Category: 52250-50-7

A one-pot synthesis of β-lactams was written by Miyake, Muneharu;Tokutake, Norio;Kirisawa, Makoto. And the article was included in Synthesis in 1983.Application In Synthesis of 1-Phenyl-3,4-dihydroisoquinoline This article mentions the following:

β-Lactams I and II (R = phthalimido, 4-ClC₆H₄O; R¹ = Ph, substituted Ph; R² = substituted Ph; R³ = Ph, O₂NC₆H₄) and III (R = phthalimido, 4-nitrophthalimido, 4-ClC₆H₄O, 4-ClC₆H₄; X = O, S) were obtained in 39-64% yield by treating RCH₂CO₂H with 4-MeC₆H₄SO₂Cl and R¹CH:NR², 3,4-dihydroisoquinolines, or 2-phenyl-5,6-dihydro-4H-thiazine or oxazine in a 1-pot reaction. In the experiment, the researchers used many compounds, for example, 1-Phenyl-3,4-dihydroisoquinoline (cas: 52250-50-7Application In Synthesis of 1-Phenyl-3,4-dihydroisoquinoline).

1-Phenyl-3,4-dihydroisoquinoline (cas: 52250-50-7) belongs to isoquinoline derivatives. Quinoline is a mancude organic heterobicyclic parent, an azaarene, an ortho-fused heteroarene and a member of isoquinolines. Other industrial applications include their use as corrosion inhibitors, preservatives, and as solvents for resins and terpenes.Application In Synthesis of 1-Phenyl-3,4-dihydroisoquinoline

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Substrate scope in the direct imine acylation of ortho-substituted benzoic acid derivatives: the total synthesis (±)-cavidine was written by Kitsiou, Christiana;Unsworth, William P.;Coulthard, Graeme;Taylor, Richard J. K.. And the article was included in Tetrahedron in 2014.HPLC of Formula: 52250-50-7 This article mentions the following:

The direct imine acylation (DIA) and subsequent cyclization of a range of imines with ortho-substituted benzoic acid derivatives is described. Variation in the coupling reagents, imine and benzoic acid were all examined The DIA procedure was also applied in the total synthesis of (±)-cavidine (I). In the experiment, the researchers used many compounds, for example, 1-Phenyl-3,4-dihydroisoquinoline (cas: 52250-50-7HPLC of Formula: 52250-50-7).

1-Phenyl-3,4-dihydroisoquinoline (cas: 52250-50-7) belongs to isoquinoline derivatives. Quinoline and its derivatives are widely used as fungicides, biological agents, antibiotics, alkaloids, dyes, rubber chemicals and flavoring agents. Lewis acid activation and nucleophilic attack can produce multiple regioisomers in quinolines and pyridines; isoquinolines generally only undergo attack at the 1-position.HPLC of Formula: 52250-50-7

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Identification of an imine reductase for asymmetric reduction of bulky dihydroisoquinolines was written by Li, Hao;Tian, Ping;Xu, Jian-He;Zheng, Gao-Wei. And the article was included in Organic Letters in 2017.Reference of 52250-50-7 This article mentions the following:

A new imine reductase from Stackebrandtia nassauensis (SnIR) was identified, which displayed over 25- to 1400-fold greater catalytic efficiency for 1-methyl-3,4-dihydroisoquinoline (1-Me DHIQ) compared to other imine reductases reported. Subsequently, an efficient SnIR-catalyzed process was developed by simply optimizing the amount of cosolvent, and up to 15 g/L 1-Me DHIQ was converted completely without a feeding strategy. Furthermore, the reaction proceeded well for a panel of dihydroisoquinolines, affording the corresponding tetrahydroisoquinolines (mostly in S-configuration) in good yields (up to 81%) and with moderate to excellent enantioselectivities (up to 99% ee). In the experiment, the researchers used many compounds, for example, 1-Phenyl-3,4-dihydroisoquinoline (cas: 52250-50-7Reference of 52250-50-7).

1-Phenyl-3,4-dihydroisoquinoline (cas: 52250-50-7) belongs to isoquinoline derivatives. Quinoline and isoquinoline skeletons are among the most attractive frameworks with a wide range of biological and pharmacological activities. Most traditional methods of generating isoquinoline do so via oxidative aromatization of dihydro- or tetrahydro-isoquinolines, usually offering some environmental or economic advantage.Reference of 52250-50-7

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Nitrilium salts in the synthesis of heterocyclic compounds was written by Munoz, G. Garcia;Lora-Tamayo, M.;Madronero, R.;Marzal, J. Martinez. And the article was included in Anales Real Soc. Espan., Fis. y Quim. (Madrid) in 1961.Application In Synthesis of 1-Phenyl-3,4-dihydroisoquinoline This article mentions the following:

The general reaction between a complex of a nitrile with SnCl₄ and β-halogenated aryl group was described. PhCH₂CH₂Cl and several RCN reacted to yield I (R and % yield given): H, 14; Me, 91 (b_0.3 57°); Et, 100 (b_0.5 76-7°); Cl₃C, O; Ph, 65 (b_0.7 139-40°); o-MeC₆H₄, 59; o-O₂NC₆H₄, 50 (m. 83-4°); m-O₂NC₆H₄, 48; p-O₂NC₆H₄, 23 (m. 119-21°); p-MeOC₆H₄, 8; 3,4(MeO)₂C₆H₃, 16; αC₁₀H₇, 26; β-C₁₀H₇, 60; PhCH₂, 55 (b_0.5 142°); p-MeOC₆H₄CH₂, 6. The use of 1-chloro(3,4-dimethoxyphenyl)-ethane as a halogenated compound gave the corresponding dimethoxy derivatives of I (R and % yield given): Me, 58 (m. 105-6°); Ph, 82 (m. 122-3°); PhCH₂, 80; 3,4-(MeO)₂C₆H₃CH₂, 21. 1-(R-substituted)-6,7-methylenedioxy-3-methyl-3,4-dihydroisoquinolines (II) were prepared by use of RCN and 1-(3,4-methylenedioxyphenyl)-2-bromopropane (III) (R and % yield given): Me, 75; Et, 64; MeOCH₂, 64; Ph, 53, m. 94-4.5°; p-MeOC₆H₄, 30, m. 98°; 3,4-(MeO)₂C₆H₃, 52; 3,4-(CH₂O₂)C₆H₃, 45, m. 121-2°; PhCH₂, 79; 3,4-(MeO)₂C₆H₃CH₂, 23. Use of 3,4-(MeO)₂C₆H₃CH₂CHMeBr instead of III gave the 6,7-dimethoxy-3-Me derivatives of I (R and % yield given): Me, 90; Et, 92; MeOCH₂, 60; Ph, 69, m. 101-3°; p-MeOC₆H₄, 32, m. 103-4°; 3,4-(MeO)₂C₆H₃, 17; 3,4-(CH₂O₂)C₆H₃, 12; o-O₂NC₆H₄ 7; m-O₂NC₆H₄, 50; PhCH₂, 64; 3,4-(MeO)₂C₆H₃CH₂, 30. The picrates of all the compounds were prepared and m.ps. given. Reaction of RCN with o-ClCH₂C₆H₄NH₂ gave corresponding 2-R derivatives of 3,4-dihydroquinazoline (IV) (R and % yield given): Me, 68, b_0.5 125-8°; Et, 92; Pr, 91, b_0.3 122-3°; MeOCH₂, 68; Ph, 86, m. 142-3°; p-MeOC₆H₄, 75, m. 178-9°; o-O₂NC₆H₄, 71, m. 94-5°; m-O₂NC₆H₄, 96, m. 224-5°; o-ClC₆H₄, 40, m. 108-9°; α-C₁₀H₇, 90, m. 152-3°; PhCH₂, 100, m. 130-1°; p-ClC₆H₄CH₂, 93, m. 125-6°. Similarly o-MeNHC₆H₄CH₂Cl was used to prepare the 1-Me derivatives of IV (R and % yield given): Me, 85, b_0.2 80-1°; Ph, 83, m. 113-14°; o-O₂NC₆H₄, 75, m. 131-2°; p-MeOC₆H₄, 80. Some derivatives of IV were dehydrogenated to give the corresponding quinazolines (R and m.p. given): Me, -; Ph, 104-5°; p-MeOC₆H₄, 95-6°; o-O₂NC₆H₄, 108-9°; p-ClC₆H₄, -; α-C₁₀H₇, m. 127-8°. In the experiment, the researchers used many compounds, for example, 1-Phenyl-3,4-dihydroisoquinoline (cas: 52250-50-7Application In Synthesis of 1-Phenyl-3,4-dihydroisoquinoline).

1-Phenyl-3,4-dihydroisoquinoline (cas: 52250-50-7) belongs to isoquinoline derivatives. Quinoline and its derivatives are widely used as fungicides, biological agents, antibiotics, alkaloids, dyes, rubber chemicals and flavoring agents. It protonates to form salts upon treatment with strong acids, such as HCl. It forms adducts with Lewis acids, such as BF3.Application In Synthesis of 1-Phenyl-3,4-dihydroisoquinoline

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

A one-pot synthesis of β-lactams was written by Miyake, Muneharu;Tokutake, Norio;Kirisawa, Makoto. And the article was included in Synthesis in 1983.Application In Synthesis of 1-Phenyl-3,4-dihydroisoquinoline This article mentions the following:

β-Lactams I and II (R = phthalimido, 4-ClC₆H₄O; R¹ = Ph, substituted Ph; R² = substituted Ph; R³ = Ph, O₂NC₆H₄) and III (R = phthalimido, 4-nitrophthalimido, 4-ClC₆H₄O, 4-ClC₆H₄; X = O, S) were obtained in 39-64% yield by treating RCH₂CO₂H with 4-MeC₆H₄SO₂Cl and R¹CH:NR², 3,4-dihydroisoquinolines, or 2-phenyl-5,6-dihydro-4H-thiazine or oxazine in a 1-pot reaction. In the experiment, the researchers used many compounds, for example, 1-Phenyl-3,4-dihydroisoquinoline (cas: 52250-50-7Application In Synthesis of 1-Phenyl-3,4-dihydroisoquinoline).

1-Phenyl-3,4-dihydroisoquinoline (cas: 52250-50-7) belongs to isoquinoline derivatives. Quinoline is a mancude organic heterobicyclic parent, an azaarene, an ortho-fused heteroarene and a member of isoquinolines. Other industrial applications include their use as corrosion inhibitors, preservatives, and as solvents for resins and terpenes.Application In Synthesis of 1-Phenyl-3,4-dihydroisoquinoline

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Substrate scope in the direct imine acylation of ortho-substituted benzoic acid derivatives: the total synthesis (±)-cavidine was written by Kitsiou, Christiana;Unsworth, William P.;Coulthard, Graeme;Taylor, Richard J. K.. And the article was included in Tetrahedron in 2014.HPLC of Formula: 52250-50-7 This article mentions the following:

The direct imine acylation (DIA) and subsequent cyclization of a range of imines with ortho-substituted benzoic acid derivatives is described. Variation in the coupling reagents, imine and benzoic acid were all examined The DIA procedure was also applied in the total synthesis of (±)-cavidine (I). In the experiment, the researchers used many compounds, for example, 1-Phenyl-3,4-dihydroisoquinoline (cas: 52250-50-7HPLC of Formula: 52250-50-7).

1-Phenyl-3,4-dihydroisoquinoline (cas: 52250-50-7) belongs to isoquinoline derivatives. Quinoline and its derivatives are widely used as fungicides, biological agents, antibiotics, alkaloids, dyes, rubber chemicals and flavoring agents. Lewis acid activation and nucleophilic attack can produce multiple regioisomers in quinolines and pyridines; isoquinolines generally only undergo attack at the 1-position.HPLC of Formula: 52250-50-7

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Identification of an imine reductase for asymmetric reduction of bulky dihydroisoquinolines was written by Li, Hao;Tian, Ping;Xu, Jian-He;Zheng, Gao-Wei. And the article was included in Organic Letters in 2017.Reference of 52250-50-7 This article mentions the following:

A new imine reductase from Stackebrandtia nassauensis (SnIR) was identified, which displayed over 25- to 1400-fold greater catalytic efficiency for 1-methyl-3,4-dihydroisoquinoline (1-Me DHIQ) compared to other imine reductases reported. Subsequently, an efficient SnIR-catalyzed process was developed by simply optimizing the amount of cosolvent, and up to 15 g/L 1-Me DHIQ was converted completely without a feeding strategy. Furthermore, the reaction proceeded well for a panel of dihydroisoquinolines, affording the corresponding tetrahydroisoquinolines (mostly in S-configuration) in good yields (up to 81%) and with moderate to excellent enantioselectivities (up to 99% ee). In the experiment, the researchers used many compounds, for example, 1-Phenyl-3,4-dihydroisoquinoline (cas: 52250-50-7Reference of 52250-50-7).

1-Phenyl-3,4-dihydroisoquinoline (cas: 52250-50-7) belongs to isoquinoline derivatives. Quinoline and isoquinoline skeletons are among the most attractive frameworks with a wide range of biological and pharmacological activities. Most traditional methods of generating isoquinoline do so via oxidative aromatization of dihydro- or tetrahydro-isoquinolines, usually offering some environmental or economic advantage.Reference of 52250-50-7

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Polyphosphate esters as synthetic agents. II. Bischler-Napieralski reaction by means of polyphosphate esters and synthesis of 5H-2-benzazepine derivatives was written by Kanaoka, Yuichi;Sato, Eisuke;Yonemitsu, Osamu;Ban, Yoshio. And the article was included in Tetrahedron Letters in 1964.Reference of 52250-50-7 This article mentions the following:

Polyphosphate ester (I, prepared from P₂O₅ and Et₂O in CHCl₃ and used in situ, 5 parts) refluxed with 3,4-R₂C₆H₂CH₂CH₂NHCOR’ (R = MeO, R’ = Me; R = MeO, R’ = Ph; R = H,R’ = Me; R = H, R’ = Ph) 0.5-1.5 h. yielded 78-89% of the corresponding dihydroisoquinolines. Similarly, 3,4-(MeO)₂C₆H₃(CH₂)₃NHCOR (R = H, Me, Ph) were cyclized to yield the corresponding benzazepines (II, R = H, Me, Ph) (III, IV, V), in 76, 63, and 93% (crude) yields, resp., reduced by NaBH₄ to the resp. dihydro compounds (VII, VIII, IX). Phys. data are tabulated (compound, m.ps. of base, picrate, perchlorate, and methiodide given): III, 165-6掳, 197-8掳, 234掳 (decomposition), 182-5掳; IV, 140-3掳, 183-4掳, 190-1掳, 190-1掳; V, -, 222掳 (decomposition), 246-7掳 (decomposition), 206-6.5掳 (decomposition); VII, 172-3掳, 197-8, -, -; VIII, 115-20掳 (b. 3掳), 163-5, -, -; IX, 114-15, -, -, -. In the experiment, the researchers used many compounds, for example, 1-Phenyl-3,4-dihydroisoquinoline (cas: 52250-50-7Reference of 52250-50-7).

1-Phenyl-3,4-dihydroisoquinoline (cas: 52250-50-7) belongs to isoquinoline derivatives. Being an analog of pyridine, isoquinoline is a weak base, with a pKa of 5.14. Lewis acid activation and nucleophilic attack can produce multiple regioisomers in quinolines and pyridines; isoquinolines generally only undergo attack at the 1-position.Reference of 52250-50-7

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Iridium-catalyzed asymmetric hydrogenation of cyclic iminium salts was written by Ji, Yue;Feng, Guang-Shou;Chen, Mu-Wang;Shi, Lei;Du, Haifeng;Zhou, Yong-Gui. And the article was included in Organic Chemistry Frontiers in 2017.Application of 52250-50-7 This article mentions the following:

An enantioselective hydrogenation of cyclic iminium salts has been successfully realized by employing [Ir(COD)Cl]₂ and chiral diphosphine ligands as catalyst, furnishing chiral N-alkyl tetrahydroisoquinolines and N-alkyl tetrahydro-尾-carbolines with up to 96% ee and 88% ee, resp. The hydrogenation provides a direct, simple and efficient protocol toward chiral tertiary amines. Meanwhile, asym. hydrogenation at the gram scale was also conducted smoothly without loss of reactivity and enantioselectivity. In the experiment, the researchers used many compounds, for example, 1-Phenyl-3,4-dihydroisoquinoline (cas: 52250-50-7Application of 52250-50-7).

1-Phenyl-3,4-dihydroisoquinoline (cas: 52250-50-7) belongs to isoquinoline derivatives. Being an analog of pyridine, isoquinoline is a weak base, with a pKa of 5.14. Isoquinoline-type alkaloids show biological activities similar to those of morphinane-, protoberberine-, and benzophenanthridine-type alkaloids.Application of 52250-50-7

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

The role of the aromatic ligand in the asymmetric transfer hydrogenation of the C=N bond on Noyori’s chiral Ru catalysts was written by Sot, Petr;Vilhanova, Beata;Pechacek, Jan;Vaclavik, Jiri;Zapal, Jakub;Kuzma, Marek;Kacer, Petr. And the article was included in Tetrahedron: Asymmetry in 2014.Application of 52250-50-7 This article mentions the following:

Only four types of dimeric precursors [RuCl₂(畏⁶-arene)]₂ for the synthesis of Noyori’s half sandwich diamine catalysts [RuCl(TsDPEN)(畏⁶-arene)] are com. available, yet so far no study has tried to systematically evaluate how these systems perform during an asym. transfer hydrogenation of various 3,4-dihydroisoquinolines (i.e., the typical substrates for Noyori asym. transfer hydrogenation benchmarks). Experiments combined with mol. modeling allowed us to assess their properties and formulate a hypothesis clarifying the difference in enantioselectivity of these systems. The synthesis of the target compounds was achieved using [N-[(1S,2S)-2-(amino-魏N)-1,2-diphenylethyl]-4-methylbenzenesulfonamidato-魏N](畏⁶-benzene)(chloro)ruthenium and related catalysts, [N-[(1S,2S)-2-(amino-魏N)-1,2-diphenylethyl]-4-methylbenzenesulfonamidato-魏N]chloro[(1,2,3,4,5,6-畏)-1,3,5-trimethylbenzene]ruthenium, [N-[(1S,2S)-2-(amino-魏N)-1,2-diphenylethyl]-4-methylbenzenesulfonamidato-魏N]chloro[(1,2,3,4,5,6-畏)-1-methyl-4-(1-methylethyl)benzene]ruthenium and [N-[(1S,2S)-2-(amino-魏N)-1,2-diphenylethyl]-4-methylbenzenesulfonamidato-魏N]chloro[(1,2,3,4,5,6-畏)-1,2,3,4,5,6-hexamethylbenzene]ruthenium. Starting materials included 3,4-dihydro-6,7-dimethoxy-1-(methyl)isoquinoline, 3,4-dihydro-1-(phenyl)isoquinoline. The enantiomeric excess of products was determined after derivatization with carbonochloridic acid (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester [(-)-menthyl chloroformate]. The title compounds thus formed included 3,4-dihydro-2(1H)-isoquinolinecarboxylic acid (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester derivatives In the experiment, the researchers used many compounds, for example, 1-Phenyl-3,4-dihydroisoquinoline (cas: 52250-50-7Application of 52250-50-7).

1-Phenyl-3,4-dihydroisoquinoline (cas: 52250-50-7) belongs to isoquinoline derivatives. Quinoline is a mancude organic heterobicyclic parent, an azaarene, an ortho-fused heteroarene and a member of isoquinolines. Isoquinoline-type alkaloids show biological activities similar to those of morphinane-, protoberberine-, and benzophenanthridine-type alkaloids.Application of 52250-50-7

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem