Synthesis and Pharmacological Activity of 3-(2-Pyrrolidinyl)indoles

Ga, Youngdale; Dg, Anger; Wc, Anthony; Jp, Davanzo; Me, Greig; Rv, Heinzelman; Hh, Keasling; Szmuszkovicz, Jacob

doi:10.1021/jm00334a006

Cited by 25 publications

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“…This compound has a high level of basicity and reactivity. The overall synthesis pathway of this compound is similar to that of Youngdale and its colleagues [4], but we managed to achieve higher efficiencies by controlling the temperature, time and pHand which provide more complete spectral data [9].…”

Section: Resultsand Discussionmentioning

confidence: 99%

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Tertiary cyclic amides in Vilsmeier type reaction with indoles

Aghazadeh

2019

Prog. Chem. Biochem. Res.

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Vilsmeier-Haack reaction also called Vilsmeier reaction was first used for the formylation of an active arene, during which a mixture of phosphorus oxychloride and dimethylformamide (Vilsmeier reagent) was added to N,N-dimethyl aniline [1].The reaction of indole with the Vilsmeier reagent, followed by base, is the classic and very efficient method for the 3-formylation of indoles (Scheme 1) [2]. Before the alkaline hydrolysis step, the product which was a salt, 3-[(dimethylamino)methylene]-3Hindolium chloride (1), was followed by a basic workup affording dimethylamine and aldehyde. 3-Acylindoles can be obtained from Vilsmeier reaction of indole and tertiary amides in combination to phosphorus oxychloride [3]. Scheme 1.The reaction of indole with Vilsmeier reagent for the 3-formylation of indoles

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Section: Resultsand Discussionmentioning

confidence: 99%

“…However, when 1-methylpyrrolidine-2-one is used as the cyclic amide component, 3-(1-methylpyrrolidin-2-ylidene)-3H-indole (3) can be the product, without forming any amino ketone product [4]. This compound contains an intriguing combination of enamine and imine (as part of 3H-indole) groups in conjugation.…”

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confidence: 99%

Tertiary cyclic amides in Vilsmeier type reaction with indoles

Aghazadeh

2019

Prog. Chem. Biochem. Res.

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“…For the original synthesis of 3-(1-methylpyrrolidin-2-ylidene)-3H-indole, see: Youngdale et al (1964). For a study of its extraordinarily high basicity, see: Harris & Joule (1978) and for examples of its synthetic applications, see: Bishop et al (1981Bishop et al ( , 1982; Al-Khawaja et al (1984).…”

Section: Related Literaturementioning

confidence: 99%

3-(1-Methylpyrrolidin-2-ylidene)-3H-indole sesquihydrate

Helliwell¹,

Aghazadeh²,

Baradarani³

et al. 2009

Acta Cryst E

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The asymmetric unit of the title compound, C13H14N2·1.5H2O, contains two similar molecules of 3-(1-methylpyrrolidin-2-ylidene)-3H-indole, (I), and three water molecules. (I) is the product of reacting indole with 1-methylpyrrolidin-2-one in the presence of phosphorus oxychloride. Both organic molecules are almost completely planar; the maximum distances above and below the least-squares plane through all the atoms of molecule 1 are 0.050 (8) and −0.045 (8) Å, respectively, and the deviations for molecule 2 are 0.096 (8) and −0.059 (8) Å, respectively. In the crystal, the two crystallographically different molecules alternate in π-stacked columns [centroid–centroid distances = 3.729 (5) and 3.858 (5) Å], which are linked by O—H⋯N hydrogen bonds to a network of hydrogen-bonded water molecules. O—H⋯O interactions are also present.

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“…2 However, when 1-methylpyrrolidin-2-one is used as the cyclic amide component, 3-(1-methylpyrrolidin-2-ylidene)-3H-indole (1) is the product, without formation of an amino ketone product (2) (Scheme 1). 3,4 Compound 1 contains an intriguing combination of enamine and imine (as part of a 3H-indole) groups in conjugation. Usually the primary products, resulting from the Vilsmeier-Haack acylation, are hydrolyzed immediately without isolation of the intermediate iminium salts.…”

Section: Introductionmentioning

confidence: 99%

Formation of indole trimers in Vilsmeier type reactions

Aghazadeh¹

2019

Arkivoc

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The reaction of indole with the complex formed from 1,3-dimethylimidazolidin-2-one or N-methyloxindole with phosphorus oxychloride (phosphoryl chloride), was studied. In similar reactions of five-membered tertiary amide rings, 3-(1-alkyl-pyrrolidin-2-ylidene)-3H-indoles or ring opening products were obtained but in these cases, new products N 1 ,N 2 -dimethyl-N 1 -[tri-(1H-indol-3-yl)methyl]ethane-1,2-diamine and N-methyl-2-(3,3,3-tri-(1H-indol-3-yl)propyl)aniline as trimers of indole were obtained.

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Synthesis and Pharmacological Activity of 3-(2-Pyrrolidinyl)indoles

Cited by 25 publications

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Tertiary cyclic amides in Vilsmeier type reaction with indoles

Tertiary cyclic amides in Vilsmeier type reaction with indoles

3-(1-Methylpyrrolidin-2-ylidene)-3H-indole sesquihydrate

Formation of indole trimers in Vilsmeier type reactions

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