1987
DOI: 10.1002/jhet.5570240352
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Synthesis of novel 1‐phenyl‐1H‐indole‐2‐carboxylic Acids. I. Utilization of ullmann and dieckmann reactions for the preparation of 3‐hydroxy, 3‐alkoxy, and 3‐alkyl derivatives

Abstract: Methods for the synthesis of novel 3‐hydroxy, 3‐alkoxy, and 3‐alkyl indole‐2‐carboxylic acids and esters are described. Dieckmann cyclization of various 2‐[(carboxymethyl)amino]benzoic acid diesters yielded 1‐unsubstituted‐, 1‐methyl‐, and 1‐phenyl‐3‐hydroxy‐1H‐indole‐2‐carboxylic acid esters. An Ullmann reaction with bromobenzene converted 1H‐indoles to 1‐phenylindoles.

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Cited by 36 publications
(5 citation statements)
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“…Filtration followed by concentration in vacuo and recrystallization from ethyl acetate/hexane gave 235 mg (80%) of 23. An analytical sample was obtained by a second recrystallization from ethyl acetate/hexane: mp 143-143.5 °C; NMR (DMSO-de) ó 1.21 (d, =7 = 6.5 Hz, 6H), 3.41 (heptet, =7 = 6.5 Hz, 1H), 3.87 (s, 3H), 7.18 (dd, =7 = 9, 2.5 Hz, 1H), 7.42 5-Methoxy-3-(phenylthio)benzo[b]thiophene-2-carboxamide (24). Thiophenol (116 «L, 1.13 mmol) was added to a suspension of 22 (250 mg, 1.03 mmol) in 2 mL of dimethylformamide.…”
Section: Discussionmentioning
confidence: 99%
“…Filtration followed by concentration in vacuo and recrystallization from ethyl acetate/hexane gave 235 mg (80%) of 23. An analytical sample was obtained by a second recrystallization from ethyl acetate/hexane: mp 143-143.5 °C; NMR (DMSO-de) ó 1.21 (d, =7 = 6.5 Hz, 6H), 3.41 (heptet, =7 = 6.5 Hz, 1H), 3.87 (s, 3H), 7.18 (dd, =7 = 9, 2.5 Hz, 1H), 7.42 5-Methoxy-3-(phenylthio)benzo[b]thiophene-2-carboxamide (24). Thiophenol (116 «L, 1.13 mmol) was added to a suspension of 22 (250 mg, 1.03 mmol) in 2 mL of dimethylformamide.…”
Section: Discussionmentioning
confidence: 99%
“…5-Chloro- and 6-chloro-substituted 2-[1-(4-fluorophenyl)-1 H -indol-3-yloxy]acetic acids ( 17 ) were prepared in a two-step procedure from corresponding methyl 1-(4-fluorophenyl)-3-hydroxy-1 H -indole-2-carboxylates ( 16 ), which were prepared as described in the literature. , Alkylation of substituted methyl 1-(4-fluorophenyl)-3-hydroxy-1 H -indole-2-carboxylates ( 16 ) with methyl bromoacetate gave the corresponding methyl 2-[1-(4-fluorophenyl)-2-(methoxycarbonyl)-1 H -indol-3-yloxy]acetates . These diesters were hydrolyzed and subsequently decarboxylated to give the corresponding 2-[1-(4-fluorophenyl)-1 H -indol-3-yloxy]acetic acids ( 17 ).…”
Section: Chemistrymentioning
confidence: 99%
“…Preparation of Bicyclic Heteroarylpiperazines. Literature methods were adopted for the preparation of the 3-piperazinyl derivatives of the 1,2-benzisothiazole and N -phenylindole systems, with the following exceptions. For the preparation of 1-(6-chloro-1,2-benzisothiazol-3-yl)piperazine, the requisite 3-hydroxy-6-chloro-1,2-benzisothiazole was prepared as follows.…”
Section: Chemistrymentioning
confidence: 99%
“…For the preparation of 1-(6-fluoro-1-phenyl-1 H -indol-3-yl)piperazine, we utilized an alternative route which avoided the use of potassium cyanide. The Ullmann reaction of N -phenylglycine and 2-chloro-4-fluorobenzoic acid provided the intermediate diacid 70c in one step …”
Section: Chemistrymentioning
confidence: 99%