19260-06-1

Upstream product

• 19209-03-1 2-nitro-N-(2-phenylethyl)benzamide 
• 156-28-5 2-phenylethylamine hydrochloride 
• 304463-98-7 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-N-phenethyl-benzamide 
• 19050-62-5 N-(2-phenylethyl)-2-aminobenzamide 
• 118-48-9 isatoic anhydride 
• 552-16-9 ortho-nitrobenzoic acid 
• 610-14-0 2-nitrobenzyl chloride 
• 64-04-0 phenethylamine 
• 19007-73-9 1-(2'-nitrophenyl)-3,4-dihydroisoquinoline 
• 304463-99-8 1-(2-N-phthalimidophenyl)-3,4-dihydroisoquinoline 

Downstream Products

• 596087-07-9 1-(2-[(R)-O-acetylmandelyl]aminophenyl)-3,4-dihydroisoquinoline 
• 548459-37-6 (S)-1-(2-[(R)-O-acetylmandelyl]aminophenyl)-1,2,3,4-tetrahydroisoquinoline 
• 19007-80-8 1-(2-aminophenyl)-1,2,3,4-tetrahydroisoquinoline 
• 29483-64-5 N-[2-(3,4-dihydro-isoquinolin-1-yl)-phenyl]-acetamide 

Relevant academic research and scientific papers

Divergent Syntheses of Pyridoacridine Alkaloids via Palladium-Catalyzed Reductive Cyclization with Nitro-Biarenes

A divergent and novel protocol for the preparation of both pyrido[2,3,4-kl]acridine and pyrido[4,3,2-kl]acridine alkaloids was developed. This method featured the remote palladium-catalyzed reductive cyclization with Mo(CO)6 as reductant. A wide range of substrates including three types of nitro arenes were tolerated and afforded corresponding products in good to excellent yields. This method has been successfully applied to the total synthesis of norsegoline, styelsamine C and the skeleton of necatorone.

The synthesis of N-phenoxyethyl-1-substituted-1,2,3,4-tetrahydroisoquinolines and their α1-adrenoceptor blocking activity

A series of phenoxyisoquinolines, N-phenoxyethyl-1-(2-nitrophenyl)-1,2,3,4-THIQs 3a-3d, N-phenoxyethyl-1-benzyl-1,2,3,4-THIQ 3e, N-phenoxyethyl-1-(2-aminophenyl)-1,2,3,4-THIQs 5f-5i, N-phenoxyethyl-1-(2-phenoxyethylaminophenyl)-1,2,3,4-THIQs 5f′-5i′, have

Synthesis and?antitumor activity of?cis-dichloroplatinum(II) complexes of?1-(2-aminophenyl)-1,2,3,4-tetrahydroisoquinolines

Fifteen cis-dichloroplatinum complexes (5a-5o) were synthesized by treatment of 1-(2-aminophenyl)-1,2,3,4-THIQs (4a-4o) with K2PtCl4. The antitumor activity of these compounds was examined against four different human tumor cell lines. Their structure-activity relationships for antitumor activity are reported. All of these compounds exhibited activity against MCF-7 cell line and showed good activity against WiDr cell line except 5c and 5f. On the other hand, compounds 5j and 5o are more active than the other compounds against Hepa59T/VGH cell line. The electron-donating group at the 6-position of isoquinoline ring seems to decrease the antitumor activity and the chloro substituent at the C-4 position of the aniline ring shown the highest potency. The "trans influence" dominates the control of the stability of [1-(2-aminophenyl)-1,2,3,4-THIQ]dichloroplatinums(II).

A novel synthesis of 5,6-dihydroindazolo[3,2-a]isoquinolines and their relative compounds via tin(II) chloride dihydrate as reducing agent

A series of 1-(2-nitrophenyl)-3,4-dihydroisoquinolines were reduced under very mild reaction conditions in the presence of Tin(II) chloride dihydrate (SnCl2·2H2O) to give 5,6-dihydroindazolo[3,2-a] isoquinolines 4a-h. A mechanism for

Synthesis of racemic 1,2,3,4-tetrahydroisoquinolines and their resolution

1-Aniline-substituted 3,4-dihydroisoquinolines were obtained in various ways using the Bischler-Napieralski reaction. The effect of the protecting group at the aniline nitrogen atom on the course of the reaction has been studied and it was found that the N-phthalyl group was stable under the cyclization conditions. The dihydroisoquinolines were reduced to the racemic 1,2,3,4-tetrahydroisoquinolines which were resolved by crystallization of the diastereomeric tartrates. Two examples of 1,2,3, 4-tetrahydroisoquinolines were obtained in optically pure form (>99% ee).

Substituted isoquinolines by Noyori transfer hydrogenation: Enantioselective synthesis of chiral diamines containing an aniline subunit

Transfer hydrogenation using the Noyori catalyst 5-Ts is effective for the enantioselective hydrogenation of imines containing fully substituted nitrogen groups (12 or 13). Analogues such as 11c could not be reduced in practical yield, apparently due to product inhibition of the catalyst. Asymmetric transfer hydrogenation of the aniline imine 8a was possible, but required impractical purity levels for the substrate, and the nitro analogue 7 could not be reduced efficiently. The best results were obtained with the bromophenyl imine 20. In the case of 20b, the product 21b was formed with 98.7% ee, and the material could be upgraded to >99% ee by crystallization of the hydrochloride salt. Reaction of 21b with NH3 or MeNH2 in the presence of Cu/CuCl gave the chiral anilines 10b or 23b. The latter substance is comparable to the commercially available 1 as a chiral proton donor for amide enolates and provides access to the hitherto unavailable enantiomeric series.