1,2-Dihydroisoquinolines-II

Brown, David W.; Dyke, S.F.

doi:10.1016/s0040-4020(01)99031-3

Cited by 28 publications

(13 citation statements)

References 11 publications

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“…Berbines and 8-oxoberbines possess a variety of physiological activities, including antitumor and anticancer activities. 1 Acid-catalyzed cyclizations of 1,2-dihydroisoquinolines 1 (X ) H 2 ) to berbines 2 and isocarbostyrils 1 (X ) O) to 8-oxoberbines 3 were studied by Huffman, 2 Battersby, 3 and Dyke 4 in the period 1960-1966. In 1970, Govindachari 5 reported the application of those methods to the synthesis of protoberberine alkaloids.…”

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confidence: 99%

Aryl Radical Cyclizations: One-Pot Syntheses of Protoberberine and Pavine Alkaloids

et al. 2000

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Treatment of 2-(2'-bromo-beta-phenethyl)isocarbostyrils 7 with AIBN-Bu(3)SnH in boiling benzene gave 8-oxoberbines 3 in good yields. A similar treatment of 2-(2'-bromo-beta-phenethyl)isoquinolinium bromides 6 and their nor- and homoanalogues (10,11) induced 6-, 5-, and 7-exo radical closures in a one-pot manner to give protoberberines 2, dibenzo[b,g]indolizidine 14a and, dibenzo[a, h]-1-azabicyclo[5.4.0]undecane 15a, respectively. A one-pot radical cyclization of 1-(2'-bromobenzyl)isoquinoline methiodide 18a gave a pavine alkaloid, (+/-)-algemonine (19a).

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confidence: 99%

Aryl Radical Cyclizations: One-Pot Syntheses of Protoberberine and Pavine Alkaloids

et al. 2000

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“…N ‐Phenethyl‐1,2‐dihydroisoquinolines, 2 , which can be prepared by LiAlH 4 reduction of isoquinolinium salts, 1 , have been converted to the corresponding berbines, 3 , in heated mineral acids. [ 70–73 ] It was reported by Dyke that acid‐treatment (conc. HCl) of carbostyril 4 , which can be prepared by oxidation of 1 with K 3 [Fe(CN) 6 ], afforded 8‐oxoberbines 5 , [ 72 ] as shown in Figure 2.…”

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confidence: 99%

“…[ 70–73 ] It was reported by Dyke that acid‐treatment (conc. HCl) of carbostyril 4 , which can be prepared by oxidation of 1 with K 3 [Fe(CN) 6 ], afforded 8‐oxoberbines 5 , [ 72 ] as shown in Figure 2. Dyke also reported a similar method for the preparation of 3 and 5 starting with disproportionation of 1 with alkali and ending up with the Pictet‐Spengler cyclization of the resultant 2 and 4 , respectively.…”

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confidence: 99%

Synthesis of indolo[2,1‐a]isoquinolines by CF₃COOH‐induced cyclization

Wada

Kurono

Senboku

et al. 2020

Journal of Heterocyclic Chem

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Indolo[2,1-a]isoquinoline alkaloids and related compounds have been known to have interesting biological activities, such as antileukemic and antitumor activities. We found that 1-(3,4-dimethoxyphenethyl)indole gave 2,3-dimethoxyindolo [2,1-a]isoquinoline and 1-(3,4-dimethoxyphenylacetyl)indole gave 2,3-dimethoxy-6-oxoindolo[2,1-a]isoquinoline, respectively, by an intramolecular cyclization carried out in boiling trifluoroacetic acid.

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“…Colorless crystals (36%); R f 0.55 (3% methanol–dichloromethane); mp 153–154°C (methanol) [42] (lit. [43] mp 158–159°C).…”

Section: Methodsmentioning

confidence: 99%

Synthesis of 8‐Oxoberbines and Related Benzolactams by Pd(OAc)₂‐Catalyzed Direct Aromatic Carbonylation

Miyazawa

Tokuhashi

Horibata

et al. 2013

Journal of Heterocyclic Chem

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A variety of alkoxy‐substituted benzolactams with a berbine or yohimbane skeleton were prepared from 1‐benzyl‐1,2,3,4‐tetrahydroisoquinolines or 1‐benzyl‐1,2,3,4‐tetrahydro‐β‐carbolines by a phosphine‐free Pd(II)‐catalyzed direct aromatic carbonylation in a Pd(OAc)2‐Cu(OAc)2 catalytic system. The site selectivity was compared with that of the carbonylation with Pd(OAc)2 or Pd(OAc)2·2 PPh3, respectively.

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1,2-Dihydroisoquinolines-II

Cited by 28 publications

References 11 publications

Aryl Radical Cyclizations: One-Pot Syntheses of Protoberberine and Pavine Alkaloids

Aryl Radical Cyclizations: One-Pot Syntheses of Protoberberine and Pavine Alkaloids

Synthesis of indolo[2,1‐a]isoquinolines by CF₃COOH‐induced cyclization

Synthesis of 8‐Oxoberbines and Related Benzolactams by Pd(OAc)₂‐Catalyzed Direct Aromatic Carbonylation

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1,2-Dihydroisoquinolines-II

Cited by 28 publications

References 11 publications

Aryl Radical Cyclizations: One-Pot Syntheses of Protoberberine and Pavine Alkaloids

Aryl Radical Cyclizations: One-Pot Syntheses of Protoberberine and Pavine Alkaloids

Synthesis of indolo[2,1‐a]isoquinolines by CF3COOH‐induced cyclization

Synthesis of 8‐Oxoberbines and Related Benzolactams by Pd(OAc)2‐Catalyzed Direct Aromatic Carbonylation

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Synthesis of indolo[2,1‐a]isoquinolines by CF₃COOH‐induced cyclization

Synthesis of 8‐Oxoberbines and Related Benzolactams by Pd(OAc)₂‐Catalyzed Direct Aromatic Carbonylation