268. The action of acyl cyanides on 2- and 1 : 2-substituted indoles. Part II. Derivatives of 2-o-aminophenylindole

Kiang, A. K.; Mann, Frederick G.; Prior, A. F.; Topham, A.

doi:10.1039/jr9560001319

Cited by 29 publications

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“…It is well‐known that indole‐fused quinazolines, indolo[1,2‐ c ]quinazolines exhibit biological activities such as antibacterial and antifungal properties (Scheme ) . Since the synthesis of indolo[1,2‐ c ]quinazolines by thermal cyclization of 2‐(2‐aminophenyl)indoles with acyl cyanides followed by HCl treatment, many synthetic methods for such a hybrid scaffold are well documented . Several groups have shown that indolo[1,2‐ c ]quinazolines can be formed by condensation of 2‐(2‐aminophenyl)indoles with aromatic aldehydes and subsequent treatment with powdered KMnO 4 for oxidative cyclization .…”

Section: Methodsmentioning

confidence: 99%

Copper‐catalyzed CN Coupling and Cyclization of 2‐(2‐Bromophenyl)‐1H‐indoles with Primary Amides Leading to Indolo[1,2‐c]quinazolines

Yoo

Dao

Cho

2018

Bulletin Korean Chem Soc

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It is well-known that indole-fused quinazolines, indolo [1,2-c]quinazolines exhibit biological activities such as antibacterial and antifungal properties (Scheme 1). 1,2 Since the synthesis of indolo [1,2-c]quinazolines by thermal cyclization of 2-(2-aminophenyl)indoles with acyl cyanides followed by HCl treatment, many synthetic methods for such a hybrid scaffold are well documented. 3,4 Several groups have shown that indolo[1,2-c]quinazolines can be formed by condensation of 2-(2-aminophenyl)indoles with aromatic aldehydes and subsequent treatment with powdered KMnO 4 for oxidative cyclization. 1,2,5 Such a hybrid scaffold formation was also exemplified by palladium-catalyzed cyclocarbonylation of bis(o-trifluoroacetamidophenyl)acetylene with aryl or vinyl halides and triflates 6 and cyclization of 1-(N-arylimino)indoles formed by additionelimination between indoles and N-aryltrifluoroacetimidoyl chlorides. 7 It is also reported that 2-(2-halophenyl)indoles are coupled and cyclized with (aryl)methaneamines, amidine hydrochlorides, and amino acids in the presence of a copper catalyst to give indolo [1,2-c]quinazolines. 8-10 Wang et al. recently reported on synthesis of indolo[1,2-c]quinazolines from N-{2-[(2-aminophenyl)ethynyl]phenyl}amides by ZnBr 2 -promoted domino hydroamination-cyclization. 11During the course of our continuing studies directed towards cyclization reactions, 12 we have identified several new synthetic methods for N-fused hybrid scaffolds. 13 Under these circumstances, this report describes coppercatalyzed coupling and cyclization of 2-(2-bromophenyl)-1H-indoles with primary amides leading to indole-fused quinazolines, indolo[1,2-c]quinazolines.Treatment of 2-(2-bromophenyl)-1H-indole (1a) with an equimolar amount of formamide (2a) in DMF at 130 C for 24 h in the presence of a catalytic amount of CuI (10 mol %) along with Cs 2 CO 3 afforded indolo[1,2-c]quinazoline (3a) in 10% isolated yield with several unidentifiable products (Table 1, entry 1). Higher reaction rate and yield were observed with further addition of L-proline as a ligand (entry 2). It is known that the catalytic system of CuI combined with L-proline effectively catalyzes coupling and cyclization of 2-bromobenzamides with terminal alkynes leading to 3-alkylideneisoindolin-1-ones. 14 The molar ratio of [2a]/[1a] affected the yield of 3a and the yield increased with the increase of the molar ratio up to 2.0 along with complete conversion of 1a (entry 3). Lower reaction temperature resulted in a decreased yield of 3a (entry 4). The reaction proceeded using other amino acids such as glycine, L-phenylalanine, N,N-dimethylglycine, and 4-hydroxy-Lproline in place of L-proline, but the yield of 3a was generally lower than that by the use of L-proline except for 4-hydroxy-L-proline, which exhibited similar activity as Lproline (entries 5-8).Among bases examined under the employed conditions, Cs 2 CO 3 was shown to be the base of choice (entries 3 and 9-11). When used with L-proline and Cs 2 CO 3 , copper catalysts such as CuCl, CuBr...

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Section: Methodsmentioning

confidence: 99%

Copper‐catalyzed CN Coupling and Cyclization of 2‐(2‐Bromophenyl)‐1H‐indoles with Primary Amides Leading to Indolo[1,2‐c]quinazolines

Yoo

Dao

Cho

2018

Bulletin Korean Chem Soc

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“…(7). An amount of 8.2 g of this ester was dissolved in 20 ml of ethanol and a solution of 2.5 g WaCN in 8 ml of water was added.…”

Section: Methodsmentioning

confidence: 99%

Chain Elongation of Aromatic Amino Acids: the Role of 2-Benzylmalic Acid in the Biosynthesis of a C₆C₄ Amino Acid and a C₆C₃ Mustard Oil Glucoside

Dörnemann¹,

Löffelhardt²,

Kindl³

1974

Can. J. Biochem.

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A chemical synthesis of specifically 14C-labelled 2-benzylmalic acid, hitherto unknown, was developed. 4-Phenylacetoacetate obtained by condensation of phenylacetyl chloride-1-14C with ethyl acetoacetate yielded 2-benzylmalic acid-2-14C after cyanohydrin reaction and hydrolysis.2-Benzylmalic acid-2-14C, administered to shoots of Nasturtium officinale and Barbarea vulgaris, was shown to be an efficient precursor of the aglucone moiety of the mustard oil glucoside gluconasturtiin. The incorporation of radioactivity agreed well with the values reported for incorporation of 3-benzylmalic acid, but was considerably higher than that obtained after application of L-phenylalanine-U-14C. A conversion of 2-benzylmalic acid into 3-benzylmalic acid and 2-amino-4-phenylbutyric acid could also be demonstrated. These findings provide the final evidence for a chain-lengthening mechanism leading to homologous amino acids as proposed by Underbill and Wetter in 1966.

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“…Methanesulfonic acid (100 mL) by heating to 80 o C, then phosphorus pentoxide (13.5 g) was added to it with stirring until it dissolved completely. The phenylhydrazone of 2-aminoacetophenone (10.0 g, 44.4 mmol) (Kiang et al, 1956) was slowly added maintaining the temperature between 80 and 100 o C. The solution was then further heated at 85 o C for 30 min. The reaction mixture was cooled to room temperature and poured over crushed ice containing sodium hydroxide (65.0 g).…”

Section: General Procedures For the Preparation Of 2-(oaminophenyl)indmentioning

confidence: 99%

Synthesis of mono, bis-2-(2-arylideneaminophenyl) indole azomethines as potential antimicrobial agents

et al. 2011

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A series of mono and bis 2-2-(arylidineaminophenyl)indole azomethines have been synthesized by a condensation reaction of 2-(2-amino phenyl) indole with various mono and diketones R-CO-R(l) /R-CO-X-CO-R(l) (1:1/2:1 ratio) in ethanol media. The synthesized azomethines were characterized via IR, (1)H-NMR, (13)C-NMR, MS and elemental analysis. The antimicrobial activity of these compounds against different bacteria and fungi was also evaluated.

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268. The action of acyl cyanides on 2- and 1 : 2-substituted indoles. Part II. Derivatives of 2-o-aminophenylindole

Abstract: The Action of Acyl Cyavtides 0% Indoles. Part I I . 1319 268. The Action of Acyl Cyanides on 2-and 1 : 2-Substituted Indoles. Part II.* Derivatives of 2-0-Aminophenylindole.

Cited by 29 publications

References 1 publication

Copper‐catalyzed CN Coupling and Cyclization of 2‐(2‐Bromophenyl)‐1H‐indoles with Primary Amides Leading to Indolo[1,2‐c]quinazolines

Copper‐catalyzed CN Coupling and Cyclization of 2‐(2‐Bromophenyl)‐1H‐indoles with Primary Amides Leading to Indolo[1,2‐c]quinazolines

Chain Elongation of Aromatic Amino Acids: the Role of 2-Benzylmalic Acid in the Biosynthesis of a C₆C₄ Amino Acid and a C₆C₃ Mustard Oil Glucoside

Synthesis of mono, bis-2-(2-arylideneaminophenyl) indole azomethines as potential antimicrobial agents

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268. The action of acyl cyanides on 2- and 1 : 2-substituted indoles. Part II. Derivatives of 2-o-aminophenylindole

Abstract: The Action of Acyl Cyavtides 0% Indoles. Part I I . 1319 268. The Action of Acyl Cyanides on 2-and 1 : 2-Substituted Indoles. Part II.* Derivatives of 2-0-Aminophenylindole.

Cited by 29 publications

References 1 publication

Copper‐catalyzed CN Coupling and Cyclization of 2‐(2‐Bromophenyl)‐1H‐indoles with Primary Amides Leading to Indolo[1,2‐c]quinazolines

Copper‐catalyzed CN Coupling and Cyclization of 2‐(2‐Bromophenyl)‐1H‐indoles with Primary Amides Leading to Indolo[1,2‐c]quinazolines

Chain Elongation of Aromatic Amino Acids: the Role of 2-Benzylmalic Acid in the Biosynthesis of a C6C4 Amino Acid and a C6C3 Mustard Oil Glucoside

Synthesis of mono, bis-2-(2-arylideneaminophenyl) indole azomethines as potential antimicrobial agents

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Chain Elongation of Aromatic Amino Acids: the Role of 2-Benzylmalic Acid in the Biosynthesis of a C₆C₄ Amino Acid and a C₆C₃ Mustard Oil Glucoside