring, and (iii) removal of the chiral auxiliary appendage. The starting perhydrobenzoxazines are easily prepared from (-)-8-aminomenthol and two different aldehydes, and the intramolecular opening is stereospecific, leading to a single stereoisomer. The method allows the preparation of a wide variety of enantiopure 1-substituted THIQ, with different substituents at C-1, by changing the nature of the starting aldehydes.

A novel synthesis of chiral tetrahydroisoquinolines employing silyl enol ethers in the presence of chiral acyl chlorides

6,7-Dimethoxyisoquinoline derivatives reacted with silyl enol ethers in a highly diastereoselective manner in the presence of an acyl chloride derived from L-alanine. (-)-Homolaudanosine was synthesized in an enantiopure form from 6,7-dimethoxyisoquinoline via six steps using this method.