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3,3-Pentamethylene oxaziridine 1 forms an N-N bond with secondary isoquinoline bases 2a-f to give the cyclohexylidene hydrazines 3a-f.In some cases nitrogen elimination yielding indane derivatives 13b, 13e competes with hydrazone formation.The cyclic Schiff’base 14 and the beta-carboline derivative 16 can also be aminated.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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An electrochemically promoted coupling of benzoxazoles and amines has been developed, leading directly to the formation of 2-aminobenzoxazoles. The chemistry utilizes catalytic quantities of a tetraalkylammonium halide redox catalyst and is carried out under constant current conditions in a simple undivided cell. The use of excess chemical oxidant or large amounts of supporting electrolyte is avoided. This greatly simplifies the workup and isolation process and leads to a reduction in waste. (Chemical Equation Presented).

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1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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A series of pyrrolo[2,1-a]isoquinoline and coumarin-fused pentacyclic derivatives were synthesized via base-mediated divergent annulation of 4-chloro-3-formylcoumarin and tetrahydroisoquinoline as a key step. This method was then extended to the preparation of isolamellarins A and B (isolamellarin G trimethyl ether). When exposed to UV light, the pyrrolo[2,1-a]isoquinoline- and coumarin-fused pentacycles B were found to undergo aerobic oxidation to give the corresponding hydroxypyrrolones.

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Tetrahydroisoquinoline – Wikipedia,
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Eight tetrahydroisoquinoline alkaloids have been crystallized and identified from the nonphenolic and phenolic extracts of the giant Mexican cereoid cactus, Pachycereus weberi (Coult.) Br. and R.The identities were established as 5,6,7-trimethoxy-1,2,3,4-tetrahydroisoquinoline (nortehuanine) 1; 7,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline (lemaireocereine) 2; 7-methoxy-1,2,3,4-tetrahydroisoquinoline (weberidine) 3; 5,6,7,8-tetramethoxy-1,2,3,4-tetrahydroisoquinoline (weberine) 4; 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (heliamine) 5; 2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (N-methylheliamine or oxymethylcorypalline) 6; 2-methyl-5,6,7-trimethoxy-1,2,3,4-tetrahydroisoquinoline (tehuanine) 7; and 1,2-dimethyl-6,7-dimethoxy-8-hydroxy-1,2,3,4-tetrahydroisoquinoline (pellotine) 8.Compounds 1-4 have not been identified previously as natural compounds, while compounds 5-8 are previously known cactus alkaloids.Key Word Index – Lemaireocereus weberi; Pachycereus weberi; Stenocereus weberi; Cactaceae; tetrahydroisoquinoline alkaloids; lemaireocereine; weberine; weberidine; nortehuanine; tehuanine; heliamine; N-methylheliamine; oxymethylcorypalline; pellotine.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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The catalytic asymmetric addition of dialkylzinc to a carbon-nitrogen double bond in 3,4-dihydroisoquinoline N-oxides was achieved by utilizing a catalytic amount of 2-magnesium 3-zinc salt of dicyclopentyl (R,R)-tartrate to afford (S)-1-alkyl-2-hydroxy-1,2,3,4-tetrahydroisoquinolines. In order to realize higher enantioselectivity, it was crucial to add the nitrones slowly into dialkylzinc in the presence of a catalytic amount of the 2-magnesium 3- zinc salt of (R,R)-tartrate.

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Tetrahydroisoquinoline – Wikipedia,
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Iridium-catalyzed acceptorless dehydrogenative coupling of tertiary amines and arylamines has been developed. A number of benzimidazoles were prepared in good yields. An iridium-mediated C-H activation mechanism is suggested. This finding represents a novel strategy for the synthesis of benzimidazoles.

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1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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The unmasking of primary amines via the heterocycloreversion of N-alkyl-2-azanorbornenes can be catalyzed by either copper(II) or a sulfonic acid based ion exchange resin which obviates the necessity of employing a reactive dienophile to trap the cyclopentadiene as it is produced.

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Tetrahydroisoquinoline – Wikipedia,
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Azomethine ylides generated by the decarboxylation of imines of a- amino acids and 2,2?- dipyridyl ketone undergo 1,5-electrocyclisation and subsequent aromatisation to generate 1,3- disubstituted-2-azaindolizines. Azomethine ylides generated from 1,2,3,4- tetrahydroisoquinoline and diarylidene acetone undergo 1,5-electrocyclisation and subsequent prototropic rearrangement, to give pyrrolo-5,6-dihydroisoquinolines.

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A number of tricyclic carboxamides have been synthesized and tested to evaluate their ability to reverse multidrug resistance in the CHRC/5 cell line.Among them the acridone derivatives were the most potent.A key feature is the presence of a dimethoxybenzyl or phenethylamine cationic site, separated from the tricyclic lipophilic part by a carbamoylphenyl chain.Optimization led to compounds 2 orders of magnitude more active than the prototype inhibitors verapamil and amiodarone.On the basis of in vitro and in vivo activities, 9,10-dihydro-5-methoxy-9-oxo-N-<4-<2-(1,2,3,4-tetrahydro-6,7-dimethoxyisoquinol- 2-yl)ethyl>phenyl>-4-acridinecarboxamide (84) has been selected for further development.

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Tetrahydroisoquinoline – Wikipedia,
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The invention concerns a combination comprising at least one 2-oxo-indole derivative of formula (I) in which R1 is selected from the group consisting of thienyl, imidazolyl and pyridyl, optionally substituted by (C1-C3) alkyl, A is a -CH2CO- o -SO2- group; R is selected from the group consisting of 6,7-dimethoxy-1,2,3,4- tetrahydroisoquinolinyl, 3,4-dimethoxy-benzylamino, (C1-C3)alkyl, benzyl or a pharmaceutically acceptable salt thereof and at least one antitumor drug. The combination is for use in the treatment of tumors, in particular glioblastoma multiforme (GBM), breast tumor and pancreatic tumor. The combination is effective in the treatment of resistant tumor forms.

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Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem